The 100 Best Simpsons Episodes to Stream

Photo: FOX

The Simpsons is having a moment. After over two decades on the air and 552 episodes, the show feels more relevant now than it has at any point since its prime. In addition to the show celebrating its 25th anniversary on the air (the 26th season debuts this Sunday, Sept. 28, at 8 p.m. on FOX), in October, FX will launch "Simpsons World" within its FXNOW app. For the first time, anyone will have the ability to stream any episode on demand. This is truly unprecedented access to the entire series, especially for those too young to have seen older seasons and those once-loyal fans who might've abandoned the series along the way.

As part of Vulture's Streaming Week — in which we look at the ways in which web series and ascendant services like Netflix, Hulu, and Amazon are changing the way we watch TV — we have assembled the 100 essential Simpsons episodes. It's a guide for fans both young and old, and for those who have yet to even see a single episode. In the same way that the “Every Simpsons Ever” marathon succeeded in connecting the legacy of the classic seasons with the later ones, our list reflects the show's continued greatness over two and a half decades. It includes the first episode and one of the most recent. These 100 episodes best paint a picture of all the things the series does best. And to enrich your experience, you can sort the list according to when the episode first aired and by which family member has a starring role. Happy streaming!


Cape Feare

(Season 5, 1993) #1 in our Top 100

As close to a perfect half-hour as TV has produced, “Cape Feare” springs the giant-footed maniac Sideshow Bob (Kelsey Grammer) from prison and returns him to Springfield on a mission of revenge, with musical interludes. It’s ostensibly a parody of the thriller Cape Fear (more the 1991 Martin Scorsese remake than the 1962 J. Lee Thompson original), has a similar-sounding score, and it hews closely to that template, which gives the episode a propulsive quality that’s unusual for this digressive show.

But even as the episode pours on horror-movie-style incidents—referencing Psycho and A Nightmare on Elm Street as well as Cape Fear, driving the family into witness protection in a houseboat on Terror Lake, and replaying the show’s opening credits as “The Thompsons”—it somehow makes room for multiple, marvelous sight-gags and exchanges in each scene. These run the gamut from Mel Brooks–level shticky (Sideshow Bob telling the parole board that his “Die, Bart, Die” tattoo is “German for ‘The Bart, the’”) to subtle (Bob’s Night of the Hunter–styled “Love” and “Hate” tattoos read “luv” and “hat” because Simpsons characters only have four fingers), to so drawn-out that they verge on anti-humor (Bob stepping on rake after rake). By the time we get to the finale, with Bart stalling for time by convincing the vain Bob to sing the complete score to Gilbert & Sullivan’s “H.M.S. Pinafore,” the episode has entered the realm of the sublime. Anne Washburn’s 2013 experimental stage drama Mr. Burns envisioned a postapocalyptic world in which the plot of “Cape Feare” is handed down with reverence, as if it were Oedipus Rex or the story of Cain and Abel. Sounds plausible to us.


Last Exit to Springfield

(Season 4, 1993) #2 in our Top 100

Lisa’s need for braces coincides with Mr. Burns’s attempts to take the nuclear-plant union’s dental plan away. Homer runs for union president and wins; the ever-overreaching Burns is vilified as the cartoon bad guy that he absolutely is, while misinterpreting Homer’s density as tactical brilliance.

This is another structurally brilliant episode, building inexorably toward a marvelous Dr. Seuss parody that presents Burns as a Grinch (shutting off Springfield’s electricity) and the striking workers, egged on by a guitar-strumming Lisa in Woody Guthrie mode, as the Whos down in Whoville. Along the way, the episode serves up some of the series’ best cutaway gags (the Jimmy Hoffa–like fate of Homer’s predecessor; Lisa’s Yellow Submarine–style anesthesia fantasy; a montage showing what happens when Burns and Smithers replace the strikers with robots).


Marge vs. the Monorail

(Season 4, 1993) #3 in our Top 100

Piling incident upon incident and gag upon gag, this episode-length affirmation of Springfield’s gullibility will continue to be quoted whenever public works are discussed. The late, great Phil Hartman guest-stars as Lyle Lanley, who convinces the citizenry to spend an unexpected windfall on a monorail.

Interweaving pop-culture parody and social satire in the best Simpsons tradition, “Marge vs. the Monorail” is a treasure trove of quotable bits and indelible moments, many of which brush against the surreal. Lanley enters the episode at a town meeting, duded up like Professor Harold Hill and leading the room in a call-and-response sing-along modeled on The Music Man’s “(Ya Got) Trouble” (“Were you sent here by the devil?” “No, good sir, I’m on the level!”). Leonard Nimoy guest-stars as himself, boring people with Star Trek anecdotes, mocking his propensity for grandiose voice-overs (“The cosmic ballet continues”) and exiting the story in a transporter-style energy beam. The final shot—a roll call of future public-works scandals, confirming that Springfield learned nothing from this disaster—is oddly poignant.


The Itchy & Scratchy & Poochie Show

(Season 8, 1997) #4 in our Top 100

When Krusty the Clown gripes that the tiredness of Itchy and Scratchy is sinking his ratings, the producers try to rejuvenate the bloody cartoon by adding a new character, Poochie, a surfing, rapping, to-the-extreme dog created via network meddling and focus-group sessions with kids who have no idea what they actually want.

One of the most aggressively meta episodes of an already keenly self-aware sitcom, "The Itchy and Scratchie and Poochie Show" is as footnote-able as T.S. Eliot's "The Waste Land." It nearly renders criticism moot, since it pretty much analyzes itself—and the broadcast network system that produced it—as it goes along. It's a poison-pen letter to commerce interfering with art (Homer, who eventually voices the character, destroys his new gig by offering dim-witted notes of his own), but the dose goes down easy thanks to the sweetness of Lisa and Bart, who point out that every great TV show starts to seem tired if it’s around long enough, and that it's not a bad idea to remember that their creators are giving fans hundreds of hours of entertainment for free. ("Worst episode ever," the Comic Book Guy repeats, undeterred.) Poochie doesn't last long, and his demise is brutally funny: Homer's voice-over cuts off and is replaced by another actor who sounds nothing like him, and we see animators physically ripping away the animation cel that contains the offending canine. The show's crowning touch is the sudden and unexplained appearance in the Simpsons household of Poochie’s doppelgänger, a teenager named Roy who, calls Homer "Mr. S.," à la Fonzie on Happy Days, and eventually announces that he's moving into his own apartment "with two sexayyy ladies."


Lisa’s Substitute

(Season 2, 1991) #5 in our Top 100

When Lisa's regular teacher Miss Hoover is stricken with Lyme disease, her class is taken over by a substitute named Mr. Bergstrom (guest-star Dustin Hoffman), a gentle, funny, guitar-strumming, everybody's-best-friend-and-mentor type. Lisa develops a crush on him, fueled mainly by her realization that Bergstrom's sensitivity and love of learning fill needs that her often brutish and anti-intellectual dad isn't equipped to handle.

Arriving near the end of season two, "Lisa's Substitute" was one of the best early Simpsons episodes to operate almost entirely in "sweet" mode (though it has its share of pop-culture references, such as Miss Krabappel trying to seduce Mr. Bergstrom à la Hoffman's breakthrough The Graduate). It’s uncharacteristically reserved, and its final sequence—which finds Homer realizing some of his flaws as a dad and reaching out to his daughter to the extent that he can—is genuinely touching. This is also the first Simpsons episode in regular run to compact its opening credits and cut straight to the couch gag (in this case, a repeat of the one from season two's "Itchy and Scratchy and Marge," in which the family enters the living room and finds the couch missing).


Treehouse of Horror V

(Season 6, 1994) #6 in our Top 100

One of the very best of The Simpsons’ annual Halloween-themed anthologies, “Treehouse of Horror V” riffs on The Shining, time-travel stories, and Soylent Green, with the usual compressed encyclopedia of pop-culture jokes and hyperviolent sight gags mixed in.

In “The Shinning,” the family moves into Mr. Burns’s mansion while he’s away, but Mr. Burns’s decision to keep Homer focused by cutting off the cable TV and his beer supply sends him into a Jack Torrance–style insanity spiral (enabling co-star Dan Castellanata and the animators to give a tour-de-force performance as Homer channeling Jack Nicholson in hambone mode). In “Time and Punishment,” Homer accidentally creates a time machine while fixing a broken toaster, leading to a flurry of quick-cut riffs on time-travel logic, many of them spinning off the punch line of Ray Bradbury’s classic short story “A Sound of Thunder,” in which the death of one butterfly changes everything. In one timeline, Homer is thrilled to discover that his dreaded sisters-in-law Patty and Selma are dead, but that the world no longer has doughnuts. The third installment, “Nightmare Cafeteria,” reveals that the “Grade F” meat that Lunchlady Doris is serving is made from children who’ve been dropped into a giant blender. The out-of-nowhere final gag, which sees the family turned inside-out by a creepy blue fog (based on an old-time radio episode), is the grossest touch of all; supposedly producer David Mirkin made a point of upping the violence in this one after network notes warned him that the last few Treehouses had been too bloody.


Lisa the Vegetarian

(Season 7, 1995) #7 in our Top 100

After doting on a lamb at a petting zoo, Lisa decides she’s done eating meat; everyone in town, including her own family, ridicules or resists her. "What's the difference between this lamb and the one that kissed me?" Lisa asks her family, pushing her dinner plate away. “This one spent two hours in the broiler!" Homer declares. But she perseveres in her beliefs. A rare Simpsons installment with an explicit and unmistakable political agenda, “Lisa the Vegetarian” closed with Lisa still a vegetarian, and she remained steadfast in her belief throughout the run of the series to date.

Shepherded by then-showrunner David Mirkin, who had recently renounced meat, the episode puts Lisa’s integrity front and center while acknowledging how hard it is to stick to one’s beliefs if they represent a minority view. When Lunchlady Doris learns of Lisa’s decision, she sets off an “Independent Thought” alarm, and Troy McClure proclaims, "If a cow ever got the chance, he’d eat you and everyone you care about." The episode is typically rich with incidental silliness, including Ralph Wiggum’s “Oh, boy, sleep! That's where I'm a Viking!"


Deep Space Homer

(Season 5, 1994) #8 in our Top 100

In an attempt to boost public interest in the space program, NASA decides to send an ordinary person — Homer Simpson, natch — into space alongside astronauts Race Banyon and Apollo 11 astronaut Buzz Aldrin, giving the writers of The Simpsons a golden opportunity to make every science-fiction joke imaginable. The training sequence requires Homer’s crew mate Barney to go without booze, unleashing his inner gymnast and opera singer (he performs two lines of the Major General’s song from The Pirates of Penzance; shades of “Cape Feare”), and Homer’s fears of space travel are realized when he opens a bag of smuggled potato chips in zero gravity and causes an Apollo 13–style crisis.

Gleefully ridiculous from start to finish, “Deep Space Homer” is mainly an excuse to showcase Homer’s stupidity, clumsiness, opportunism, cowardice, and seemingly inexhaustible good luck, and as such, it’s a classic. Great spoof moments abound (Homer’s zero-gravity chip-munching ballet set to “The Blue Danube” is one of the best of The Simpsons’ Stanley Kubrick shout-outs), as do the kind of casually bizarre flourishes that the show does so well. Homer loses the plant’s Employee of the Month contest to an inanimate carbon rod that ends up stealing his space-hero glory, too, earning a ticker-tape parade and a magazine cover that announces “In Rod We Trust.”


A Star Is Burns

(Season 6, 1995) #9 in our Top 100

Sending up film festivals, film critics, the artist’s mentality, and the anti-intellectual tendencies of American culture, “A Star Is Burns” is one of the series’ rare crossover episodes (with the short-lived The Critic, by Simpsons producers Al Jean and Mike Reiss, which had recently come over to Fox after getting canceled by ABC). But any cross-creative awkwardness dissipates once critic Jay Sherman (guest-star Jon Lovitz) touches down in Springfield to judge its first-ever film festival.

This is a Simpsons episode that makes you laugh and cringe at the same time for the way it critiques Springfield’s lack of sensitivity even as it’s mining it for laughs. It’s also a terrific sendup of nearly every film festival in existence, as all the entries unwittingly reveal their creators’ mentalities, often in unflattering ways. Bart’s entry is just cruel hidden-camera footage of his dad trying to squeeze into too-small pants; Ned Flanders makes an amateurish film about Moses that sends one of his children careening down a river; Hans Moleman’s “Man Getting Hit in the Groin by Football” is self-explanatory. Barney, as is often the case, reveals unexpected refinement, directing a black-and-white psychodrama about his alcoholism, but Homer, who’s on the judging panel, prefers the one with the football in the groin. Barney wins, but Homer is right, in a way: Hans Moleman’s short film is remade with George C. Scott and wins an Oscar.


Summer of 4 Ft. 2

(Season 7, 1996) #10 in our Top 100

On a devastating last day of school—one of too many to count on this time- and geography-blurring series—Lisa is bereft when nobody will sign her yearbook. Marinating in despair over her unpopularity, she resolves to reinvent herself during a family vacation to a beachside town, amping up the symbolism by bringing along an empty suitcase. Her new persona is an anti-intellectual "cool" girl.

Like a lot of Lisa-centric episodes, this one cuts to the heart of a young girl's struggle to invent an identity for herself without being dishonest about her nature. That might be why it's lighter on belly laughs than a lot of the other episodes on this list, though it has its share of sly jokes, including Lisa mournfully regarding a picture of Gore Vidal and lamenting that he's "kissed more boys than I ever will." "Girls, Lisa," her mother replies. "Boys kiss girls."


Behind the Laughter

(Season 11, 2000) #11 in our Top 100

Although The Simpsons was always less worried about continuity than most TV shows, "Behind the Laughter" set a new standard. Spoofing the VH1 series Behind the Music (with voice-over by that show's regular narrator, Jim Forbes), it's a rise-and-fall story that seems to occur not within the Simpsons universe, but adjacent to it. It's as meta as "The Itchy & Scratchy & Poochie Show," though in a different way.

Apparently, the family got into showbiz by producing a pilot for the show we're now watching, then became hugely successful, squabbled over money, split up, and did whatever they had to do to pay the bills before finally reuniting at the Iowa State Fair. The show's a treasure trove of in-jokes, some of them impossible to appreciate without inside knowledge (all the posters advertising the "fictional" Simpsons show are actually posters advertising the real thing), others broad as can be (when Bart gets kicked off the show for attacking flight attendants, he's replaced by Richie Rich). Throughout, there's a empathetic understanding of actual showbiz hazards: Homer becomes addicted to painkillers, Marge blows a lot of the family fortune on bad investments, and Lisa eventually pens a tell-all titled Where Are My Residuals?


A Streetcar Named Marge

(Season 4, 1992) #12 in our Top 100

Everyone remembers the A plot of this one—Marge somehow wins the role of Blanche DuBois in a community-theater production of a musical version of A Streetcar Named Desire, written and directed by Llewlyn Sinclair (guest-star Jon Lovitz)—and deservedly so. But the B plot, which finds Maggie getting socked away in day care and plotting a prison-movie-style escape, is just as strong, sweet, and funny.

This is a pantheon episode for the show's writers and its musical director, Alf Clausen. The daycare sequences reorchestrate Elmer Bernstein's score for The Great Escape, and the musical's brazenly silly earworms include "You Can Always Depend on the Kindness of Strangers" and "New Orleans." The latter's hyperbolically grim lyrics describing the Big Easy as "stinking, rotten, vomity, vile" caused an outcry in the city; the series apologized the following week by having Bart write "I will not defame New Orleans" on the opening credits' chalkboard.


Home Sweet Homediddly-Dum-Doodily

(Season 7, 1995) #13 in our Top 100

Although The Simpsons has always been aware of how chaotic the kids' home lives are, they never really dealt with it on somewhat real terms until this episode, which finds Homer and Marge going away for a spa vacation. They leave Bart, Lisa, and Maggie under the care of Grandpa Abe, who botches the job so badly that Child Protective Services takes them away, names the Flanders as their foster parents, and informs Marge and Homer that they can't get their kids back until they take a parenting class. Bart chafes at Ned and Maude's God obsession and strictness, but Lisa finds that she appreciates the routine.

"Home Sweet Homediddly-Dum-Doodily" has that perfect mix of sentiment and silliness that defines so many classic episodes. The entire episode has an undercurrent of dread leavened by absurdity: When Lisa and Bart come home from school, respectively, shoeless (thanks to bullies) and wrapped in a burlap sack (his clothes burned to prevent the spread of lice), it's funny but also horrifying because the kids are genuinely distressed. Of course, in the end, we root for Marge and Homer to get their kids back, mainly because the Flanders overstep their bounds, trying to baptize the kids in a menacingly filmed sequence that would be offensive if the climactic gag—Homer recoiling from the baptism water like a vampire—didn't suggest that in some sense, God is on the side of the righteous.


A Milhouse Divided

(Season 8, 1996) #14 in our Top 100

Marge tries to get out of one of her periodic ruts by throwing a dinner party at the Simpsons home and inviting the Flanderses, the Hibberts, the Lovejoys, and the Van Houtens, but Milhouse’s parents have a fight that cracks open the fissures already weakening their marriage, leading them to divorce. Kirk loses his job and tries rather pathetically to reinvent himself as a single guy, even dating a radio-station employee named Starla and recording a demo; Luann has better luck, hooking up with an American Gladiator who goes by the name of Pyro.

"A Milhouse Divided" pulls off that Simpsons trick of digging into incredibly painful real-life situations with enough humor that the experience doesn't become unpleasant. Its core is the way that people take their significant others for granted or fail to read and respond to their distress until its too late. The episode ends with one of Homer's patented brilliant-stupid Hail Mary passes that somehow manage to connect: He secretly divorces Marge so that he can propose to her and redo their substandard wedding, including the "reception," revealed in flashback as the two of them eating a Carvel cake at a truck stop.


Lisa’s Sax

(Season 9, 1997) #15 in our Top 100

After Bart chucks her saxophone out the window, Lisa is heartbroken. She can't remember her life before it, she says, which prompts Homer and Marge to tell her the saga of how the instrument came into their lives. "It all happened in 1990," Homer says. A 5-year-old Bart was miserable at kindergarten, a secretly gifted Lisa had nothing to stimulate her intellect, and Marge and Homer were scraping together $200 to buy an air conditioner. Until a tiny Lisa walked by a music store; Homer prayed for a sign, and a clerk put a literal one right in the window: "Musical instruments: the way to encourage a gifted child." In they go, and out they walk with one saxamaphone.

It's the perfect encapsulation of each character's true self: Homer is dopey, but ultimately very devoted; Marge is the voice of reason, but not a stick in the mud; Bart's mischievous and naughty, but only because he's looking for validation and companionship; Lisa feels a little underappreciated, but comes to see how much her parents really love her. Bonus points for the baby versions of Lisa, Bart, and especially Milhouse.


22 Short Films About Springfield

(Season 7, 1996) #16 in our Top 100

Equally inspired by 32 Short Films About Glenn Gould, Pulp Fiction (which it extensively references), and meandering, "whatever happens, happens" movies by the likes of Robert Altman and Richard Linklater, this is one of The Simpsons' most structurally daring episodes: essentially a grab-bag of short stories or vignettes or TV-show parodies connected not by plot but by theme, and sometimes by filmmaking devices (the transitions are unusually clever).

This also contains the immortal scene in which Principal Skinner invites Superintendent Chalmers over to his house for a meal, ruins it, and ends up serving him Krusty Burgers, which he passes off as "steamed hams." The Marx Bros. would approve.


Stark Raving Dad

(Season 3, 1991) #17 in our Top 100

When Homer's white work shirt gets stained pink in the wash, he wears it to work anyway, prompting Mr. Burns to label him an anarchist and send him to Dr. Marvin Monroe, who gives him a take-home psych evaluation that Bart fills out, landing Pop in an institution. There he meets a big white man who claims to be Michael Jackson, played, of course, by Michael Jackson.

The elapsed years have transformed this episode from a stunt episode made memorable by fine writing, acting, and direction into a poignant celebration of a great pop-culture icon whose voice was so unmistakable that the second you heard it, you knew that "Michael" really was who he claimed to be. The episode's B plot, Lisa worrying about her upcoming birthday, converges beautifully at the end, when Homer invites Michael to stay with them, and he mends fences between Lisa and Bart by convincing the boy to compose a song for his sister. The result, "Happy Birthday, Lisa," is a joy.


You Only Move Twice

(Season 8, 1996) #18 in our Top 100

An extended parody of James Bond in general and You Only Live Twice in particular, this is an almost entirely absurd episode that gins up world-changing events so that they can be forgotten the following week. Homer gets hired at the Globex Corporation, a mysterious company headed by a secret villain named Hank Scorpio; it’s a plum job that lets Homer work for a man who seems to genuinely like him, but Marge and the kids are unhappy with their relocation to Cypress Creek and want to return to Springfield. Homer’s attempt to discuss this conflict with his boss is interrupted by government troops attacking Scorpio’s headquarters. Things only get sillier from there.

A one-thing-after-another gagfest in mid-period Mel Brooks style, “You Only Move Twice” is one-stop shopping for Bond riffs. (The agent himself even makes an appearance and gets strapped to a table and menaced with a laser, à la Goldfinger, only he’s renamed “James Bont.” Occasional Simpsons guest-star Albert Brooks voices Scorpio, who, of course, sounds like an Albert Brooks character, hyperverbal and always hard-selling himself and his vision. Marge: “Mr. Scorpio, this house is almost too good for us. I keep expecting to get the bum’s rush.” Scorpio: “We don’t have bums in our town, Marge, and if we did, they wouldn’t rush. They’d be allowed to go at their own pace.”) The omnipotent malevolence of Bond villains is played for laughs here: At one point, Scorpio asks Homer if he likes France or Italy better, then launches a missile at Homer’s second choice, France. “Nobody ever says Italy,” Scorpio says.


Holidays of Future Passed

(Season 23, 2011) #19 in our Top 100

Longtime Simpsons showrunner Al Jean has said that "Holidays of Future Passed" was originally written to be a finale, just in case the cast members’ contract negotiations didn’t pan out. And you can sense it. By setting it in the future, it allows for the episode to have a backwards-looking, deeply nostalgic tone, focusing on Bart and Lisa's difficulty with parenthood as a way for them to look at their relationships with their own parents. Also, by setting it in the future, it allows for a lot of incredibly absurdist bits, like Bart's treehouse tree grumpily coming to life and revealing his resentment.

Speaking of the treehouse, it's there that a now grown-up (and drunk) Bart and Lisa have a very real, adult conversation about their respect for each other and the specific bond they share by growing up in the same house. It's one of the (many—we’re talking about 25 seasons here, people) most moving scenes of the entire series (partly thanks to Bart's court-mandated sincerity chip). "Holidays of Future Passed" just feels like the show operating at its very best. The heart, the satire, the absurdity, the one-liners: It all feels special in the way that the best episodes of The Simpsons feel like something beyond just a great episode of television. It would've been a perfect finale.


Radioactive Man

(Season 7, 1995) #20 in our Top 100

The long-awaited live-action-movie version of Radioactive Man is scheduled to shoot in Springfield, starring Rainier Wolfcastle in the title role. Bart auditions for the role of the hero’s sidekick, Fallout Boy, but loses it to Milhouse, who’s an inch taller. Milhouse is unhappy in the role because he only accepted it to appease his money-grubbing parents.

One of the most quotable Simpsons ever—a bold statement, admittedly—“Radioactive Man” stirs together an astounding number of The Simpsons’ ongoing obsessions, including jealousy between friends, comic-book mania, shifting pop-culture styles (apparently, the old Radioactive Man TV series is modeled on the 1960s Adam West Batman), and the way Hollywood warps innocence (Moe recalls his agonizing stint as a Little Rascal named “Smelly”). It’s also a star-making episode for regular cameo player Rainier Wolfcastle, who pronounces the hero’s catchphrase “Up and atom!” as “Up and at dem,” and responds to an onrushing tidal wave of acid with a monotone, “My eyes … de goggles, dey do nothing!”


Photos: FOX