All 274 Jay-Z Songs, Ranked From Worst to Best

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If Jay-Z had his way back in 1996, this list would be too brief to warrant compiling. The skinny kid from Brooklyn’s Marcy Projects intended to drop just one album — a musical I was here statement — before partnering with a major label and falling back into a comfy executive role, becoming a vessel to launch hopeful Roc-A-Fella acts like Memphis Bleek and Christión into orbit.

But the industry had different plans. Def Jam, impressed with Roc-A-Fella’s early independent success, agreed to sign a joint venture with the young imprint on one condition: They needed seven albums from Jay. And now, two decades (and two dozen solo LPs) later, Jay-Z has become one of music’s all-time most important voices. His catalogue contains some of the most potent imagery and lucid storytelling about poverty and the desperation that it breeds, all while dominating mainstream pop music, in a delicate tightrope act that almost no one else has ever been able to manage for the span of time that Jay has. His merging of thinking-man street raps with commercial hits paved the way for artists like Kendrick Lamar and J. Cole to do the same today.

Jay-Z’s adolescence coincided with the Reagan ’80s. He’d spend his time banging on the kitchen table at his 534 Flushing Avenue apartment, rhyming to the percussion he created. But as an adolescent, he put his hobby on the backburner and crack sales on the front. But he continued to develop his craft, taking stock of hip-hop’s evolving aesthetics and mastering hyperspeed raps in the vein of East Coast rap duo Das EFX. Jay moved in and out of rapper circles in the late ’80s and early ’90s, popping up on songs with his mentor, Jaz-O, and Big Daddy Kane. He’d adopt a slower, more conversational pace for his 1996 masterpiece debut LP, Reasonable Doubt, a project that was self-released after his undeniable talent was denied by every major label he approached.

He followed that with the inconsistent, overly polished In My Lifetime, Vol. 1, which took more than a few cues from the flashy rap aesthetic that Puff Daddy had been proliferating through his Bad Boy label. The sound fit Jay just as well as one of Biggie’s oversized Coogi sweaters might have — there are hints of genius, but he was clearly still finding his voice and place in the art form.

From 1998 through 2003, Jay was unstoppable. He released at least one project annually, while nurturing promising new talent like Philadelphia-based rappers Freeway and Beanie Sigel. With the help of brilliant music minds like Kanye West, Just Blaze, and the Neptunes, Jay dictated the course of hip-hop and emerged as a keen songwriter who knew exactly how to maximize the strengths of his collaborators. He released his career-defining LP The Blueprint in 2001 and released the excellent retirement fake-out The Black Album just two years later.

But Jay never really committed to his retirement. From 2004 on, he seemed hell-bent on proving that he still had what it took to keep the No. 1 spot. Every release from this period of his career had a strategic selling point, whether it was a marquee collaborator like R. Kelly, Kanye West, or Linkin Park, or a calculated buy-in — Kingdom Come and Budweiser, American Gangster and the film American Gangster, Magna Carta … Holy Grail and Samsung. These albums range from lyrically and musically progressive, to painfully awkward and unfocused.

Maybe it’s too early to determine, but Jay-Z’s latest album, the confessional 4:44, seems to be the start of a new phase in the rapper’s career. It’s a human album that builds on familiar topics like black nationalism, infidelity, and money phones, but here, he handles these topics with more maturity and sophistication than ever before.

The expensive, No I.D.–chopped samples — Nina Simone, Stevie Wonder, Sister Nancy, the Fugees — are significant in their own right, creating a mature and well-worn ambiance unlike anything else streaming on Spotify’s RapCaviar playlist. 4:44 is the late-career big-budget home run that Hov needed.

So what’s next for Jay-Z? It’s never been harder to predict where he’s headed musically — which is why it’s the perfect time to look back on his entire body of work. Below, you’ll find a comprehensive listing of Jay-Z’s songs with some parameters for manageability: no freestyles over someone else’s beats (sorry “Young, Gifted and Black”), no song in which Jay-Z is not the lead artist (unless it appears on a DJ compilation). No leaked tracks, no mash-ups, and no remixes — a tricky restriction given Jay’s penchant for sequels.

Before we get into it, props are due to Sean Fennessey — and by extension, DJ Clark Kent — whose 2008 Jay-Z songography for Vibe magazine was a crucial cornerstone of this list’s creation.

Here’s Jay-Z’s full canon (so far), from most regrettable — two albums with R. Kelly! — to most remarkable.

274. “Anything,” Kingdom Come (2006): Jay-Z’s first ever collaboration with Usher is an ode to amateur night at the strip club.

273. “Tru Life Intro,” Tru York (2007): Hov spends two minutes firing spoken subliminal shots at Cam’ron and Jim Jones, and introducing the world to rapper Tru Life. The final minute features some struggle patois and one of Jay’s most throwaway of throwaway freestyles.

272. “Bitches & Sisters,” The Blueprint²: The Gift & the Curse (2002): At best, this N.W.A-sampling cut is a misguided attempt at celebrating stand-up women and shaming shady ones. At worst, it’s an indefensible cocktail of misogyny and respectability politics that Jay for some reason made sure to retain as a bonus cut on the abridged rerelease Blueprint 2.1.

271. “Nickels and Dimes,” Magna Carta … Holy Grail (2013): Hov expresses his side in a squabble over social responsibility with civil-rights icon Harry Belafonte that should’ve never happened. We could’ve done without this song, too.

270. “I Know What Girls Like,” In My Lifetime, Vol. 1 (1997): Ah, yes, the phase when Jay-Z was blinded by Puff Daddy’s shiny suits. Who decided it was a good idea to crate dig in the Waitresses’ catalogue?

269. “La Familia,” Magna Carta … Holy Grail (2013): Keep the phrase “facts only” and Lil Wayne jab, delete the rest.

268. “Pretty Girls,” Unfinished Business (2004): In 2002, Jay-Z and R. Kelly joined forces for The Best of Both Worlds, an unprecedented duet album uniting two hip-hop and R&B giants. The project was doomed, though, once a video that allegedly shows the Chicago singer having sex with (and urinating on) an underage girl began making the rounds — Jay wisely fell back from the project like Homer Simpson sinking into a bush. The controversy seemed to be simmering down two years later (despite 14 then-pending child-pornography charges against Kelly in Chicago) and the two stars gave it another go. Still, after “that VHS tape,” the title and subject matter of this generic song should’ve raised a red flag.

267. “As One,” The Blueprint²: The Gift & the Curse (2002): A rip-off of Earth, Wind & Fire’s “Fantasy” that serves as a roll call for Roc-A-Fella’s newly bolstered roster. Maurice White deserved better.

266. “Shorty,” The Best of Both Worlds (2002): R. Kelly sings about sexing “pretty girls” from coast to coast — and specifically cities like New York, Los Angeles, and Miami. The following year, Kelly was actually arrested in Miami after police found 12 images of a nude, underage girl in his Florida home. Those child-pornography charges were later dropped after a technicality deemed the photos inadmissible in court. But yeah, this song is okay, I guess.

265. “2 Many Hoes,” The Blueprint²: The Gift & the Curse (2002): Jay’s second Blueprint album is weighed down by filler songs like this male groupie shooing.

264. “Reminder,” The Blueprint 3 (2009): Hov re-reintroduces himself by running down his résumé in a meticulous manner and demanding that fans, peers, and bloggers put some respek on his name. Singer K. Briscoe’s hook is robotic and irksome.

263. “Hollywood,” Kingdom Come (2006): A stripped-down, Beyoncé-led version of this track appears on the deluxe version of her album B’Day, which dropped months earlier. “Hollywood” fits much better there — too much woe-is-me fame bemoaning from Jay on an already out-of-touch Kingdom Come.

262. “Jockin’ Jay-Z (Dopeboy Fresh),” B-side (2008): Even Jay’s most loyal fans act as if this holdover from The Blueprint 3 never happened. Kanye’s hyperventilating synths and Run-DMC sample are ill-fitting for Hov. If nothing else, the track delivers a needed response after Noel Gallagher disparaged his 2008 Glastonbury Festival headlining slot: “That bloke from Oasis said I couldn’t play guitar / Somebody shoulda told him I’m a fucking rock star.”

261. “Venus vs. Mars,” The Blueprint 3 (2009): Jay may have been reading too many self-help books.

260. “Things That U Do,” Vol. 3… Life and Times of S. Carter (1999): Long before Future and Drake made the flute hip-hop’s hottest instrument of 2017, Swizz Beatz programmed this basic woodwind melody for a contrived attempt at a hit record.

259. “She’s Coming Home With Me,” Unfinished Business (2004): An unnecessary revisiting of the stronger “Somebody’s Girl” from two years earlier. Hey, did you know that R. Kelly has been running what’s been described as an abusive and manipulative sex cult at his homes in Georgia and Illinois, according to an extensively reported BuzzFeed exposé?

258. “S. Carter,” Vol. 3… Life and Times of S. Carter (1999): From the music to the lyrics, this song feels limp. Aside from being a vehicle to showcase Amil, who already has two other appearances on this album, it really has no reason to exist.

257. “Off That,” The Blueprint 3 (2009): In the early 2000s, Jay-Z popularized and then killed the trend of wearing retro Mitchell & Ness jerseys in favor of another fashion fad: button-up shirts. He must’ve become a bit high on his own influence. It’s the only way to explain this silly Drake-sponsored attempt to buck some more trends — from Timberland boots to money showers at the strip club.

256. “Young Forever,” The Blueprint 3 (2009):

In this song’s defense, it goes down much smoother when performed live, with Beyoncé singing the hook in place of Mr. Hudson. Still, Jay should stay away from ’80s pop samples. And Mr. Hudson.

255. “Break Up (That’s All We Do),” Unfinished Business (2004): Another recycled concept from The Best of Both Worlds that adds nothing new to its predecessor (“Break Up to Make Up”). Even the titles are nearly identical, ugh.

254. “Stranded (Haiti Mon Amour),” Hope for Haiti Now (2010): A charity track in support of survivors of the devastating 2010 earthquake in Haiti. Jay-Z syncs up with Rihanna and U2’s Bono and the Edge for a sincere dedication. Musically, the sum is not greater than its parts.

253. “Versus,” Magna Carta … Holy Grail (2013): Jay nods to A Tribe Called Quest on this quickie of an interlude that has promise, but is too brief to ever really establish itself.

252. “The Return,” Unfinished Business (2004): Jay has better Slick Rick impressions in his catalogue.

251. “H.O.V.A.,” The Desert Storm Mixtape: DJ Envy Blok Party Vol. 1 (2003): Yet another name-based anthem that uses a hollering vocal sample to big-up Jay, who in return drops a freestyle that sounds like he’s just fooling around.

250. Dig a Hole,” Kingdom Come (2006): This retort to Cam’ron’s caustic “You Gotta Love It” puffs out its chest and builds the anticipation for a dismantling, but in the end it’s just a slap on the wrist.

249. “Lookin’ at My S Dots” (2003): To think, this glorified Reebok ad would’ve graced The Black Album in place of the legend-making “Public Service Announcement (Interlude)” if not for an eleventh-hour spurt of inspiration from Just Blaze. “Lookin’ at My S Dots” is fine as a one-minute short, but it would’ve dated the LP with of-the-moment references to NBA ballplayers Kenyon Martin and Shawn Marion.

248. “Blue’s Freestyle/We Family,” 4:44 (2017): Come for Blue Ivy’s mumble raps (that flow, though!); stay for Jay deriding Trump and pledging the importance of kin while a sample of Colombian singer Totó la Momposina’s voice plays in the background. This bonus track is a decent addition to 4:44, but sits among the project’s weaker material.

247. “Big Chips,” Unfinished Business (2004): After canceling their first collaborative album, Jay and Kelly never came close to recapturing their magic from classics like “Fiesta (Remix),” although this horn-laden single tries its best.

246. Pussy,” The Best of Both Worlds (2002): Songs like this make you wonder what was discussed during this album’s in-studio brainstorming sessions. After Kellz and Jay tell cautionary tales about man’s carnal weakness, Devin the Dude shares an anecdote about losing his virginity at age 7.

245. “You’re Welcome” (2008): “This is much more than marketed music,” Jay-Z raps on a languid Mary J. Blige–featuring track recorded to boost anticipation for their co-headlining Heart of the City tour that year. You might believe him, if a usually high-energy Swizz didn’t sound so dry on this overall meh loosie.

244. “We Got Em Goin,” Unfinished Business (2004): Memphis Bleek and Jay add some flair to an insipid album cut with a bridge in which they complete each other’s rhymes for four bars over a beat switch-up.

243. “Pop 4 Roc,” Vol. 3… Life and Times of S. Carter (1999): A passable Roc-A-Fella posse cut that feels more like a team-building exercise. Check out Amil’s “4 Da Fam,” released one year later for the real deal.

242. “Shake Ya Body,” The Best of Both Worlds (2002): Trackmasters’ synth chirps and Lil Kim’s repetitive chorus make this a guilty-pleasure earworm.

241. “For My Thugs,” The Tunnel (1999): A lukewarm Roc-A-Fella family affair that unites Memphis Bleek, Beanie Sigel, Jay-Z, and Amil. As it’s title suggests, it’s a gritty episode, best depicted by this callous threat from Hov: “Running the streets, lawless, blastin’ police / Sticking Furby’s out the window, snatchin’ your niece.”

240. “Roc Army,” Paid in Full Soundtrack (2002): A sparse Roc cross-pollination designed to unite Cam’ron with State Property, under Jigga’s supervision. The verses are choppy and the song is mostly bloated with soundbites from older material.

239. “The City Is Mine,” In My Lifetime, Vol. 1 (1997): The eulogy to late friend Biggie Smalls feels heartfelt, but Jay’s posturing as rap’s next in line here is unconvincing.

238. “Trouble,” Kingdom Come (2006): There’s some pretty harsh subliminal sniping at unnamed targets in the closing verse, but this song is probably best remembered as a hint of the impending release of “4:44,” 11 years early. “If my hand’s in the cookie jar, know one thing / I’ma take the cookie, not leave my ring,” he rhymes over Dr. Dre’s staticky instrumental.

237. “(Always Be My) Sunshine,” In My Lifetime, Vol. 1 (1997): Foxy Brown and Jay-Z’s glitzy follow-up to “Ain’t No Nigga” misses its mark, badly. The song reeks of trendy pandering; the polychromatic music video, with its fish-eye camerawork, is a Top 10 corniest Hov moment.

236. “Feelin’ You in Stereo,” Unfinished Business (2004): Well, this sure is meta. R. Kelly sings about trying to conjure the sexiest lyrics and music possible for this actual song, and Jay enables him by dropping eight bars of metaphors about waistlines and bass lines. It’s not terrible, though, just too goofy for anyone’s sex playlist.

235. “Lift Off,Watch the Throne (2011): Kanye West and Jay-Z held a listening session for Watch the Throne at the American Museum of Natural History’s Hayden Planetarium. As the album played, attendees watched an outer-space light show, with shooting stars zipping across an overhead screen. The setting particularly amplified this galactic Beyoncé-guested track, despite Kanye’s verse sounding like placeholder vocals and Hov not saying much of anything, either.

234. “Mo’ Money,” Unfinished Business (2004): Another phoned-in update of a superior Best of Both Worlds track (“Get This Money”) and a spectacular example of why sometimes more is less.

233. “What They Gonna Do” / “What They Gonna Do Part II,” The Blueprint²: The Gift & the Curse (2002): Shawn Carter flirts with dancehall — at the time a scalding-hot mainstream fascination — but stops short of fully committing musically. The alternate version retains his verses, but backpedals by swapping out Sean Paul’s vocals and adding a Timbaland beat that possesses not even a sprinkle of jerk seasoning.

232. “Stop,” Unfinished Business (2004): Kellz reignites an odd R&B beef with Sisqo, while Foxy and Jay drop solid verses without a single mention of Bonnie or Clyde.

231. “I Made It,” Kingdom Come (2006): A saccharine dedication to Jay-Z’s mother that’ll make you say “aww” but probably will never listen to again.

230. “All Around the World,The Blueprint²: The Gift & the Curse (2002): While there’s nothing especially wrong with this atlas-scanning cut, it’s the type of bland fodder that prevented The Blueprint² from living up to its predecessor.

229. Fuck All Nite,” The Blueprint²: The Gift & the Curse (2002): A Pharrell-guested track that’s good for a nice, mindless two-step and not much else.

228. “Holy Grail,” Magna Carta … Holy Grail (2013):

Justin Timberlake’s melodramatic singing about the pitfalls of fame borders on comical.

227. “Nigga Please,” The Blueprint²: The Gift & the Curse (2002): A checklist of riches, accolades, and overall bragging rights over a forgettable beat from Pharrell and Chad Hugo.

226. “Tom Ford,” Magna Carta … Holy Grail (2013): “I don’t pop molly, I rock Tom Ford” is one of rap’s great non sequiturs.

225. “20 Bag Shorty,” The Projects Presents: Balhers Forever (2000): Jay’s braggadocio is impeccable on this deep cut that’s likely only recognizable to stans.

224. “Don’t Let Me Die,” Unfinished Business (2004): An impassioned soul-baring prayer from Robert Kelly — who’s obviously been battling demons for some time now — on an otherwise uninspired project.

223. BBC,” Magna Carta … Holy Grail (2013): Justin Timberlake, Pharrell, Nas, Timbaland, Swizz Beatz, and Jay-Z put their heads together and came up with this tepid ode to ’80s drug-dealer paraphernalia.

222. “They Don’t Love You No More,” I Changed a Lot (2015):

Sports fans gave Jay (perhaps unwarranted) shit for the line, “Boy, you know you soft as a lacrosse team” — a perceived Drake diss — pointing out that lacrosse is indeed a full-contact sport. Still, Hov fit right in over ringing gongs on his first proper DJ Khaled collaboration alongside Rick Ross, French Montana, and Meek Mill.

221. “Girl’s Best Friend,” Vol. 3… Life and Times of S. Carter (1999): Jay personifies diamonds to fit the plot of the cop comedy Blue Streak (this song also appears on the soundtrack). But this cut seems more like cubic zirconia compared to harder Swizz-produced singles of the era (i.e., “Money, Cash, Hoes”).

220. “Wishing on a Star,” In My Lifetime, Vol. 1 (1997): The cover of Rose Royce’s song of the same name sounds flat, but this is a warm recollection of childhood’s innocent days. There’s no talk of Jay’s hustler past here — a rarity — but instead he recalls cutting school, playing run, catch and kiss, and imitating his favorite rappers in the mirror, armed with a brush as a microphone.

219. “Paper Chase,” Vol. 2… Hard Knock Life (1998): On wax, Foxy Brown makes for a convincing Bonnie to Jay-Z’s Clyde. Still, it’s awkward to listen back on their old collabos now that she’s been replaced by his real-life spouse, who also happens to be the world’s most famous pop star.

218. “Justify My Thug,” The Black Album (2003): This revision of Madonna’s “Justify My Love” fittingly gets flack as The Black Album’s weak link. It is a curious choice for a remake, but DJ Quik’s synthesizer rounds out the album with a catchy Cali bounce.

217. “Beach Is Better,” Magna Carta … Holy Grail (2013): At under a one-minute runtime, this is a missed opportunity for a playful, fly-on-the-wall look inside the Carter household. Still, “Girl, why you never ready?” is a delicious “They’re just like us!” moment.

216. “Hate,” The Blueprint 3 (2009): Some of the inflections are weird, but Kanye wins this kooky pre–Watch the Throne track with some amusing laser-gun and car-engine onomatopoeias.

215. “Hello Brooklyn 2.0,” American Gangster (2007): Lil Wayne and his idol address the borough of Brooklyn as a woman, with help from a significant Beastie Boys sample. Not quite the best-rapper-alive lyrical showdown that rap heads craved in ’07 (that’d come via Weezy’s “Mr. Carter” the following year) but this still has a nice bounce to it.

214. “A Dream,” The Blueprint²: The Gift & the Curse (2002): The allure of this dialogue from beyond with the Notorious B.I.G. wears off after the first listen, but props to Jay for finding new ways to keep Biggie’s legacy alive.

213. “Get Your Mind Right Mami,” The Dynasty: Roc La Familia (2000): Singer Rell was an underused member of the Roc; but here he helps Snoop, Bleek, and Jay’s pimp talk go down easier.

212. “F.U.T.W.,” Magna Carta … Holy Grail (2013): Jay-Z sure knows how to blow his own horn. Here he presents his unlikely success as a disruptive force, likening himself to Muhammad Ali and Dr. Martin Luther King Jr. How could you not root for this guy?

211. “Real Niggaz,” In My Lifetime, Vol. 1 (1997): There’s a historical significance here: Jay invites Too $hort along as his first rap collaborator from beyond the Big Apple, following a model Biggie established on Life After Death (which also features the Bay Area rapper, among other regional stars). Still, this beat is plodding, and the track slows the momentum of Vol. 1’s back half.

210. “Hova Song (Intro)” / “Hova Song (Interlude)” / “Hova Song (Outro),” Vol. 3… Life and Times of S. Carter (1999): Jay accomplishes a lot in the space of three brief free-form rhymes over an eerie K-Rob instrumental: He snaps at 50 Cent, compares himself to a pre-Russiagate Donald Trump, and maintains his stance as a rap deity, asking, “Do you believe? It’s Hova the God.”

209. “I Did It My Way,” The Blueprint²: The Gift & the Curse (2002): Frank Sinatra is one of Hov’s favorite figures to emulate; he likens himself to the legendary singer with Mafia ties by sampling his 1969 classic “My Way” — albeit the less-popular Paul Anka version (it was cheaper to clear than Sinatra’s).

208. “A Star Is Born,” The Blueprint 3 (2009): This song finds Jay chronicling the rise and runs of his peers and neophytes. It approaches gimmicky ground when he introduces his own rap prospect, but J. Cole seizes his moment with the song’s hottest internal rhyme: “The flow’s cold as the shoulders / Of gold-digging hoes / When a broke nigga approaches.”

207. “The Game Is Mine,” Creative Control (2010): Green Lantern recorded and jumbled sounds from a live tennis match for what was intended to be a Reebok ad on wax. Instead it became a stand-alone short that finds Hov announcing his partial ownership of the Brooklyn Nets.

206. “Get This Money,” The Best of Both Worlds (2004): This sounds like every song about life on the other side of the club’s VIP rope.

205. “History,” More Than a Game Soundtrack (2008): Somewhere within this muddled and vague extended metaphor about success, defeat, victory, death, and history, Jay is trying to congratulate Barack Obama for becoming America’s first black president, I think.

204. “Moonlight,” 4:44 (2017):

There are some important messages about the struggle of being a black creative on here, mixed with ideas on acceptable Instagram etiquette, according to Shawn Corey Carter. Unfortunately, the Fugees-sampling beat is the Ambien-induced version of DJ Khaled’s “Nas Album Done,” and Jay raps like he’s reading Blue Ivy a bedtime story.

203. “It Ain’t Personal,” The Best of Both Worlds (2002): Jay and R. Kelly express the confusion that comes with fake friends, both sounding conflicted. This simile from Hov still evokes a chuckle, though: “And your mom got it twisted, she think Hov changed / Nope, Hov’s still here like Rogaine.”

202. “Guns and Roses,” The Blueprint²: The Gift & the Curse (2002): Rap-rock hybrids can be tricky to pull off, but Lenny Kravitz blends in nicely on this one (their 2004 collabo “Storm” is even funkier). Unfortunately, Hov tries to kick knowledge but instead offers questionable optimism: “Even a garbage can gets a steak,” he raps, a failed offer of encouragement.

201. “Don’t U Know,” Paid in Full Soundtrack (2002): This originated as a Nas diss before it hit the public — according to Just Blaze, Jay adapted it into a more general single for the streets. The final draft retained some subliminal shots, but ultimately sounds like Hov is shadowboxing with himself. Jay’s punch lines and puns show he’s as light on his feet as ever.

200. “Do U Wanna Ride,” Kingdom Come (2006): An open letter — or, as it’s depicted here, a collect call — to Jay-Z’s then-incarcerated friend Emory Jones, looking back on their poor upbringings and painting an image of the riches and good life that awaits once he’s released.

199. “Green Light,” The Best of Both Worlds (2002): R. Kelly sing-raps a warning to naysayers and fellow R&B crooners over a gnarly electric guitar. Beanie Sigel and Jay-Z lend their support by splitting a verse.

198. “MaNyfaCedGod,” 4:44 (2017): If 4:44’s climax is its title track, in which Jay reveals and apologizes for his marital wrongdoings, then this two-part song is the resolution. On it, Hov discusses the healing and reconciliation process, candidly remembering the ways the turbulence in his marriage played out in the public (“Look at all we been through since last August / Skating through the rumors like, ‘Aw, shit!’”). He’s not as somber as he sounds on “4:44” — at times he’s even playful and a little cerebral — but Jay conveys the difficulty of continuing a relationship after someone majorly messes up.

197. “A Ballad for the Fallen Soldier,” The Blueprint²: The Gift & the Curse (2002): For the first half of his career, Jay-Z didn’t get enough credit for the conscious content implanted in his rhymes. This is one of his more overt examples — over a dreary piano backdrop, he compares the plight of soldiers to that of street hustlers. It’s not the most novel analogy, but this post-9/11 metaphor is especially resonant: “Bin Laden been happenin’ in Manhattan / Crack was anthrax back then, back when / Police was Al-Qaeda to black men.”

196. “Spiritual,” Tidal (2016): The unfortunate reality about this plea for an end to police brutality is that it was recorded years before it hit the public, yet felt timely when it finally dropped as a response to the murders of Philando Castile and Alton Sterling. “I am not poison / Just a boy from the hood that / Got my hands in the air / In despair don’t shoot,” he rhymes.

195. “What We Talkin’ About,” The Blueprint 3 (2009): Jay clears the air to open his 11th solo studio album, shrugging off insignificant chatter over futuristic keys.

194. “Crown,” Magna Carta … Holy Grail (2013): It’s crazy to think that Jay-Z went from ducking police and clashing with enemies in the streets to participating in hip-hop battles that seemed ready to erupt into real-life violence to songs like this Travis Scott–assisted affair, in which he taunts a corporate rival: professional sports agent Scott Boras.

193. “The Streets,” The Best of Both Worlds (2002): If anyone out there has a doctored, R. Kelly–free version of Best of Both Worlds, please tweet it to me @youngJFK. Thx!

192. “Crew Love,” Belly: Original Motion Picture Soundtrack (1998): Jay-Z is relegated to hook duty here, supervising Roc underclassmen Memphis Bleek and the newly signed Beanie Sigel, who packs his verse with a bevy of clever Monopoly references.

191. “Face Off,” In My Lifetime, Vol. 1 (1997): Jay-Z’s lyrics about love have evolved since releasing this hump-and-dump anthem with Sauce Money. They’re a formidable tag team no matter the subject matter, and the fun they’re having here is palpable.

190. “Minority Report,” Kingdom Come (2006): A sullen, time-capsule take on the socioeconomic injustice of the U.S. government’s piss-poor Hurricane Katrina relief efforts. Jay’s words make the song cry and Dr. Dre’s piano keys sound like teardrops.

189. “Snoopy Track,” Vol. 3 … Life and Times of S. Carter (1999): Jay-Z’s fourth studio album continued hip-hop’s growing shift away from regionalism. He’d already shown love to burgeoning New Orleans star Juvenile by blessing his breakout single, “Ha,” with a complementary remix verse the previous year. Juvie returns the favor here, sing-rapping a gruff hook over Timbaland’s revved-up instrumental, while Jay’s tempered flow panders to Dirty South listeners, insisting, “It’s for the black culture.”

188. “There’s Been a Murder,” Vol. 3 … Life and Times of S. Carter (1999): Jay-Z brings you back to the days before he was a world-known star, recalling shoot-outs and high-speed cop chases, and summing up his plight with this simile-metaphor hybrid: “See my life is like a seesaw/ And until I move this weight it’s gon’ keep me to the floor.” It’s a morose three-and-a-half minutes that sink an often upbeat LP.

187. “Only a Customer,” Streets Is Watching Soundtrack (1998): This song is built around an unexciting Mary J. Blige sample. But Jay’s lyrics are sharp as he contemplates whether the need for the finer things in life is worth the risks attached to selling weight.

186. “Anything,” The Truth (2000): Jay hijacks a bonus slot on Beanie’s debut to house this heartfelt dedication to his mom, nephews, and musical and business partners. But it’s docked for it’s Oliver! sample, a formula jacked from “Hard Knock Life” that didn’t pay dividends the second time around.

185. “30 Something,” Kingdom Come (2006): This was an awkward stage in Jay’s career. He boasts about his maturity, which entails everything from smoking Cuban cigars to maintaining an excellent credit score. Congrats? It’s elitist, but still, Jay’s lyrical interplay with Dr. Dre’s simple piano riff works.

184. “Somewhere in America,” Magna Carta … Holy Grail (2013): A rumination on cultural and socioeconomic politics — basically, the tanning of America — over a funky horn loop.

183. “Break Up to Make Up,” The Best of Both Worlds (2001): Why angry, intense sex is the best: a special report by R.
Kelly and Jay-Z.

182. “Legacy,” 4:44 (2017): Breezy horns add a sweet, mellow ambience to a track about maximizing generational wealth and erasing inherited family traumas.

181. “Party Life,” American Gangster (2007): This song sounds nothing like its title suggests. Hov spits some fly-ass talk about his couture, superstar wife, and overall cool-guy quintessence, as he’s been known to do so effortlessly.

180. “Honey,” The Best of Both Worlds (2002): Knowing R. Kelly’s real-life vices really reframes these collaborative projects, even making once-gleaming standouts like this one unlistenable.

179. “100$ Bill,” The Great Gatsby: Music From Baz Luhrmann’s Film (2013): Over a frenetic E*Vax beat, Hov points out the hypocrisy behind man’s relationship with the almighty dollar. Unsurprisingly, there’s coke talk too. It’s a wonder that Jay is still finding new ways to rap about moving weight, playing on everyone from Albert Einstein to Marvin Gaye to Taylor Swift to metaphorically describe his past life.

178. “8 Miles and Running,” 8 Mile: Music From and Inspired by the Motion Picture (2002): Jay throws his success in the faces of those who doubted he’d find a fruitful career in music.

177. “Stop,” Blueprint 2.1 (2003): Making hits seemed so easy for Hov around this time. This one might be forgotten among the surplus of turn-up tracks if it weren’t still a mainstay in the throwback portion of New York City DJs’ party playlists.

176. “Oh My God,” Kingdom Come (2006): A high-energy Just Blaze banger that feels like it’s seeking the combustible high of “Public Service Announcement (Interlude)” — there’s that same buildup to hard drums and guitar stabs. On the track, Jay skims through his life story, from growing up without a father to sonning his rap competition.

175. “Jigga That Nigga,” The Blueprint (2001): A rare but necessary deviation from the soul samples that shaped Jay-Z’s second classic LP. Poke and Tone cue up a catchy synth-based beat perfect for Jigga’s flossy rhymes (sample: “I am, killing ’em out there, they needing first aid / Cause the boy got more 6s than first grade”).

174. “That’s My Bitch,” Watch the Throne (2011):

The Throne’s version of romance: Kanye lays claim to his ex-girlfriend Amber Rose, while Jay-Z offers Beyoncé the ultimate compliment, insisting that her beauty belongs on the walls of museums (and simultaneously advocating for brown women to be exalted just as their white counterparts are already). The two rappers, with their different yet harmonious approaches, conquer a bubbly curveball of a beat by Q-Tip.

173. “Who Gon Stop Me,” Watch the Throne (2011): Jay completely obliterates this erratic Flux Pavilion sample, sounding not at all amazed when recalling how he ascended from the dirt to rolling in dough.

172. “Ride or Die,” Vol. 2 … Hard Knock Life (1998): Without saying his name, Jay snapped back at Mase here, addressing some of the Harlem rapper slash pastor’s disrespectful talk on 112’s “Love Me.” It’s an early indication of Hov’s battling ferocity, along with a glowing self-endorsement: “S. Carter, ghostwriter / And for the right price, I can even make yo‘ shit tighter.”

171. “Celebration,” Streets Is Watching Soundtrack (1998): The opening lines of Jigga’s blistering diss “Takeover” originated on this Roc-A-Fella 1.0 posse cut. He, along with Memphis Bleek, Sauce Money, and Wais P of Da Ranjahz, does this Commodores track of the same name proud.

170. “Open Letter,” Magna Carta … Holy Grail (2013): Jay-Z almost got Obama in trouble with this loosie that addresses his trip to Cuba with Beyoncé to celebrate their wedding anniversary (before travel restrictions were lifted). Jay gloriously trolled Republicans: “Boy from the hood but got White House clearance,” causing former press secretary Jay Carney to hold a press conference denying that the former president had communicated with Hov about his travel arrangements.

169. “Gangsta Shit,” The Professional (1998): Before the stick-up anthem that put 50 Cent on the map, Jay-Z dropped this graphic track alongside Ja Rule teaching you how to rob.

168. “Show You How,” The Blueprint²: The Gift & the Curse (2002): A seminar for the swaggerless on how to live your life like Shawn Carter, over a warped Just Blaze instrumental.

167. “Dope Man,” Vol. 3 … Life and Times of S. Carter (1999): Ironically, Jay ended up in trouble with the law around the time of the release of this extended metaphor comparing his musical rise to a high-profile criminal trial. He’d stabbed producer and executive Lance “Un” Rivera at New York City’s Kit Kat Club — reportedly over his alleged bootlegging of Vol. 3 — and was soon facing 15 years in prison if convicted. But life didn’t completely imitate art. Unlike his dramatic victory in “Dope Man,” Jigga copped a plea deal for three years of probation.

166. “Can I Live II,” Reasonable Doubt (1996): Despite being a forced continuation of the legendary original, Jay and Bleek get some solid lines off, so we’ll let them live.

165. “If I Should Die,” Vol. 2 … Hard Knock Life (1998): An optimistic look at life and death over a beat by Swizz that shifts away from the delightfully simple chord patterns that defined his early productions.

164. “Girls, Girls, Girls (Part 2),” The Blueprint (2001): Kanye picked the perfect Persuaders sample to bless this glorified remix that’s smoother than its more popular original. Jay nods to classic Lil Kim and Biggie lines while describing his ideal woman — “pretty, witty, girly, worldly” — criteria that still grace Instagram bios to this day.

163. “Come and Get Me,” Vol. 3 … Life and Times of S. Carter (1999): The one-minute intro to this song shines brightest, as Jay makes clear just how comfortable he is with handling and using his gun. Timbaland’s hard, bouncy beat regrettably switches up into something a bit smoother; still, Jay invites all challengers eyeing his crown, insisting they’d have to take it in blood.

162. “People’s Court,” Backstage: A Hard Knock Life (2000): The most clever of Jay’s songs based on the judiciary system, “People’s Court” flips courtroom terminology in a primer on street justice (“Save your opening arguments, hope you understanding / Two guns, right over left, that’s how I crossexamine”). The song samples the theme music from its titular TV series, but Jay neglects to name-drop another Brooklyn-born hardass: the Honorable Judge Judy.

161. “Some People Hate,” The Blueprint²: The Gift & the Curse (2002): Known for quoting Biggie throughout his career, Jay borrows lyrics from Tupac Shakur on this one, as he lashes back at those who’ve resented his success. Kanye West’s sped sample adds some sunniness.

160. “Oceans,” Magna Carta … Holy Grail (2013): This song’s concept is interesting enough — Jay juxtaposes the Trans-Atlantic Slave Trade and indentured servitude with the life of luxuriousness that he’s living in the 21st century. The radical thoughts and ideas here can sound disjointed at times, like a concept that’s not fully fleshed out.

159. “Beach Chair,” Kingdom Come (2006): This deep musing set to Chris Martin’s spacey instrumental is the most experimental track in Jay-Z’s catalogue. Penned in part as a letter to his unborn daughter, “Beach Chair” is a meditation on happiness, karma, and life’s purpose.

158. “Family Feud,” 4:44 (2017): Jay-Z has done his share of old-man cane shaking at hip-hop’s younger generation in the second half of his career, but here he comes to a place of acceptance, calling for unity among hip-hop artists, and, more generally, black people. Beyoncé’s background vocals shine through as well.

157. “Sweet,” American Gangster (2007): There’s a cycle that can permeate impoverished communities — one that finds a younger generation following in the footsteps of older figures who go illegal to live regal. Jay examines that repetition, mulling over the influence of his own criminal activities on the nephews who look up to him.

156. “The Bounce,” The Blueprint²: The Gift & the Curse (2002): Kanye West doesn’t squander his first full verse alongside his rap idol. Timbaland provides a funky instrumental that beats at your eardrums, and Kanye takes full advantage, warping in and out of character, stretching his voice and flow with a rubber band’s elasticity, and staking claim to past beat-making contributions to hip-hop history [“Izzo (H.O.V.A.),” “Takeover”].

155. “The Ruler’s Back,” The Blueprint (2001): A proper homage that re-creates Slick Rick’s 1988 song of the same name over a new set of trumpets, setting a celebratory tone for The Blueprint; it’s like a premature victory lap.

154. “FuckWithMeYouKnowIGotIt,” Magna Carta … Holy Grail (2013): Jay-Z reportedly lifted his verse from a shelved Watch the Throne track called “Living So Italian” for this luxury rap meets trap knocker that’s likely to blow out your AirPods.

153. “Illest Motherfucker Alive,” Watch the Throne (2011): In case you can’t tell by this song’s title, modesty is not the Throne’s strong suit. “Basquiats, Warhols serving as my muses / My house like a museum so I see ’em when I’m peeing,” Jay rhymes, humble as ever, over a deep cello and sparkling keys.

152. “Stick 2 the Script,” The Dynasty: Roc La Familia (2000): This tough-talking duet between Beanie Sigel and Jay-Z feels redundant on The Dynasty — the similar but stronger “Streets Is Talking” appears three tracks earlier — but it’s still dope.

151. “Already Home,” The Blueprint 3 (2009): In one of Jay’s strongest rap performances on The Blueprint 3, he explains, in an impressive variety of ways, how he’s several levels above any other living rapper.

150. “The Watcher 2,” The Blueprint²: The Gift & the Curse (2002): Jay really likes sequels. This one finds him in the driver’s seat, inviting Rakim and Dr. Dre, who recorded the original track, along for the ride. Perhaps the rehash was a passive-aggressive play by Hov, though — Nas is rumored to have written Dre’s 1999 prequel.

149. “Picasso Baby,” Magna Carta … Holy Grail (2013): Probably the best product of Jay-Z’s art-collecting obsession. The electric guitar-powered beat during the second half would sound at home on Vol. 1, in the best way.

148. “Poppin’ Tags,” The Blueprint²: The Gift & the Curse (2002): You might’ve felt short-changed when this long-awaited Hova and OutKast collaboration finally happened — and André 3000 was absent. But Twista and Killer Mike join Jay and Big Boi for a knocking ode to shopping sprees over a brilliantly chopped Marvelettes sample, courtesy of the Louis Vuitton Don himself, Kanye West.

147. “I Know,” American Gangster (2007): Leave it to Jay-Z and Pharrell to record a song about heroin and the destructiveness of addiction, and turn it into an entirely different kind of hit.

146.“Rap Game / Crack Game,” In My Lifetime, Vol. 1 (1997): Hov puts up the split screen once again, drawing parallels between the two vocations he knows best. Turns out, they’re not all that different.

145. “Blue Magic,” American Gangster (2007): Rakim guests here, too, albeit only in spirit. Over a minimalist Neptunes beat, Jay pays homage to Rakim Allah with several references to the hip-hop legend’s song “My Melody.”

144. “Hovi Baby,” The Blueprint²: The Gift & the Curse (2002): Jay-Z took a month-long vacation in the South of France between the 2002 releases of The Best of Both Worlds and The Blueprint². He returned home to a mess. Roc-A-Fella co-founder Damon Dash made a bunch of personnel changes at the label without Jay’s consent — most notably, promoting Beanie Sigel and Cam’ron to vice-presidents, a point of contention that placed a wedge between the former partners. Also, Nas had tried to lynch an effigy of his former rival at Summer Jam before being blocked by Hot 97. One of Jay’s first orders of business after coming home was to visit Funkmaster Flex at the radio station and drop a ceremonial freestyle on the airwaves, previewing the second verse of this song. He keeps that same rejuvenated timbre on “Hovi Baby,” also injecting the sternness of an annoyed king displeased with the state of his kingdom and threatening to go full tyrant. “In my absence / cats get / absent-minded,” he rhymes, dropping the gavel over a Just Blaze instrumental that sounds like it belongs on an ’80s TV game show.

143. “The Best of Both Worlds,” The Best of Both Worlds (2002): This song’s title rings true as Jay and Kellz trade the mic back-and-forth, ringing in their first duet album. R. Kelly’s singing is over-the-top at times, but it works.

142. “Guilty Until Proven Innocent,” The Dynasty: Roc La Familia (2000): Jay raps about the injustice of being a celebrity undergoing a criminal trial — his felony assault charges for stabbing Lance Rivera were still outstanding — and invited R. Kelly, of all people, to sing about innocence.

141. “Caught Their Eyes,” 4:44 (2017): Jay acknowledges how the same intuition that’s kept him one step ahead of peril in the streets now helps him navigate the corporate world, in the process ripping into the head of Prince’s estate, taking to a peppy No ID beat to address some Tidal beef.

140. “Squeeze 1st,” The Dynasty: Roc La Familia (2000): Jay’s flow is super loose over this Rick Rock loop, which sounds like it’s straight out of a video game from the ’90s. He goes at it for less than four minutes, but I could listen to Hov spit over this beat for hours.

139. “A Week Ago,” Vol. 2 … Hard Knock Life (1998): Jay-Z is a master at humanizing tales from the hood. Here, he opens up about a close friend and fellow hustler who snitched once he got snagged by police. Jay’s delivery when rapping about his turncoat friend — reportedly estranged homie DeHaven Irby — is cold, but you get the feeling he’s hurt by the betrayal. “When he called collect and I heard his name / I quickly accepted, but when I reached the phone / He’s talking reckless, I can sense deceit in his tone,” he rhymes. It’s a needed personal touch on an album stacked to the brim with hits.

138. “American Dreamin,’” American Gangster (2007): This song sounds just as dreamy as its title suggests, with its delightful Marvin Gaye sample. Jay is a ghetto griot here, sharing a story about how a group of tenacious kids with big aspirations and limited options find themselves in the coke game.

137. “Watch Me,” Vol. 3 … Life and Times of S. Carter (1999): There’s an endearing carpe diem outlook here, although present-day Jay-Z probably cringes listening back on sterling financial advice like “Save for what? Ball till your days is up.”

136. “It’s Alright,” Vol. 2 … Hard Knock Life/Streets Is Watching Soundtrack (1998): Some posturing from Memphis Bleek and an on-the-verge Jay-Z that’s amplified by cool whirring sounds lifted from Kraftwerk’s “The Hall of Mirrors.”

135. “Primetime,” Watch the Throne (2011): A gratuitous Watch the Throne bonus track that showcases a complex numerically themed verse from Jay alongside the usual improper humor from Yeezy over No I.D.’s shimmery piano.

134. “Soon You’ll Understand,” The Dynasty: Roc La Familia (2000): This feels like a first draft of “Song Cry,” particularly this track’s middle verse, which wrestles with themes of love, loyalty, and maturity. It’s one of three fictionalized scenarios that Jay delivers with believable emotion over a haunting instrumental; the common thread is a plea for empathy.

133. “Adnis,” 4:44 (2017): Like a page out of Jay-Z’s diary — or an exercise assigned by his therapist — this open letter asks his late father questions that have no answers, over a piano melody that seems to trip over itself. “Must’ve been some pain in your past, too / Must’ve been a karma that was past due,” he rhymes. The song ends in a place of peace, acceptance, and forgiveness.

132. “NYMP,” Vol. 3 … Life and Times of S. Carter (1999): A knocking dedication to Marcy Projects that plays like a lite sequel to “Where I’m From.”

131. “Parking Lot Pimpin,’” The Dynasty: Roc La Familia (2000): Why waste time within the confines of a crowded club when you can create your own scene in the parking lot? Jay, Beans, and Bleek indulge their love for hot wheels over a thumping beat, saluting the road warriors and auto aficionados who know the real party goes down at the let out.

130. “Pray,” American Gangster (2007): This introduction to American Gangster plays on the parallels between Jay-Z’s hustler past and the Denzel Washington–starring film of the same name (itself based on the life of Harlem drug kingpin Frank Lucas). Close your eyes and listen to Jay’s narrative; it’s like a movie in itself.

129. “Real As It Gets,” The Blueprint 3 (2009): This triumphant record was originally intended for Young Jeezy’s TM:103 Hustlerz Ambition before Hov snagged it for his own project. It’s a nice score, a bright spot on an uneven third Blueprint album.

128. “Streets Is Talking,” The Dynasty: Roc La Familia (2000): Aside from maybe Sauce Money, no one brings grittier street reportage out of Jay-Z than Beanie Sigel. What could’ve been an underwhelming update to “Streets Is Watching” shines as Sigel raps right up until the beat ends, closing with an aggressive a cappella.

127. “Say Hello,” American Gangster (2007): Jay plays the villain role here, taking a defensive tone as he justifies the criminal route he chose while evoking the moments just before Tony Montana (Scarface) and Frank Lucas (American Gangster) began their respective falls from drug-lord glory. DJ Toomp provides a stirring, cinematic backdrop — these two really should work together again.

126. “Welcome to the Jungle,” Watch the Throne (2011): Kanye allows Jay to take the lead here, rapping from his therapist’s couch about loss and depression — a surprising turn on an album that’s often preoccupied with excess and grandiosity.

125. “I Got the Keys,” Major Key (2016): On paper, Jay-Z and Future make for curious collaborators. But music matchmaker DJ Khaled paired them up proper, allowing Hendrix to lay down an inescapable hook and Hov to spit cloth talk of only the highest thread count.

124. “No Hook,” American Gangster (2007): The-Dream made it a hot line; Jay made it a hot song. Hov lifts a memorable lyric from “Shawty Is Da Shit” to tie together three tough verses of his own.

123. “Gotta Have It,” Watch the Throne (2011): Even more impressive than Jay rapping about planking on a million dollars or the palpable chemistry he shares with Kanye on the mic is that ’Ye and Pharrell chop up three (!) different James Brown samples and lay them down over a mesmerizing loop for one of Watch the Throne’s most enjoyable tracks.

122. “Thank You,” The Blueprint 3 (2009): This song closes with an extended metaphor about rappers whose album sales are not up to snuff; despite needlessly evoking 9/11 imagery, it’s wonderful.

121. “Success,” American Gangster (2007): Nas and Jay-Z have yet to deliver a truly classic duet, but this No I.D.–produced heater comes damn close. Over a crescendoing organ riff, the two rap legends grumble about the misfortunes that come along with being filthy rich. Nas sneaks in a subliminal potshot about his newfound friendship and business alliance with his former archnemesis (he signed to the Jay-Z-led Def Jam Records in 2006): “Worst enemies wanna be my best friends / Best friends wanna be enemies like that’s what’s in / But I don’t give a fuck, walk inside the lion’s den / Take everybody’s chips, about to cash them in.”

120. “So Ambitious,The Blueprint 3 (2009): The Neptunes and Jay-Z make magic more often than not. These horn flourishes and xylophone taps are the perfect sound-bed for a retelling of how a kid from Marcy Projects massively succeeded against all odds.

119. “People Talkin’,” Jay-Z: Unplugged (2002): Ski’s pounding boom-bap and Jay-Z’s endless lyrical warning shots make the perfect marriage for this bonus track that really belongs on a proper studio release.

118. “Hola Hovito,” The Blueprint (2001): An upbeat Timbaland-produced banger that tempers The Blueprint’s heavy soul offerings and panders to Latino listeners without completely butchering the Spanish language.

117. “Somebody’s Girl,” The Best of Both Worlds (2002): Jay-Z may have been the original Mr. Steal Your Girl — this catchy track from his ill-fated duet LP with R. Kelly is all about the art of being “the other guy.” The song is savage, bumped up five notches for the heavy allusions to Martin Lawrence’s classic stand-up comedy film You So Crazy in verse three.

116. “Smile,” 4:44 (2017): This track is immediately important for its powerful revelation that Jay-Z’s mother identifies as a lesbian. But what’s most impressive is the extended closing verse, in which Jay runs down the many ways he’s prevailed in various industries simply by being his own boss.

115. “Jay-Z Blue,” Magna Carta … Holy Grail (2013): Before the fateful elevator ride gone viral, Jay gave a peek at the cracks forming in his family life. It’s the most candid four minutes on the album — Jay goes through a range of emotions, from wanting more time with his wife and daughter to needing a three-week vacation from it all to wondering if his own dad’s bad (or absent) parenting is hereditary. Jay is nervous, unsure, maybe even neurotic — a type of vulnerability previously unseen, a tip of the transparency iceberg that was to come.

114. “American Gangster,” American Gangster (2007): Producers Sean C & LV, along with Diddy, steered the majority of the music on American Gangster, creating a moody atmosphere for Jay to deliver his Frank Lucas–inspired storyline. The sonic parameters are appropriate, but on this bonus cut — over Just Blaze’s sunny Curtis Mayfield sample from the same era — Jay sounds like an emcee unleashed, rapping with more energy than anywhere else on the entire project.

113. “Some How Some Way,” The Blueprint²: The Gift & the Curse (2002): Putting Beanie Sigel, Jay-Z, and Scarface on the same track had already proved to be a promising formula after the release of “This Can’t Be Life” and “Guess Who’s Back.” They keep the winning streak going with this mellifluous retrospective about escaping poverty.

112. “Breathe Easy (Lyrical Exercise),” The Blueprint (2001): A bout of wordplay aerobics using workout terms; will help get you through leg day.

111. “Heaven,” Magna Carta … Holy Grail (2013): Hov questions religion in a truly curious way, examining the morality and validity of denominational teachings. It’s a tension he’s played with throughout his career; here he evokes religious symbolism with lines like, “Y’all dwell on devil shit, I’m in a Diablo,” and “Fresh in my Easter clothes feeling like Jesus.”

110. “From Marcy to Hollywood,” The Players Club Soundtrack (1998): Sauce Money, Memphis Bleek, and Jay-Z are three the hard way. The Marcy lyricists narrate scenarios that prove in the streets, wolves can take on many different forms.

109. “What the Game Made Me,” I Got the Hook-Up Soundtrack (1998): Three the hard way come harder over twinkling chimes, although Bleek shines brightest this time.

108. “Who You Wit”/“Who You Wit II,” In My Lifetime, Vol. 1 (1997): This is just a bunch of slick pimp talk over Ski’s jazzy piano and guitar sample. The opening gambit — “I love bitches, thug bitches, shy bitches / Rough bitches, don’t matter you my bitches” — recalls Ice-T’s “99 Problems,” which Jay would later recreate in 2003.

107. “Ignorant Shit,” American Gangster (2007): Just Blaze whips up a timeless Isley Brothers track for Jay to clap back at hip-hop detractors and mock listeners who find his thoughtful songs too sophisticated. Most memorable, though, is his confirmation that most rappers are faker than a $4 bill, not unlike WWE wrestlers: “Don’t fear no rappers / They’re all weirdos, De Niros in practice.” Then, with a wink, Jay includes himself in the assessment. “Actually, believe half of what you see / None of what you hear, even if it’s spat by me / And with that said, I will kill niggas dead.” The 2005 leak of this song is the best version, though, adding an alternate closing verse from Jay in place of Beanie Sigel.

106. “Diamond Is Forever,” The Blueprint²: The Gift & the Curse (2002): The type of chant-along Roc-A-Fella anthem that’s perfect for throwing your diamond in the sky if you feel the vibe.

105. “Shining,” Grateful (2017): This song marked Jay-Z and Beyoncé’s first collaboration since 2013’s “Drunk in Love.” On this joyous, up-tempo DJ Khaled cut, they toast to their extensive winning streaks, offering not even the slightest hint of the sobering 4:44 that would follow months later.

104. “Money Ain’t a Thang,” Vol. 2 … Hard Knock Life (1998): This is a soundtrack for bad financial decisions, and the aspirational hit single with Jermaine Dupri that set the stage for Jay-Z’s impending hip-hop takeover. To think, at the time of this song’s release Jay was probably pulling somewhere in the ballpark of one percent of his estimated 2017 $810 million net worth (that is, $8.1 million).

103. “Fallin’” American Gangster (2007): Jay evokes the misery of a crumbling criminal empire — the typical tale of a hustler who doesn’t know when to stop pushing his luck — over a melancholy piano-based melody by JD.

102. “The Joy,” Watch the Throne (2011): Jay and Kanye, as usual, take different approaches over this peak nostalgia Pete Rock track (somehow, it’s the legendary producer’s first collaboration with Hov). While Kanye rotates women and extols the merits of birth-control pills, Jay gives all glory to Gloria Carter, his mom.

101. “Blueprint 2,” The Blueprint²: The Gift & the Curse (2002): An overlooked attack in Jay’s battle with Nas. There are some effective blows here (he calls Nas’s brother, Jungle, a “garden”), but Hov gets docked for the dated and silly Austin Powers references in the hook.

100. “Show Me What You Got,” Kingdom Come (2006): A fun, youthful introduction to the maturity and grown-folks business that comprises much of Kingdom Come.

99. “Bam,” 4:44 (2017): With Brooklyn’s dense West Indian demographic, it’s shocking how seldom Jay-Z has collided with reggae artists or hopped on dancehall-inspired riddims. Sure, Sean Paul appeared on The Blueprint² and yeah, he tacked a verse onto the remix of Mavado’s “On the Rock” in 2008, but this majestic Damian Marley duet — with nods to Sister Nancy and Inner Circle classics — is as Kingston as you’ll find on this list. It’s a welcome voyage.

98. “Kingdom Come,” Kingdom Come (2006): Back when hip-hop’s King of New York crown still meant something, Hov returned from his pseudo-retirement to lock it down once again. Just Blaze scrambled up a ridiculous sample of Rick James’s “Super Freak” for Shawn Carter to announce his return — and namedrop a bunch of comic-book heroes in the process.

97. “Meet the Parents,” The Blueprint²: The Gift & the Curse (2002): This piano-sprinkled allegory is often presented as evidence of Jay-Z’s storytelling ability — I’m partial to his “Coming of Age” and “Friend or Foe” dilogies instead. It’s not that “Meet the Parents” isn’t a quality tale; there’s solid use of apprehension, plot twist, imagery, and irony. But the track is heavy-handed in its execution, an approach that Jay reveals was intentional in his book, Decoded. “It was a morality play,” says Jay, “a PSA for that generation of men who may as well have emptied their guns on their sons when they left their lives.”

96. “Blueprint (Momma Loves Me),” The Blueprint (2001): What separates Jay-Z from other lyrically gifted, hit-making emcees — like, say, Fabolous — is his willingness to go in-depth about his struggles and successes. In this autobiographical track, he reels off names of loved ones who’ve shaped his life in ways small (“Annie shampooed my hair”) and big (“Jaz made me believe this shit was real”). It all helps to nurture the connection between the artist and listener, a closeness that’s only grown as Jay’s career has progressed.

95. “December 4th,” The Black Album (2003): With help from his mom, Jay-Z sums up his pre-stardom life in three verses. It’s a captivating audio memoir set to a stirring Just Blaze beat.

94. “Change the Game,” The Dynasty: Roc La Familia (2000): By the time Dynasty dropped, the Roc’s core was solid: Beanie Sigel brought imposing wordplay with finesse, Memphis Bleek was all energy and agility, and Jay moved like the boss, with a cool delivery and top-notch lyricism. The trio brings exactly that over this bouncy Rick Rock production — the best example of their gratifying synergy.

93. “Dear Summer,” 534 (2005): Reasonable Doubt was supposed to be Jay-Z’s first and only album. But as his storied career proves, he could never definitively say good-bye to music. He attempted to on this track, addressing a farewell letter to the summer months that he’d once regularly dominated. Something about these sped-up piano keys, lifted from Weldon Irvine’s “Morning Sunrise,” suggest sincerity, but this ended up being more of a “see ya later.”

92. “Marcy Me,” 4:44 (2017): You might have to rewind Jay’s agile flow — easily 4:44’s most nimble display — to catch all of the puns, but it’s worth it to witness this dazzling lyrical performance in all of its glory.

91. “Girls, Girls, Girls,” The Blueprint (2001):

Jay-Z preys on cultural stereotypes to describe his many women and — perhaps most shamefully — reveals himself to be a viewer of sophomoric comedy flick Deuce Bigalow. Still, the chipmunked Tom Brock sample is undeniable.

90. “Kill Jay Z,” 4:44 (2017): This isn’t the first time Jay-Z has killed himself, or rather his likeness, via his art. He depicts his assassination in the video for “99 Problems,” and repeats “Jay-Z is dead” in “There’s Been a Murder.” But this song is different. Jay singles out his ego, separating himself from the persona that led him to shoot his own brother as a young teen, or cheat on his wife. It’s an interesting lens through which to observe the indiscretions he details on 4:44 — he’s taking accountability while simultaneously distancing himself for his most shameful actions, emerging on the other side a new and better man.

89. “The Story of O.J.4:44 (2017): A prudent look at the role of the black elite — underlined by the sample of Nina Simone’s racially significant “Four Women” — that uses disgraced former football legend O.J. Simpson as a worst-case scenario. Jay pays it forward, urging listeners to strive for investment, ownership, and wealth that can be passed down to descendants.

88. “The Prelude,” Kingdom Come (2006): When this number opened Jay-Z’s big “comeback” album, it seemed like Marcy’s begotten son might’ve had another classic album on deck. It turned out that couldn’t have been further from the truth. But producer B-Money helped make a solid first impression by hooking up an alluring clarinet melody that could charm a cobra. Hov slithers about, lamenting the plummeting stock of rap lyricism. It’s a memorable album intro, Hov’s own State of the Union address.

87. “03 Bonnie & Clyde,” The Blueprint²: The Gift & the Curse (2002):

Jay remakes Tupac Shakur’s “Me and My Girlfriend” — all about his relationship with a gun — in the most literal way possible: by converting it into a duet with his real-life then-girlfriend, Beyoncé. Still, with its romantic guitar and cutesy inside jokes (“Only time we don’t speak is during Sex and the City”), the song was the perfect way to capitalize on the rumor mill churning about Jayoncé with their undeniable first collaboration.

86. “Intro/A Million and One Questions/Rhyme No More,” In My Lifetime, Vol. 1 (1997): Two thumping beats by DJ Premier plus two stellar verses by Jay-Z equals one impressive sophomore-album opening statement that puts an iconic Aaliyah sample to good use.

85. “Why I Love You,” Watch the Throne (2011): Kanye and Jay seem genuinely hurt when discussing former friends — particularly beneficiaries of their influence — who’ve switched sides. “Wasn’t I a good king?” Jay asks. “Maybe too much of a good thing, huh?” ’Ye answers. Mr. Hudson redeems himself for “Young Forever” with a fitting vocal on the hook.

84. “Hey Papi,” The Klumps Soundtrack (2000): Timbaland and Jay were at their creative peak at the turn of the century. Over a zany, overloaded instrumental, Hov opens up to the idea of a romantic relationship that doesn’t end 15 minutes after intercourse.
Amil’s unique voice add a minor, but winning touch.

83. “Never Change,” The Blueprint (2001): The life of a drug dealer can sound glamorous — that is, until you misplace or otherwise fuck up 92 kilos of cocaine. Over Kanye’s genius David Ruffin vocal chop, Jay recalls how he “crawled back” from a major L in less than one workweek. Is he full of shit? Who knows. Regardless, the anecdotal aside successfully builds the urban legend of Brooklyn’s most famous reformed pusher.

82. “All I Need,” The Blueprint (2001): Jay adds a light touch to the more serious back half of The Blueprint with a tour rider for his everyday life.

81. “It’s Like That,Vol. 2 … Hard Knock Life (1998): Jay seasons a gorgeously simple Kid Capri beat with clever lines like, “Impregnate the world when I come through your speakers.”

80. “Intro,” The Dynasty: Roc La Familia (2000): One of Jay’s most beloved album intros, bolstered by Just Blaze’s bedazzling instrumental. Every line here has purpose, introspection, and wit, as he drops layered rhymes about his money-focused mentality — and how swiftly his riches (and life) could be snatched away if he’s not cautious.

79. “Threat,” The Black Album (2003): It seems like Jay lists all 6 million ways to die (by his own hands) over 9th Wonder’s masterful chop of “A Woman’s Threat” by R. Kelly. This gets bumped up ten spots for Cedric the Entertainer’s comic relief.

78. “Cashmere Thoughts,” Reasonable Doubt (1996): This song started out as a joke. Jay had a pimp name and persona — Cashmere Jones — that he employs here, setting out to drop the slickest rhymes he could think of. Which explains ridiculous and ruthless lines like, “I pimp hard on a trick, look / Fuck if your leg broke, bitch, hop up on your good foot,” rapped over Clark Kent’s smooth production.

77. “Made in America,” Watch the Throne (2011): This song was originally titled “Sweet Baby Jesus,” but there’s a dual meaning at play in the official title that subtly accentuates Kanye and Jay’s intentions. The surface interpretation is “American-made,” as if to say the two rappers are products of all of the glory, hypocrisy, and injustice of the U.S. — the testimonies of their respective come-ups on this track are tied to that heritage. Alternatively, the title could imply that the two superstars are “made,” as in financially loaded, as an outcome of their groundwork. Either way, this is another masterful pairing with the great Frank Ocean.

76. “Glory (B.I.C.)” (2012): A heartwarming track celebrating Jay-Z and Beyoncé’s first child, Blue Ivy Carter, who was born just days before this song’s release. The Neptunes provide soothing synths and keys that are lullaby-ready, while Jay raps pure joy, reminiscent of Stevie Wonder’s dedication to his daughter on “Isn’t She Lovely.” Hov alludes to some heavy moments as well — a past miscarriage, and the deaths of his dad and singer-friend Aaliyah — but by the end of the runtime you’re left marveling about how adorable (and spoiled!) Blue Ivy is gonna be.

75. “In My Lifetime” (1995): A single from deep in the Shawn Carter catalog with shadows of his speedy flow, but mostly characterized by a poised delivery. His skill is undeniable here, as he raps about his need for money by any means, seemingly not yet 100 percent sold on rap as a full-time hustle.

74. “My 1st Song,” The Black Album (2003): Bye-bye Jigga, again. This Black Album adieu sounds like a tropical vacation, with dancing strings that Jay skips across in double-time. The spoken outro may or may not have inspired Kanye to rant at the end of The College Dropout.

73. “You, Me, Him, and Her,” The Dynasty: Roc La Familia (2000): This mesmerizing instrumental by producer Bink was easily one of that year’s most coveted, thanks in large part to the verses the varsity Roc lineup lays down. Bleek, Beanie, Jay, and Amil — who gets just a scant six bars, poor Amil — are at their most synergetic, combining like Power Rangers’ Megazord, or, better yet, a sturdy hip-hop crew.

72. “On to the Next One,” The Blueprint 3 (2009): Jay fancies himself a trendsetter over this otherworldly head-nodder of a Swizz beat, accomplishing here where “Off That” failed.

71. “I Can’t Get Wit Dat,” B-Side (1995): There’s something refreshing about the way that Jay-Z speed-raps through this single from his early rhyming days. Lyrically, it’s just a bunch of bragging about being a supreme emcee. But the way he puts his words together is so irresistible — at one point Jay mouths the sound of a money counter, hitting each syllable like a stone skipping across a lake.

70. “Coming of Age (Da Sequel),” Vol. 2 … Hard Knock Life (1998): A tale of a disgruntled hustler who’s hungry for a bigger cut of his OG’s earnings. The illest thing about this continuation from Reasonable Doubt’s symbolic origin story is that Jay-Z and Memphis Bleek stretch out a 30-second encounter into a four-minute song, with all of the tension of a muscle knot. The bulk of the action takes place in their minds, building up with suspense and ending in reality — a promising musical career for Bleek.

69. “Take You Home With Me a.k.a. Body,” The Best of Both Worlds (2002): In retrospect, I’m starting to believe that R. Kelly’s “home” is the original Sunken Place. Jay leads the way here, though, spitting the type of one-liners that might dominate your Twitter feed had this song dropped today. He discusses how a woman’s curves “make it hard to watch a flat TV,” exposes denims “that make objects bigger than they appear like a rear-view mirror,” and establishes the official wifey uniform: a powder-blue Rocawear velour suit and white Nikes. The beat, which sounds like a monophonic 8-bit ringtone, burrows its way into your brain — these days, it evokes the early-2000s perfectly.

68. “Brooklyn Go Hard,” Notorious (Music from and Inspired by the Original Motion Picture) (2009): There hasn’t been a prouder, more brash BK anthem in the nearly ten years since this song dropped. Jay’s opening patois could use some coaching, but his lyrical Ginsu is sharp — witness how he brilliantly deconstructs and reconfigures baseball legend Jackie Robinson’s name for his own indulgent purposes. Santigold’s sung hook and bridge are 24 karat.

67. “D.O.A. (Death of Auto-Tune),” The Blueprint 3 (2009): The futurist Blueprint 3 is all about progression, but here Jay-Z longs for the past: bygone days when, according to him, pitch-correction software didn’t compensate for lack of creativity in hip-hop. His moratorium was issued over an insane guitar-and-brass medley that was just begging to be sampled.

66. “It’s Hot (Some Like It Hot),” Vol. 3 … Life and Times of S. Carter (1999): Hov counters 50 Cent’s jab on “How to Rob” with a piercing dart on a song that lives up to its name: “I’m about a dollar, what the fuck is 50 Cent?” Touché.

65. “This Life Forever,” Black Gangster Soundtrack (1999): An underrated and overlooked jewel in Jay-Z’s discography.
With Über-witty punch lines and wordplay, he illustrates stark portraits of the projects, summing things up with a sobering conclusion: “Let’s face it / Either you’re dough chasing or basing.”

64. “1-900-Hustler,” The Dynasty: Roc La Familia (2000): Hov jacked this concept — a hotline phone service that provides nefarious advice for starry-eyed criminals — from Houston duo Convicts’ 1995 song “1-900-Dial-A-Crook,” which features Geto Boys. But this Roc classic is most significant for introducing the world to Freeway. His elevated vocal pitch is sui generis. The way he modulates between some syllables (“hus-tel-ers,” “cus-to-mers”) and elongates others (“F-R / Two E’s / That’ll be two G’s”) are like extensions of the beat. And Free’s street commandments are coded, succinct, and sound counsel that you should definitely not try at home — all the makings of a timeless first outing.

63. “La-La-La (Excuse Me Miss Again),” Blueprint 2.1 (2003): Rather than a remix, this is a complete reimagining of the genteel “Excuse Me Miss.” The Neptunes cook up some humming synths and soft bongos for Jay to stroke his own ego in rhyme.

62. “Reservoir Dogs,” Vol. 2 … Hard Knock Life (1998): When you’re rhyming in a cypher of this caliber, there’s zero room for a shaky flow or trash punch line. You’ll find neither on this high-stakes posse cut. Every verse here deserves a flame emoji — but leaving it at that is no fun. So here goes, verses ranked from best to least-best: Sauce Money, Styles P, Jay-Z, Jadakiss, Sheek Louch, Beanie Sigel.

61. “No Church in the Wild,” Watch the Throne (2011):

Propelled by an urgent bass line, Kanye and Jay-Z offer strikingly different musings on religion. Jay contemplates ancient Socratic philosophy, while Kanye praises polygamy, cocaine, and Red Bull. Frank Ocean ties it all together by singing a string of rhetorical questions, but sounds great nonetheless.

60. “Bring It On,” Reasonable Doubt (1996): Jay-Z envisioned Nas and AZ co-starring on this Reasonable Doubt deep cut, which, needless to say, could’ve been an NYC collaboration for the ages, right up there with his Biggie-featured “Brooklyn’s Finest” from the same album. Still, Sauce Money, Jaz-O, and Jigga all bring A-game bravado to DJ Premier’s sleepy violin and pummeling boom-bap.

59. “Heart of the City (Ain’t No Love),” The Blueprint (2001): A song about the big bull’s-eye that appears on your back once you’ve reached the top of your class. Whereas Jay is usually combative when discussing haters, he sounds incredulous here, wondering what he’s done to deserve such icy treatment. Thank god Kanye gave Hov this beat — built around a rousing Bobby “Blue” Bland sample — and not DMX, as ’Ye has said was the original plan.

58. “What More Can I Say,” The Black Album (2003): Jay hops on an exuberant instrumental to put forth an impassioned five-minute plea, both showing and telling why he’s hip-hop’s G.O.A.T. He does a convincing job.

57. “Imaginary Player,” In My Lifetime, Vol. 1 (1997): It’s astounding how relevant this song is two decades after its release, in an era when social media is a tool for many to favorably skew the degree of their life’s awesomeness. Back in ’97, Jay called folks out for faking it ’til they make it, with a dismissive tone, collected flow, and receipts for his own boasts.

56. “Excuse Me Miss,” The Blueprint²: The Gift & the Curse (2002): With “Excuse Me Miss,” Jay-Z made pursuing a woman sound easy. All you need are your own lucrative sneaker and liquor business deals, some housekeepers, and not one but two dishwashers and she’ll fall right into your arms. Hov combined The Neptunes’ airy synths with inspiration from Luther Vandross’s “Take You Out” to make a courtship soundtrack that convinced an entire hip-hop generation that most of us can’t keep big pimpin’ forever (even Jay). The song introduced a romantic opening phrase into the pop lexicon (then-teenager Chris Brown dropped his own “Yo (Excuse Me Miss)” three years later). The fact that this song is definitely probably a reenactment of how Jay wooed Beyoncé doesn’t hurt, either.

55. “Lucky Me,” In My Lifetime, Vol. 1 (1997): Jay lets his guard down for a moment to lament the trappings of celebrity: jealousy, envy, deceit. His awareness of how quickly a bad decision could derail his career — or inhibit his freedom — is acute, especially for an artist so new to the spotlight (who’d be threatened with heavy jail time for stabbing Lance Rivera two years later). It’s a vulnerable, insightful look inside the mind of a young Shawn Carter.

54. “44 Fours (Live From Radio City Music Hall)” (2006):

Jay doubled down on Reasonable Doubt’s number-based lyrical exercise “22 Two’s” — on which he raps phonetic variations of “two,” 22 times — for the album’s tenth anniversary. Here he tackles “four” (and “for,” etc.) 44 times, and while the track lacks the novelty and fully formed song execution of the original, Jay’s, um, four-play is just as proficient.

53. “Roc Boys (and the Winner Is …),” American Gangster (2007):

A jubilant anthem, perfect for toasting to advancement, comradery, or prosperity, and then getting wasted at the bar with friends.

52. “Is That Yo Bitch,” Vol. 3 … Life and Times of S. Carter (1999): It’s impossible to listen to this song without imagining it as a reference to Jay’s dalliance with Carmen Bryan, the mother of Nas’s first child. Especially considering Hov’s recount of his backseat encounters with Carmen on the below-the-belt diss “Super Ugly.” But subliminal or not, his shameless perspective on being a side dude thankfully produced this catchy gem that only existed on international releases of Vol. 3 before Memphis Bleek revamped it for his own sophomore album.

51. “In My Lifetime (Remix),” Streets Is Watching Soundtrack (1998): I’m breaking this list’s no-remix stipulation because of this song’s significance to the Jay-Z canon. Whereas the original is sonically rougher around the edges, this Jaz-O-helmed revamp, with its pretty chimes and Soul II Soul sample, feels musically polished. Jay tells a story of a young hustler’s rise to the top of the drug game — ironically, it feels like a foreshadowing of his future in music. “I found a new route, you ’bout to see my life change,” Jay rhymes. Boy, was he right.

50. “H*A*M,Watch the Throne (2011):

No one quite anticipated that the first release from Watch the Throne would be helmed by the newbie producer who had been creating trunk-rattlers for Rick Ross and Waka Flocka Flame. But indeed it was Lex Luger who served up luxuriance with an audacious, aggressive beat, bizarrely juxtaposed by a shrill opera segment (clearly Kanye’s idea). If the Throne set out to make a statement, well, mission accomplished.

49. “Lost One,” Kingdom Come (2006): A song about various types of loss that finds Jay-Z heartbroken as he dwells on the death of his nephew, Colleek. The 18-year-old was killed in a car accident while driving the Chrysler 300 that Jay bought him. But he finds solace in the fact that his nephew — who Jay has periodically rapped about over the course of his career — was expecting a child. “Even the greatest loss holds the possibility of redemption,” Jay wrote in Decoded. The same track finds Hov tackling his fallout with Damon Dash and addressing a seemingly failed relationship, supposedly with actress Rosario Dawson.

48. “So Ghetto,” Vol. 3 … Life and Times of S. Carter (1999): Fresh off of the quintuple-platinum success of his best-selling album, Vol. 2, Jay-Z insists that his newfound superstardom hadn’t gone to his head.
Everything about this track is unapologetically gutter, from a DJ Premier guitar sample that’s both grating and delicate, to Hov’s brash lyrics (The line “We tote guns to the Grammys, pop bottles on the White House lawn” very likely influenced Kendrick Lamar’s brazen To Pimp a Butterfly album cover, 15 years later.)

47. “Dirt Off Your Shoulder,” The Black Album (2003):

This is like Jay-Z’s play on OutKast’s “So Fresh, So Clean,” continuing to push the envelope thanks to an eccentric Timbaland production. Barack Obama alluded to this song during his 2008 presidential run, brushing off then-rival Hillary Clinton’s attacks, solidifying his connection to hip-hop, and immortalizing a Hov classic.

46. “Part II (on the Run),” Magna Carta … Holy Grail (2013): The latest episode in Jay-Z and Beyoncé’s Bonnie and Clyde saga (11 years after the original!) is endearing, like the musical equivalent of renewing wedding vows.

45. “You Must Love Me,” In My Lifetime, Vol. 1 (1997): Early in his career, Jay was best known for flaunting the spoils of his lucrative drug-dealing past. But this emotional number evinces underlying shame — dwelling on the distress he inflicted upon his mother and the actual bullets he inserted into his brother’s body. It was the first time Jay-Z truly opened up his closet for the world to see his skeletons.

44. “Change Clothes,” The Black Album (2003):

Puff Daddy suggested an evolved stage of personal development every time he switched up his aliases; Jay-Z accomplished the same by buying a new wardrobe and then rapping about it. Before the age insecurities of Kingdom Come set in, Jay was proud to mature his sound and image (and push now-clichéd phrases like “grown and sexy”). He gets a nudge here from the Neptunes’ sophisticated piano-based instrumental.

43. “Song Cry,” The Blueprint (2001): One year after famously rapping “have an affair, act like an adult for once,” Jay-Z shares a cautionary tale describing the fallout of that playboy lifestyle. It’s not as emotional as the title suggests, but you can hear the remorse in his voice, albeit only slightly, as he reconciles with how his immaturity and selfishness ended a happy relationship and forever corrupted a “good girl.”

42. “Politics As Usual,” Reasonable Doubt (1996): Flashy rhymes and mafioso imagery laid over a glittery Stylistics sample — it’s all a day in the life of Jay-Z.

41. “Allure,” The Black Album (2003): There’s so much sincerity in this song about the irony of the hustler’s plight — the idea of becoming addicted to the illegality of selling drugs. Even as one of hip-hop’s richest figures, Jay couldn’t shake the craving for that adrenaline rush, despite knowing and imagining the very real risks in detail. He’s almost longing for one more moment in the trap house, over the Neptunes’ yearning piano keys and synthesizer. If The Black Album is a tentative good-bye to music, then “Allure” is Jay’s reluctant sayonara to the drug game that made him.

40. “Jigga My Nigga,” Ruff Ryders’s Ryde or Die Vol. 1 (1999): Just as Jay-Z was becoming a superstar, Swizz Beatz turned his name into a jingle. The Ruff Ryders producer had Eve and Amil sing Jay’s moniker on this song’s hook, further implanting it into the minds of listeners and keeping his hot streak sizzling, even as Hov rapped with an unshakeable cool.

39. “Renegade,” The Blueprint (2001): Lyrically, this is one of the best bar-for-bar collaborations in Jay-Z’s discography. He and Eminem play on the concept of being America’s nightmares, punching bags for the critics and naysayers who’ve never walked in their Nike Airs. Slim Shady edges Jay out with his twisted rhyme flow and religious imagery, but the lyrical square-off is much less lopsided than Nas’s “Ether” suggests (“Renegade” started as a collaboration between Royce da 5’9” and Eminem, who made the beat, so Jay didn’t really have home-court advantage, either.)

38. “New Day,” Watch the Throne (2011): Not only just a song anticipating fatherhood, “New Day” is a reflection on Kanye and Jay’s own lives — respective plans to shield their future sons from the pain and regrets that they’ve experienced. The distorted Nina Simone sample adds a mystical feel.

37. “Encore,” The Black Album (2003): “Encore” plays perfectly into The Black Album’s retirement campaign — it’s a not-so-subtle comparison between his supposedly concluding career and the closing stages of a live performance. Contrived as it was, the analogy is ingenious. Not only is the song perfect for live shows, it also accomplishes the crafty trick of grieving Jay-Z while he’s still alive, with its weeping trumpet. Fans bought into it, despite several lyrical hints that suggest he’ll never stray too far away from the recording booth.

36. “Friend or Foe,” Reasonable Doubt (1996): The rare prequel that’s bested by its final chapter, “Friend or Foe” is all about Jay’s aplomb. There’s no bluster here, just menacing, smoothly delivered demands laid over Preem’s chilly horns.

35. “Do It Again (Put Ya Hands Up),” Vol. 3 … Life and Times of S. Carter (1999): This irresistible toast to a recurring party life is the song you’d want playing when you enter the club with your closest compadres in tow. Beanie Sigel drops one of his finest verses, portraying the dangerous nightclub junction where both bottles and guns might pop.

34. “Coming of Age,” Reasonable Doubt (1996): Jay-Z came into the rap game as a made man — a point underscored by his role in this story that doubles as the world’s introduction to Memphis Bleek. The song — completely penned by Jay — positions Hov as an OG seeking a hustler apprentice. It’s a masterful recruitment that presents the eager Bleek and streetwise Jay effectively.

33. “Murder to Excellence,” Watch the Throne (2011): The most powerful moment on Watch the Throne — and the thematic crux of the entire album — finds two of hip-hop’s most important voices going for five minutes about police brutality, black unity, crashing through glass ceilings, and why the best revenge is your paper.

32. “22 Two’s,” Reasonable Doubt (1996): More than just a cheap party trick, this Ski-produced track exhibited Jay’s advanced wordplay and showman abilities from his very first album.

31. “Moment of Clarity,” The Black Album (2003): Jay-Z offers a front-pew seat at his father’s funeral. His honesty is touching — how are you supposed to react to the loss of someone you barely knew, whose DNA comprises half of your own? It’s an emotional boggler that Jay articulates deftly: “Pretending to be hurt wouldn’t work / So a smirk was all on my face / Like, ‘Damn, that man’s face is just like my face.’”

30. “Friend or Foe ’98,” In My Lifetime, Vol. 1 (1997): DJ Premier’s instrumental is harder and more dramatic than that of Reasonable Doubt’s origin story, in which Jay-Z intercepts a rival hustler who’s encroaching on his territory. Jay’s delivery on this climactic sequel is equally aggravated, but he stays in character — super cool, even letting off a few wisecracks before sending the poor guy to meet his maker with a couple of ice cubes and a friendly shoutout to Biggie.

29. “This Can’t Be Life,” The Dynasty: Roc La Familia (2000): An essential track in establishing Roc-A-Fella’s signature sped-up sample aesthetic. Kanye’s flip of Harold Melvin & the Blue Notes’ classic “I Miss You” is tender and wistful, the perfect backdrop for Beanie, Jay, and Scarface to get personal about their pasts, presents, and futures.

28. “Where Have You Been,” The Dynasty: Roc La Familia (2000): This is perhaps the most emotive on-wax scolding of deadbeat dads in existence. You can just hear the vulnerability. Beanie Sigel is audibly in tears. At times, Jay-Z raps through clenched teeth. A harrowing Camilo Sesto sample sets the mood as the two rappers unload years of hurt, using their platform to chew out absentee fathers.

27. “Ain’t No Nigga,” Reasonable Doubt (1996): This update of the Four Tops’ “Ain’t No Woman” put Hov on the map, helping him land his deal with Def Jam and a coveted slot on the Nutty Professor soundtrack. Jay and an amped Foxy Brown — then still a teenage rapper on the rise — throw playful negs at each other throughout, beginning a musical harmony that’d last for years.

26. “Nigga What, Nigga Who (Originator 99),” Vol. 2 … Hard Knock Life (1998): A welcome return to Jay-Z’s rapid-fire flow, finding a home over Timbaland’s thumping bass line and crisp snares. It’s a developed evolution, a tempering of his double-time delivery that’s easier to keep up with than past speed raps, yet still dazzling to both day-one fans and newcomers to the bandwagon.

25. “Izzo (H.O.V.A.),” The Blueprint (2001): Besides helping to push the Snoop Dogg–popularized “-izzle” slang to caricature, this lead single from The Blueprint gave a Jackson 5 sample new life and Jay-Z his first top-ten Billboard Hot 100 appearance.

24. “Otis,” Watch the Throne (2011):

The quintessential Jay and Kanye collaboration. The two emcees take turns making claims that might sound ridiculous being spat by anyone else, upping the ante with every line. Jay has two Rolex watches; Kanye has three Benzes. Yeezy hints at birthing Drake’s style; Jigga insinuates that he predates an entire “swag rap” subgenre. Hov can buy political asylum; Kanye is protected from eternal damnation. All of this boasting takes place over a sputtering Otis Redding sample that’s a welcome progression from Kanye’s early soul loops.

23. “Lucifer,” The Black Album (2003): Kanye’s sample of Max Romeo’s “Chase the Devil” establishes a spiritual element in a song about retribution, as Jay-Z lashes out against the unknown (or inaccessible) killers of his friends.

22. “Regrets,” Reasonable Doubt (1996): Reasonable Doubt is an album that presents Jay-Z’s experiences as an avatar for hustlers who’ve run the same Brooklyn streets as him. Here, he gets a bit more personal, using tension brilliantly throughout. In one verse, Jay has a conversation with a deceased friend; in another, he recalls coming this close to being busted in a sting operation. Overall, the song is about morality and facing the guilt that comes with participating in the dark world that Jay depicts on his debut — it’s not unlike the shame of an addict coming off of a high, knowing they can’t escape the substance that’s most destructive to them.
“Regrets” is a sobering album outro that furthers the complex, conflicted persona that is Shawn Carter.

21. “Money, Cash, Hoes,” Vol. 2 … Hard Knock Life (1998): As urban legend has it, an epic battle between Jay-Z and DMX went down in the early ’90s at a pool hall in the Bronx. Things reportedly got tense; the winner of the face-off varies based on who you ask. The two emcees would appear on tracks in the years that followed, but “Money, Cash, Hoes” was the perfect storm. By then, X was New York’s grittiest emcee, coming off of a massively successful debut LP. Jay was all about flossing, but had the ear of the streets as well. They collided here over a genius Swizz Beatz track, which samples “Theme of Thief,” music that appears in the 1989 video game Golden Axe. The result: A hard-knock anthem that set the stage for two once-in-a-generation rappers to rule hip-hop for years to come.

20. “Run This Town,” The Blueprint 3 (2009): This song started out as a Rihanna demo and went on to become a grand opening for Roc Nation and one of the most successful singles of Jay’s solo career. His two greatest musical protégés shine: Rih’s vocals are perfect, like a war cry with a touch of rasp, and Kanye, who’s claimed he spent a month writing his verse, aggressively expresses his love-hate relationship with stardom (and drops a memorable RAV4 un-endorsement). As for Jay, he births the oft-quoted phrase “all-black everything” here.

19. “Streets Is Watching,” In My Lifetime, Vol. 1 (1997): The opening line, “If I shoot you, I’m brainless / But if you shoot me, you’re famous,” is perhaps the truest assessment of the conundrum facing former outlaws in the public eye. This standout from Vol. 1 is like a savvy manual on how to rise from a life of crime without blowing it once you make it big. The final verse colorfully runs down Jay’s criminal capers over Ski’s epic string sample.

18. “Feelin’ It,” Reasonable Doubt (1996): The skeleton of this song originally belonged to NYC rhyme duo Camp Lo, who gifted it to Jay when they realized it didn’t fit the sound of their own debut album. Jigga took that sung hook and gorgeous piano loop — courtesy of Ski — and transformed them into a melodic single that added a fleck of R&B soulfulness to a classic album that’s heavy on intricate raps.

17. “U Don’t Know,” The Blueprint (2001): One of Jay-Z’s most high-powered anthems gets its oomph from a Bobby Byrd sample that Just Blaze distorted and pitched up beyond recognition. The awesome instrumental is the product of a friendly in-studio beat battle with Kanye West. While Just Blaze wasn’t satisfied with the final beat (hence the upgraded M.O.P.-featured remix on The Blueprint²), it was a fitting soundtrack for Jay-Z to count his millions and boast about his hustler forte.

16. “Can’t Knock the Hustle,” Reasonable Doubt (1996): This mid-tempo track is an appropriate introduction to Reasonable Doubt — it’s Jay’s formal musical announcement to his buddies on the block that his hustling days are over and hip-hop is the new moneymaker. But the hit single, which nicely renovates Meli’sa Morgan’s 1986 track “Fool’s Paradise,” almost didn’t happen. According to Damon Dash, Jay was hesitant to rap over the beat. But it all came together once they got the hottest singer in hip-hop and R&B, Mary J. Blige, to bless the track with her vocals as a personal favor — Dash says they paid her $10,000 in a brown paper bag, just pennies compared to the greenbacks Jay flaunts in this song’s stanzas.

15. “Can I Get A …,” Vol. 2 … Hard Knock Life (1998): Jay-Z cashed in on the insecurities of moneyed men with this megahit that shuns gold-digging women. He made it a true battle of the sexes by inviting Roc-A-Fella’s newest artist Amil, penning an assertive verse for her to counter his own. Her voice adds a distinctive touch; light like whip cream with a dollop of sass: “You ain’t gotta be rich but fuck that / How we gonna get around on your bus pass?” she asks, just months before TLC dropped “No Scrubs.” But “Can I Get A …” all started in the mind of Ja Rule, then an up-and-coming Queens rapper who wrote the hook and gave the song to Jay in exchange for a feature slot. The three artists made history by pondering what matters most: the size of a man’s heart or his bankroll. All these years later, the question is still up for debate.

14. “99 Problems,” The Black Album (2003):

Jay-Z was inspired by Ice-T’s 1993 song of the same name — according to Rick Rubin, it was Chris Rock’s suggestion. But Jay made the concept his own, using Rubin’s raucous electric guitars as an ambience to slam music media and call out prejudiced cops, complete with a mocking southern accent.

13. “Where I’m From,” In My Lifetime, Vol. 1 (1997): A walk around the perimeters of Jay-Z’s hood that offers a high-definition look at Marcy Projects in all of its beauty and horror. Both the lyrics and monstrous bass line will shake you to your core, as Jay portrays the lives of shooters, pimps, prostitutes, hustlers, ballers, rappers, and trigger-happy police officers — a far cry from the gentrified Brooklyn blocks that exist in the area present day.

12. “Takeover,” The Blueprint (2001): Many believed “Takeover” to be a knockout blow before Nas retaliated with his own haymaker, “Ether.” But musically, this is bigger than just a battle song. Kanye West chopped up a crazy sample from the Doors — taming the unruly guitar strings — and got the hell out of the way. Jay presents a slideshow of his adversaries’ shortcomings and missteps, humiliating Mobb Deep and portraying Nas as a fraudulent hip-hop has-been; the addition of David Bowie’s altered faaame sound bite is a shrewd touch as well. The gloves are off, and Jay taught a new generation how to pick apart an enemy.

11. “Niggas in Paris,” Watch the Throne (2011):

Okay, no, this is the quintessential Jay and Kanye collaboration. The title in itself is radical, a dissonance inspired by attending the most exclusive Parisian fashion shows while listening to Young Jeezy. Quotables abound, especially from Kanye (“What she order? Fish filet”), but Jay reminds you that more than extravagance, this song is a celebration of life itself — statistics say the two artists were exponentially more likely to be dead or in jail than mingling in the upper echelon of fortune and fame. Hit-Boy instantly became a go-to producer after lacing these hypnotic synths that give way to explosive drums.

10. “D’Evils,” Reasonable Doubt (1996):

This is the darkest moment on an album full of green-splattered fantasy and criminal atrocity. Over a solemn DJ Premier instrumental, Jay-Z depicts the evil that can possess those who live in poverty, creating monsters who are driven by greed and a craving for power. Jay says he dreamt the first bars of this song, but verse two is more like a nightmare: He imagines a tale of treachery in which he turns on a childhood friend, kidnapping and bribing the mother of his child, and implying their impending demises. As a wordsmith, it’s Jay at his most macabre.

9. “Dead Presidents” / “Dead Presidents II,” Reasonable Doubt (1996):

Take a listen to the original Lonnie Liston Smith piano loop sampled for this standout chapter in the Jay-Z canon; it’s cold and beautiful — the sound of loneliness. Ski sped up that melody, threw some drums beneath, and a classic Nas vocal chop on top to create the soundscape for Jay to revel in the highs and lows of hustling. Both versions feature the same beat — the sequel is merely a means to update the superior original — and a total of five thoughtful verses from Jay that still stand as some of his most cunning lyricism.

8. “I Just Wanna Love U (Give It 2 Me),” The Dynasty: Roc La Familia (2000):

The sentiment of this timeless smash hit came from a party thrown by Kimora Lee Simmons. Jay remembered seeing Mary J. Blige dancing to Carl Thomas’s “I Wish,” which Jay karaokes with some of his best bad singing. The track is a magical combination of Jay-Z’s feel-good rhymes and the Neptunes’ funky bass lines, which helped make the Virginia music men household names.

7. “Public Service Announcement (Interlude),The Black Album (2003):

This is a dynamite stick in Jay-Z’s live set. At the last minute of The Black Album’s recording, Just Blaze lifted an explosive riff from Little Boy Blues’ “Seed of Love” — suspenseful piano chords that give way to a jolting organ. Jay took that dramatic melody and ran with it. His first verse is all spelled-out flows, declarative bravado, and sneaky puns. The second is largely inspired by journalist Elizabeth Méndez Berry, who attended a preliminary album playback for media. She questioned the contradiction of Jay wearing a diamond necklace over a T-shirt depicting Marxist revolutionary Che Guevara, before handing him an acerbic critical essay that she wrote about his past music. And hence, Hov spits “I’m like Che Guevara with bling on, I’m complex” to open a stanza that’s introspective and almost defensive when explaining how his past shaped his current objectives. Ultimately, the track is a Jay-Z mission statement that also happens to be one of the most memorable songs of his career.

6. “Brooklyn’s Finest,” Reasonable Doubt (1996):

This classic back-and-forth lyrical slugfest between two of the absolute best to ever do it started as a solo cut called “No More Mr. Nice Guy.” Once the Notorious B.I.G. was onboard, Jay altered his verses so he could trade friendly fire with the reigning king of N.Y., and changed the title to something more precise. You can hear each verse upping the ante for the next. “From ’9-6, the only MC with a flu / Yeah I rhyme sick, I be what you’re trying to do,” Jay challenges, only for Biggie to counter with his own sick punch line, “Gotta go, Coolio mean it’s getting ‘Too Hot’ / If Fay’ had twins, she’d probably have two ’Pacs.” Decision is split on whose performance is toughest (I’d take Big by a whisker), but the song is one of the most intense and enjoyable rap duets Jay ever recorded.

5. “4:44,” 4:44 (2017):

This is what a sincere version of “Song Cry” might sound like. A track that doesn’t make light of matters of the heart with flippant rationale like, “I was just fuckin’ those girls, I was gon’ get right back.” No, this one is full of genuine remorse. Real heartache. Jay-Z airs out his indiscretions over a tortured sample of Hannah Williams & the Affirmations’ “Late Nights & Heartbreak,” issuing an open apology to Beyoncé for missing the mark as a husband in more ways than one. “I never wanted another woman to know / Something about me that you didn’t know,” he rhymes, shamefaced. He sounds at his most repentant when wondering if his children will one day see him differently after learning of his mistakes. “4:44” raises Jay-Z’s bar for emotive music, once again proving that the best music often arises from places of pain.

4. “Empire State of Mind,” The Blueprint 3 (2009):

Prototypical NYC anthems like Billy Joel’s “New York State of Mind” or Frank Sinatra’s “Theme From New York, New York” tend to be sugarcoated, pandering to the ideals of tourists who’ve never stepped foot in the Big Apple. Jay keeps those archetypes in his Alicia Keys–guested “Empire State of Mind” — shouting out the city’s yellow cabs and major sports teams — but adds a heavy dose of realism, also showing its perilous underbelly. The result makes for an interesting juxtaposition between Keys’s celebratory vocals and Hov’s lyrics about prostitution. Grand and gritty, a proper hip-hop ode to Gotham City.

3. “Big Pimpin,’” Vol. 3 … Life and Times of S. Carter (1999):

Timbaland’s flute sample in “Big Pimpin’” has the power to instantly teleport you to somewhere much hotter and more tropical than your current location. For Jay, it helped relocate him to a high slot on the pop charts, and granted Texas duo UGK — who arguably upstage Hov here — the most successful song of its career. Bun B’s unorthodox flow sounds right at home, but Pimp C’s bouncy, fun verse has aged best. The opposite can be said for Jay’s savage, misogynistic rhymes. “What kind of animal would say this sort of thing?” he wrote in Decoded years later. Still, “Big Pimpin’” was an important moment in cementing Jay’s status as a reliable hit-maker, and helping to eliminate hip-hop’s already-shrinking regional divide.

2. “Can I Live,” Reasonable Doubt (1996):

This is all sonic dramatics and verbal acrobatics. The beat, built on a sample of Isaac Hayes’s “The Look of Love,” feels like a scene in a gangster flick — producer Irv Gotti was inspired by the film Dead Presidents. On the track, Jay evokes paranoia and affluence and introspection via multisyllabic flows that offer a deeper psychological analysis of the mind of a hustler. It’s lyrically one of Jay’s best showcases, a perfect example of why Jay-Z is one of the best rappers of all time.

1. “Hard Knock Life (Ghetto Anthem),” Vol. 2 … Hard Knock Life (1998):

Broken down in the simplest form, Jay-Z’s career exists in two acts: before and after this song’s existence. “Hard Knock Life (Ghetto Anthem)” changed the course of Jay-Z’s career and made his life and times understandable (and captivating) to millions. Mark the 45 King’s Annie sample is the not-so-secret sauce on this whopper of a hit record — vocals of the orphaned characters portray a beautiful struggle that’s both the furthest thing from hip-hop and its epitome. Jay’s street-conscious lyricism oozes authenticity and bridges the gap, making this song a crown jewel in his discography.

All 274 Jay-Z Songs, Ranked From Worst to Best