When a show captures the zeitgeist of its time as well as Sex and the City did, viewing it from the distance of a decade or two brings its best and worst moments into much clearer focus. Now that we’re no longer wowed by the main four female characters’ then-revolutionary sexual freedom, we instead notice the power of Sarah Jessica Parker’s gut-punched, lovesick look at the end of the pilot episode. Now that we’re unfazed by a discussion about the pros and cons of becoming “Mrs. Up-the-Butt,” we can notice the richness of Charlotte’s journey from WASP princess to happy Jewish wife.
While researching my book Sex and the City and Us, I viewed and re-viewed every episode several times, marveling at plenty of new facets, noticing the major impact 9/11 had in the middle of this supposedly light-and-fluffy show, and cringing at plenty of outdated ideas along the way. Here, in honor of its 20th anniversary, is every episode of this sometimes problematic, sometimes infuriating, sometimes sublime — but no doubt seminal — show, ranked.
93. “No Ifs, Ands, or Butts” (Season 3, Episode 5)
On the one hand, this is the episode in which Carrie meets Aidan and goes on her first date with him. On the other hand, it plummets in our ranking for its clumsy handling of Samantha dating a black man named Chivon. Clichés abound, most notably his overbearing sister, and, worse, the show’s dedication to themes ends up equating Samantha and Chivon’s insurmountable racial differences with Aidan’s wish that Carrie quit smoking and Charlotte’s date’s lack of kissing skill. Let’s just say none of this would fly in 2018.
92. “Boy, Girl, Boy, Girl …” (Season 3, Episode 4)
Another one for the “times have changed” files: Carrie is all kinds of rattled to find out her hot young beau is bi. So much so that she runs out of a party, flustered, and not even in a good way, after sharing a brief smooch during spin-the-bottle with Alanis Morissette. Message received: No one’s going down on anyone in this theater.
91. “The Monogamists” (Season 1, Episode 7)
Aside from one important character development — turns out Mr. Big is still seeing other people, as Carrie discovers — there’s not much that’s memorable here.
90. “The Caste System” (Season 2, Episode 10)
A totally forgettable outing, with Miranda and Steve’s argument about money the only salient detail — and one that was already kinda apparent with the previous episode’s concerns about their differing schedules. And, um, Charlotte joins the entourage of a movie star named Wiley Ford? Sure. Whatever.
89. “The Awful Truth” (Season 2, Episode 2)
In what feels like a throwback to the first season’s piecemeal storytelling, Carrie gets drawn into her friend Susan Sharon’s clearly abusive relationship, Miranda dates a dirty talker, Charlotte gets a dog, and Samantha is in therapy with her less-than-endowed beau. We’re treading water while some much stronger second-season episodes are on the way.
88. “Four Women and a Funeral” (Season 2, Episode 5)
A vague potpourri of minor plots: Miranda buys an apartment and is single-shamed in the process, Charlotte meets a hot widower at a cemetery. Carrie also starts seeing Big again after their recent breakup, because of course she does.
87. “The Fuck Buddy” (Season 2, Episode 14)
Carrie explores a fuck-buddy relationship. Moving on.
86. “Games People Play” (Season 2, Episode 13)
Important(ish) takeaway this time: Carrie goes to therapy to deal with her Big issues, which, good idea. This is also the episode where she dates Jon Bon Jovi, a fellow patient, which, not a good idea. Moving on.
85. “La Douleur Exquise!” (Season 2, Episode 12)
Important takeaway: Big tells Carrie he’s moving to Paris for seven months. Other than that, we’ve got Miranda dating an exhibitionist, Charlotte dating a foot fetishist, and Samantha repping a new S&M-themed restaurant. Moving on.
84. “The Cheating Curve” (Season 2, Episode 6)
Plenty for the memorable moments reel here: Charlotte hanging out with “power lesbians” until they eject her from their clique by saying, “If you’re not going to eat pussy, you’re not a dyke.” Samantha’s trainer/lover shaving her pubic hair into the shape of a lightning bolt. Carrie’s stuck diaphragm being rescued by Samantha. It just doesn’t come together for the emotional impact of Sex and the City’s best.
83. “The Cold War” (Season 6, Episode 17)
A late-in-the-series placeholder. Aleksandr is already acting kind-of like a dick, not wanting to talk to Carrie about his work or introduce her to his friends. Samantha makes a sex tape with Smith to disprove tabloid reports that she’s his “fag hag.”
82. “Old Dogs, New Dicks” (Season 2, Episode 9)
A grab-bag of Sex and the City issues: Big keeps checking out other women while with Carrie (quelle surprise!), Miranda and Steve struggle against their opposite work schedules, Charlotte is chagrined to find her current beau is uncircumcised, and Samantha runs into an ex-boyfriend who’s now a drag queen named Samantha. That last one bumps this episode up a few notches.
81. “Bay of Married Pigs” (Season 1, Episode 3)
This episode coins the term “the marrying guy,” for, well, a guy who wants to get married so much that he barely seems to care who his bride might be. It’s a relatable situation for any single woman — sure, I might want to settle down, but not that badly. However, it’s not as memorable as other early episodes.
80. “The Power of Female Sex” (Season 1, Episode 5)
Carrie is mistaken for a high-class hooker — or something like that — when she beds a French architect and he leaves $1,000 on the nightstand for her. Meanwhile, Charlotte poses for a vagina painting by a famous artist. Both titillating, memorable situations for our heroines, but this one doesn’t do much to develop character or plot.
79. “Models and Mortals” (Season 1, Episode 2)
Sex and the City has its first major catchphrase moment with the term “modelizer,” which refers to a man who dates only models, which is hopefully not that useful in most of our real lives. We learn about this phenomenon when some jerk takes time out of modelizing to drag Miranda as his date to a dinner party, just so all of his friends get off his case about his modelizing ways. Turns out a friend of Carrie’s is also a modelizer, but he does it for the art: He tapes himself having sex with these glamazons for a video installation. This is some pure early Sex and the City, presenting an absurd exaggeration of a very tiny corner of Manhattan lifestyle so the rest of the country can feel sorry for us while simultaneously being kind of jealous.
78. “The Turtle and the Hare” (Season 1, Episode 9)
Unremarkable except for one major plot point: Charlotte gets addicted to the Rabbit vibrator! The episode made women’s masturbation seem, you know, as totally normal as it is, and also launched a Rabbit craze. There’s also some business where Carrie considers marrying her gay friend Stanford so he can get his inheritance and Samantha tries to help a wealthy, schlumpy bachelor known as The Turtle.
77. “Three’s a Crowd” (Season 1, Episode 8)
If you’re into early Sex and the City’s Socratic-dialogue approach to sex acts, this one’s for you. Carrie learns that Big once had a threesome with his ex-wife, Charlotte’s boyfriend wants a threesome, Samantha decides not to have a threesome with her married lover and his wife, and Miranda feels left out because she’s not “threesome material.” Viewers outside of Manhattan could be forgiven for thinking that all New Yorkers ever do is contemplate trio-based sex, but if you can suspend your disbelief, this all makes for an air-tight episode.
76. “Cock-a-Doodle-Do!” (Season 3, Episode 18)
Man, this is a weird one. On the one hand, Miranda’s Chinese takeout delivery woman seeming to mock her singlehood and Charlotte’s sexual reconciliation with Trey are gold. Carrie being awoken by a crowing rooster in the middle of Manhattan is also pure New York craziness. Even Samantha’s feud with her neighborhood’s trans prostitutes has its sweet moments when she and her friends find ample common ground with her nemeses. But after the recent revolution in how trans people are portrayed … let’s just say it’s no Transparent.
75. “The Freak Show” (Season 2, Episode 3)
Carrie ends up looking like a freak when she digs through a date’s stuff in an attempt to discover his secret freakishness, another great example of the show’s ability to undercut its heroine’s glamour with humiliation. Meanwhile, Charlotte continues to attract the guys with the most watercooler-worthy sexual predilections, this time dating the man known as “Mr. Pussy”; she, of course, hopes to move beyond his special skill and into a real relationship. You can guess how well that goes. A solid episode, though void of any real plot development or emotion.
74. “Shortcomings” (Season 2, Episode 15)
Not as meaty as some other episodes, but a fully realized Carrie plotline saves it, with a strong assist from two great guest stars — Justin Theroux (in his second appearance, after playing a totally different Carrie paramour) and the legendary Valerie Harper as his mom. In this case, poor Theroux’s character has a premature ejaculation problem that would be grounds for breakup … if Carrie didn’t love his mom so much. Given that she’s Rhoda Morgenstern, this makes sense. This episode is also notable for introducing Charlotte’s brother Wesley, whom we will never see nor hear about again.
73. “Was It Good for You?” (Season 2, Episode 16)
Carrie dates a recovering alcoholic, a gay male couple asks Samantha to have a threesome, and … oh, who are we kidding? This is the episode where the four women go to a sex seminar and Miranda gets hit in the face with flying ejaculate. Nothing else matters.
72. “The Baby Shower” (Season 1, Episode 10)
The gals head out to the suburbs for the dreaded baby shower of a once-fun city friend now lost to the haze of motherhood. Each goes through the motions you’d expect: Carrie has a mini-panic about motherhood when her period is late, Miranda scoffs at the suburbanites, Charlotte envies them, and Samantha throws a “no-baby shower” back in the city. It’s not much for plot development, but for single city ladies, it’s relatable AF.
71. “The Agony and the Ex-tacy” (Season 4, Episode 1)
Nobody shows up to Carrie’s birthday party, which is maybe enough punishment for that whole Big affair? Anyway, it’s pretty sad. Charlotte tries to get over the failure of her marriage, and Samantha tries (and fails) to seduce a priest she calls Friar Fuck. In conclusion, Charlotte suggests that the four friends could be each other’s soulmates, instead of men. Awww.
70. “Drama Queens” (Season 3, Episode 7)
Carrie declines to meet Aidan’s visiting parents, claiming that it’s too soon, because of course she does. (This is the woman who stalked Big and his mother at church in season one.) Charlotte steals this episode with her new, business-like approach to dating, hounding her friend’s husband into setting her up with his friend — only to find out that the husband has the hots for her. At the end, she gets her life-changing meet-cute when she almost gets hit by a cab and is rescued by one Dr. Trey MacDougal.
69. “The Drought” (Season 1, Episode 11)
Carrie obsesses over the consequences of having farted while in bed with Big, while Charlotte dates a guy whose antidepressant has squelched his interest in sex and Miranda realizes she hasn’t had sex in months. It’s a slightly subtler form of Sex and the City’s everyone-coincidentally-has-the-same-sex-hangup-at-the-same-time formula, and it works this time: Farting in bed is something a normal woman worries about in a new relationship, even if it’s not as shockingly memorable as a vibrator addiction or a modelizer epidemic.
68. “Secret Sex” (Season 1, Episode 6)
Carrie’s insecurity about Big is evident from the very beginning of their relationship, as on display here when she suspects that she’s his “secret sex,” a partner he’s hiding from his friends. This one sticks — we’re all afraid of being someone’s “secret sex” — and it reveals a key conflict that will drive the rest of the series.
67. “Valley of the Twentysomething Guys” (Season 1, Episode 4)
Carrie’s fling with a younger guy — played by the delicious Timothy Olyphant — establishes a welcome Sex and the City hallmark: dates that look better in theory than they are in practice. The show gets away with its glamorization of Manhattan single life largely by undercutting its heroines whenever they get too sure of themselves. Here, Carrie indulges a fantasy, only to wake up the next morning in a filthy apartment filled with the slobbery of multiple male roommates and no damn toilet paper. The secondary plot is also legendary: Charlotte debates the pros and cons of giving in to her beau’s request for anal sex and becoming “Mrs. Up-the-Butt.” The show is starting to find its groove here.
66. “Politically Erect” (Season 3, Episode 2)
Sex and the City is firing on all cylinders at this point, so even a mostly silly episode works thanks to tight construction. Carrie dabbles in Jackie Kennedy fantasies while dating John Slattery’s politician — until she discovers he has a pee fetish. (Hmm, prescient?) Try not to notice the conversation about how Carrie isn’t even registered to vote — different times, people!
65. “Are We Sluts?” (Season 3, Episode 6)
Posing perhaps the central question of the series — and leaving the answer to the viewer — this episode has Carrie confused when new beau Aidan wants to take things slow, Miranda humiliated when she has to call her past lovers to tell them she has chlamydia, Charlotte horrified when her lover calls her dirty names in bed, and Samantha incensed when her neighbors blame her late-night visitors for a robbery in the building. Nothing earth-shaking, but totally on point.
64. “Frenemies” (Season 3, Episode 16)
Memorable mainly for Carrie’s disastrous attempt to teach a “How to Find Love” class at the Learning Annex.
63. “Defining Moments” (Season 4, Episode 3)
Carrie goes on a friendly non-date with Big, where she strikes up a flirtation with a jazz musician, Miranda dates a guy who likes to take loud shits with the bathroom door open, Charlotte and Trey reconcile sexually, and Samantha meets a lesbian artist named Maria who makes her question her own sexuality. In all, a decent grab bag of mid-season Sex and the City action.
62. “What’s Sex Got to Do With It?” (Season 4, Episode 4)
The “Jazzman” Carrie’s dating turns out to have an annoying case of ADHD, even though he’s great in bed; Samantha announces that she’s dating a woman, an artist named Maria. Miranda substitutes chocolate for sex until she hits rock bottom when she finds herself pulling chocolate cake out of the garbage. It’s funny how the chocolate cake part is probably the image that lingers most from this episode, since Samantha’s gay relationship was never fleshed out enough to be believable.
61. “Ghost Town” (Season 4, Episode 5)
Aidan and Steve are back in Carrie and Miranda’s lives when the boys open a bar together and invite the girls, which helps amp up the drama here. Charlotte clashes with Trey’s mother, Bunny, as she moves back in with Trey and decides to redecorate. And this is also a wrap on Samantha’s relationship with Maria, who isn’t keen on the very long list of Samantha’s male exes.
60. “Sex and Another City” (Season 3, Episode 14)
More L.A. fun, including a jaunt to the Playboy Mansion.
59. “Escape from New York” (Season 3, Episode 13)
A much-needed burst of pure fun after the drama-heavy run of Big Affair and Charlotte Wedding episodes: The ladies go to Los Angeles, and bicoastal hijinks ensue! Lots of meta Hollywood stuff with Matthew McConaughey playing himself as interested in optioning Carrie’s columns for a movie. And Samantha meets a dildo model, because why wouldn’t she?
58. “Hot Child in the City” (Season 3, Episode 15)
A throwaway in terms of major plot points, but fun nonetheless: The real standout is guest star Kat Dennings as Jenny, a sexually precocious teen who hires Samantha to plan her million-dollar bat mitzvah. Samantha gives Jenny an unexpected lecture: “Ladies, aren’t you a little young for that kind of talk?” she says when she overhears them having a conversation worthy of Sex and the City brunch. “I’m serious. You have your whole lives to talk that way.” Who knew Samantha had a smidge of maternal instinct?
57. “Baby, Talk Is Cheap” (Season 4, Episode 6)
Carrie and Aidan get back together. What could possibly go wrong? Charlotte and Trey start their ill-fated attempt to conceive. Samantha wears fake nipples.
56. “Take Me Out to the Ballgame” (Season 2, Episode 1)
The show returns for its second season with swagger, building a just-plain-fun episode around the ladies attending a Yankees game — sunglasses, fur coats, heels, and all. They ogle baseball players in the locker room, make a lot of ball puns, and go meta with Miranda complaining about how much they talk about men. Sex and the City has arrived, bitches.
55. “Oh Come All Ye Faithful” (Season 1, Episode 12)
Carrie faces the fact that Big might not be in it for the long haul when he introduces her to his mother as “a friend.” Granted, this is just after she has crashed his mother-son church visit while wearing one of the series’ first memorable outfits, a green-and-white-striped, vintage-style dress, a wide-brimmed hat, and white gloves (!). Meanwhile, Samantha finds an otherwise-perfect guy whose penis doesn’t measure up, and Miranda contends with a Catholic playwright who insists on showering immediately after sex. This first-season finale nails down the Sex and the City formula and vibe just in time to lure us back for season two. It’s confident, relaxed, heartbreaking, and funny without trying as hard as some other first-season episodes.
54. “Sex and the City” (Season 1, Episode 1)
The show’s central thesis is writ large: At a birthday gathering for Miranda, the four women vow to stop worrying about finding Mr. Right and instead to have “sex like men,” without commitment or emotion. Carrie does exactly that, hopping into bed with an ex-lover and getting her cunnilingus to go — without returning the favor. But that overarching narrative is cleverly undercut when she keeps bumping into a mysterious guy she calls Mr. Big, romantic encounters that scream “fate.” It’s trying a bit too hard, but so are most pilot episodes, so it’s easy to forgive. Carrie’s direct address to the camera, less easy.
53. “Evolution” (Season 2, Episode 11)
Another of the solid second-season episodes that help the show transition from freaky-sex-of-the-week to soul-stirring meditation on life, love, and friendship in your thirties and beyond. Carrie persists in her frustrating attempts to turn Big into a committed boyfriend, leaving stuff at his place only to have it returned. Miranda, meanwhile, finds out that one of her ovaries is no longer working. The week’s watercooler fuel comes courtesy of Charlotte, who ends up dating a pastry chef she thought was gay, and is delighted to learn is straight. He calls himself a “gay straight man.” A few years later we’d call him a metrosexual, and now we’d call him a man who identifies as straight and also enjoys baking.
52. “Just Say Yes” (Season 4, Episode 12)
Aidan proposes and Carrie says yes, even though all signs point to “no.” Charlotte proposes adoption to Trey, but Bunny objects, because she’s racist and doesn’t want a Chinese grandchild. Miranda tells Steve she’s pregnant with his child, and Samantha starts dating her client, Richard Wright. It’s a solid note to end what was technically the midpoint of the fourth season, but the last episode before a five-month hiatus during which 9/11 would happen.
51. “Cover Girl” (Season 5, Episode 4)
Carrie (rightly) freaks out when she learns that her publisher wants to use a nearly naked photo of her on the cover of her book — so she enlists publicist Samantha to help. This leads to a pretty interesting conflict as they clash over what’s tasteful versus trashy; and that clash is compounded when Carrie walks in on Samantha blowing a Worldwide Express delivery guy and flees in horror. Samantha rightfully feels judged, and they’re forced to hash out their differences.
50. “The Big Time” (Season 3, Episode 8)
Carrie runs into the now-married Big, who tells her he misses her, kicking off a love square — his wife, her boyfriend Aidan — that will make for a string of riveting episodes. Charlotte’s in fine form as she swoons over her WASPy new love, Trey, and Samantha panics that she’s entering menopause when her period is a week late. The only weakness here is Miranda’s irritation with Steve’s childishness, which is overdone by at least half. The guy who worked his way past Miranda’s tough defenses suddenly can’t turn Scooby-Doo off to have a serious conversation?
49. “Luck Be an Old Lady” (Season 5, Episode 3)
That old Sex and the City levity finally makes a major appearance in what had so far been a subdued post-9/11 season. The four women head to Atlantic City to celebrate Charlotte’s birthday, and while it’s not the most significant episode, it does feature Charlotte in a wonderfully vampy, skin-tight dress (impending Midlife Crisis?) and a great bit where the women tell off a casino guy who disparages Miranda’s “fat ass.” Miranda: “My ass is fat because I just had a baby, you asshole!” Samantha: “What’s your excuse?” Carrie: “Yeah, ya havin’ triplets?”
48. “Let There Be Light” (Season 6, Episode 13)
Things are unsettled as we head into the show’s final stretch: Miranda and Steve are now together, but they keep bumping into her ex, Dr. Robert Leeds, who lives in her building and is understandably displeased with how things turned out. (He’s basically like, “Don’t you know I am played by Blair fucking Underwood?”) Samantha cheats on Smith almost literally in front of him at a party, heading upstairs with her ex Richard for a quickie. Smith, being the most perfect boyfriend in Sex and the City history, forgives her and they forge ahead with their relationship.
47. “All That Glitters” (Season 4, Episode 14)
The melancholy mood of this part of the season continues as Charlotte and Trey separate for good after being photographed in their apartment together for House & Garden. Samantha uses the L-word on Richard, but it’s while she’s high on ecstasy. All clues continue to point away from a wedding for Aidan and Carrie: This time, Carrie escapes home life by going clubbing with a hot, gay Australian shoe distributor.
46. “One” (Season 6, Episode 12)
Carrie meets Russian artist Aleksandr Petrovsky at a gallery; he is instantly intriguing because he is played by legend Mikhail Baryshnikov, whose small stature belies his intense gravity on screen. Poor Dr. Robert Leeds gives Miranda a cookie that says “I Love You,” but she goes and declares her love to Steve instead. Charlotte miscarries, and Samantha dyes her bush, which is if nothing else an indication of the show’s impressive ability to toggle moods.
45. “The Domino Effect” (Season 6, Episode 11)
Big needs heart surgery (insert metaphor of your choice here), prompting Carrie to have an emotional breakdown and dress up like a candy striper to visit him. In another gigantic metaphor with medical implications, Samantha falls into an open sidewalk cellar door to avoid holding Smith’s hand. It’s pretty funny, really, and will give you a fear of those damn hatches for eternity.
44. “Boy, Interrupted” (Season 6, Episode 10)
Notable for Miranda starting her relationship with Dr. Robert Leeds, played by Blair Underwood. This is also the one where Samantha pretends to be a random British lady to get into the pool at SoHo House.
43. “The Perfect Present” (Season 6, Episode 3)
Things continue along: Carrie worries that Berger’s still a little too angry with his ex to be ready for a new relationship, Miranda gets mad/jealous when she finds that Steve left condoms in Brady’s diaper bag, Charlotte converts and mourns for Christmas.
42. “To Market, to Market” (Season 6, Episode 1)
Carrie obsesses in anticipation of her first date with Berger and runs into Aidan, who now has a child. Miranda, meanwhile, realizes she’s in love with Steve, but he has a new girlfriend, and Harry tells Charlotte he can’t marry her because she’s not Jewish. A perfectly solid start to the final season, with intriguing threads to follow until the end.
41. “Great Sexpectations” (Season 6, Episode 2)
Carrie and Berger flame out in the bedroom — so badly that at one point they can hear the bus pull up, open its doors, close them, and drive off. Miranda gets hooked on TiVo, specifically a British soap opera about an interracial couple called Jules and Mimi, and Charlotte looks into converting to Judaism for Harry. Extra points for this being the first appearance of delicious young waiter/actor/model/Samantha-love Smith Jerrod (né Jerry Jerrod).
40. “I Love a Charade” (Season 5, Episode 8)
The ladies head to the Hamptons to attend the wedding of a lounge singer they thought was gay to a socialite named Bitsy von Muffling. The setting allows for a fun season finale as Carrie runs into Berger again, Samantha throws a party at Richard’s house, and Charlotte goes public with her relationship with Harry Goldenblatt. Yay for Harry Goldenblatt! The underlying message, however, is downright existential: Even as Carrie waxes poetic about finding “zsa zsa zsu,” the wedding sends the message that maybe soul-shattering love isn’t the answer after all. Maybe companionship is what we need most in the end.
39. “Critical Condition” (Season 5, Episode 6)
Carrie’s book gets a great New York Times review, allowing for a number of Michiko Kakutani references, but she can’t get over the “negative review” she gets from Nina Katz, who dated Aidan right after their breakup. Samantha does something truly heroic in her terms: She gives Miranda her hair appointment and watches new baby Brady so Miranda can go. And Charlotte trades in her hot divorce lawyer for his less overtly hot partner, Harry Goldenblatt … yay, Harry Goldenblatt!
38. “Plus One Is the Loneliest Number” (Season 5, Episode 5)
Carrie’s book is out, so naturally Samantha throws her an epic book party resembling very few real book parties ever. But this does allow for a magnificent gag about Samantha having to show up despite a terrible chemical peel, and it also allows Carrie to invite her new flirtation, novelist Jack Berger. Alas, he has a girlfriend.
37. “The Big Journey” (Season 5, Episode 7)
Good on a sheer hijinks level, this episode has Carrie and Samantha crossing the country on a train to get to a book tour stop in San Francisco for Carrie — and, yes, so she can sleep with Big while she’s in the neighborhood. Big got her a plane ticket for just such an occasion, but she makes a rare overt 9/11 reference in defending her train choice: “I get uneasy seeing the National Guard go through my makeup case.” The women dream of a glamorous old-timey train journey, but instead they get cramped quarters even in the deluxe, first-class sleeper; a bachelor party full of loyal married guys; and a giant zit for Carrie. “I’m starting to understand why there was a murder on the Orient Express,” Samantha quips. Once they get there, Carrie almost doesn’t get her sex reward, so concerned is Big with the way he’s portrayed in her book. The better news: Charlotte sleeps with her sweaty, crude divorce lawyer, Harry Goldenblatt, and has great sex. Yay, Harry Goldenblatt!
36. “The Good Fight” (Season 4, Episode 13)
The first Sex and the City episode to air after 9/11 doesn’t acknowledge the tragedy except for a minor edit in the credits — because it was shot during the months just before. But it’s pretty damn good anyway (and has an appropriately unsettled mood), particularly the epic fight Aidan and Carrie have over closet space. (Carrie: “Don’t mock the clothes.”) There’s also a hilarious/heartbreaking bit where Trey tries to cheer Charlotte up about their infertility … by giving her a cardboard baby.
35. “Coulda, Woulda, Shoulda” (Season 4, Episode 11)
Significant as the rare U.S. television episode to depict a main character seriously considering abortion; also significant in that another main character admits to having had an abortion years ago. In this case, we’re talking Miranda, whose cancer-surgery sex with Steve apparently led to conception, and Carrie, who is moved to ponder her own abortion when she was 22. To make matters more poignant, Charlotte discovers she has only a 15 percent chance of getting pregnant herself. Somehow there’s still room for a little comedy, too, with Samantha using her new client, Lucy Liu, to score a Birkin bag.
34. “Belles of the Balls” (Season 4, Episode 10)
Turns out the only thing funnier than Carrie in the country house with Aidan is Big and Carrie in the country house with Aidan. Big comes up seeking company after his breakup with the movie star, and Aidan is a real gem for most of the awkward encounter. But male aggression eventually gets the best of both of them, and they end up wrestling in the mud. Other significant developments include Miranda sleeping with Steve to cheer him up after having a testicle removed, Charlotte and Trey struggling with infertility, and Samantha courting hotelier Richard Wright — as a client.
33. “Sex and the Country” (Season 4, Episode 9)
Carrie tries to live a bit more of the Aidan lifestyle by spending time with him at his fixer-upper cabin in the appropriately named Suffern, New York. It’s a great setup for City Mouse gags like Carrie’s massive overreaction to a squirrel ruining her attempt to bake a pie. And yes, don’t worry, Samantha joins them for just enough time for a roll in the hay with “Young MacDonald” next door. The differences between Aidan and Carrie, however, also hold larger significance: Carrie briefly flees back to the city for a “friendly” dinner with Big, who tells her he’s dating a movie star. And we already see that Aidan and Carrie are not cut out for each other over the long run. Steve also tells Miranda he has testicular cancer, a major turning point in their relationship.
32. “Lights, Camera, Relationship!” (Season 6, Episode 5)
A fatal fissure appears in Berger and Carrie’s relationship when she gets a big royalty check and his second novel is rejected. The situation is exacerbated when Carrie is treated like a celebrity at the glitzy opening for Smith’s play that Samantha has organized. It’s a memorable depiction of one of Sex and the City’s most interesting relationship issues: what happens when a woman is more successful than the man she loves.
31. “Time and Punishment” (Season 4, Episode 7)
Big leaves a message for Carrie while she’s having sex with Aidan, an excellent argument for the coming advent of iPhones. (Also, not a great sign of things to come.) Charlotte decides to leave her job at the art gallery to pursue motherhood full-time, prompting one of the series’ clearest feminist debates: All three other women disapprove, Miranda most of all, but Charlotte insists that the women’s movement gave her the right to opt out of work. “I choose my choice!” she insists, fueling think pieces for years to come.
30. “The Catch” (Season 6, Episode 8)
Charlotte and Harry get married!
29. “Hop, Skip, and a Week” (Season 6, Episode 6)
After Charlotte and Harry break up, she becomes a hot commodity on the Jewish singles scene. But they soon realize they belong together … and Charlotte is engaged again! Meanwhile, Samantha gets Smith a super-hot Absolut ad in Times Square. Berger also tells Carrie he needs “a break” from the relationship, which is never a good sign.
28. “The Real Me” (Season 4, Episode 2)
Carrie walks the runway — in some very memorable sparkly underwear — and takes a spill, becoming “fashion roadkill.” Charlotte struggles with a “depressed vagina,” a.k.a. vulvodynia, and works it out thanks to some ‘70s-style hand-mirror action. Samantha gets boudoir shots done, and Miranda has to embrace her confident side when a fit guy from the gym asks her out. One of Sex and the City’s most unapologetically empowering outings, even with the runway spill to keep Carrie grounded.
27. “Twenty-Something Girls vs. Thirty-Something Women” (Season 2, Episode 17)
Our four thirty-something women head to the Hamptons, where Carrie runs into Big — who’s back from Paris with a new 27-year-old girlfriend, Natasha. Thus Carrie’s push-and-pull with Big comes to a head (for the first of several times), and the show becomes the gripping combination of soap opera, comedy, and affecting drama we’ll truly get addicted to.
26. “What Goes Around Comes Around” (Season 3, Episode 17)
After a break full of frivolous episodes, we return to the heavier relationship drama from earlier in the third season as Carrie decides she needs to talk to Big’s ex-wife Natasha to clear the air about the affair. Well, first there’s a pretty funny scene in which Carrie is mugged … in the middle of the day … in SoHo … by an assailant who asks for her Manolos by name. Then she decides it’s her bad karma following her. The confrontation is a fantastically surprising moment in which the heretofore underestimated Natasha puts our heroine in her place. It might be the first time we truly realize that Carrie is deeply flawed, and redemption is not a sure thing. Charlotte and Trey also make the heartbreaking decision to separate.
25. “Ex and the City” (Season 2, Episode 18)
The season-two finale brings it home with parallels to the season-one finale, coupled with a more assured vision this time around. The last scene, in which Carrie sends Big off to his young, new fiancée, is a killer, just like the romantic car ride she and Big share at the end of the first season. Samantha even ends up with a guy whose equipment is too big, instead of Mr. Too Small from season one, leaving us to wonder if she’ll ever find Mr. Just Right. (Or, later, Mr. Richard Wright.) Miranda has more great rom-com material as she tries to be “just friends” with Steve, but fails.
24. “A Vogue Idea” (Season 4, Episode 17)
Sex and the City’s only #MeToo moment came courtesy of Ron Rifkin as Vogue editor Julian, dropping his drawers on Carrie in the magazine’s hallowed fashion closet. Nothing much comes of it except for Carrie’s commitment to instead working with the divine editrix Enid, played by Candice Bergen — a welcome older, wiser female presence for several episodes.
23. “Out of the Frying Pan” (Season 6, Episode 16)
Miranda moves to … Brooklyn! How will anyone ever see her anymore? Do they even have trains there? How about cable and running water? The truly indelible image from this episode is Samantha shaving her head as her chemo progresses, and Smith doing the same in solidarity. And obviously he looks great without hair. Most. Perfect. Boyfriend. Ever.
22. “Unoriginal Sin” (Season 5, Episode 2)
This is the calm after some major storms, from 9/11 in the real world to the plot upheavals of the show’s most dramatic breakups so far — Carrie and Aidan, Samantha and Richard, Charlotte and Trey. But it’s fortifying to see the women start to pull themselves together again, particularly Charlotte, who dives into a self-help seminar to help her find love again — the woman’s optimism is startling. So much so that Carrie is moved to tell the dating-guru instructor and her room full of acolytes what an inspiration her romantic friend is. It’s shockingly moving when, after the guru tells Charlotte to put herself out there, Carrie says, “Believe me. She’s out there.” And in another surprising act of faith, Samantha takes Richard back, despite his cheating. Oh, also! Carrie gets a book deal!
21. “Where There’s Smoke …” (Season 3, Episode 1)
Now we’re getting into prime Sex and the City territory. You know it’s going to be good the minute the four women get on the Staten Island Ferry to head to a hot-fireman contest. It only gets better when the delicious John Slattery shows up as a local politician — and Carrie’s fellow judge and sexy suitor. Charlotte declares herself ready to get married within a year, Samantha has a graphic romp with a fireman at the firehouse, and Miranda gets LASIK eye surgery, which gifts the world with this image.
20. “Ring a Ding Ding” (Season 4, Episode 16)
Otherwise known as the episode in which we learn Carrie has spent roughly $40,000 on shoes in her lifetime but has very little savings, this installment has Carrie pondering how to buy back her condo-ized apartment from Aidan after their breakup. Big offers to lend her the money, but in one of her few reasonable decisions involving him, she doesn’t end up taking it. Instead, Charlotte offers her Tiffany engagement ring as a financing tool. It’s a hotly debated plot point — and, yes, it’s obnoxious that Carrie nearly demands Charlotte help her out — but it underlines the series’ main tenet: that friends can be family. Even if one of them is kind of gross about it.
19. “Catch-38” (Season 6, Episode 15)
Carrie faces a choice rarely depicted on TV: As she gets more serious with her older Russian suitor Aleksandr, she finds out he doesn’t want any more children. At age 38, she’ll have to think carefully about how much time she invests in the relationship. Carrie, eating a black-and-white cookie: “I’m running out of time. I don’t even have time to eat this cookie.” Charlotte: “How is it?” Carrie: “It’s so good I forgot to have children.” She stays with the Russian, setting up the finale.
18. “Splat!” (Season 6, Episode 18)
Kristen Johnson, playing one of the gals’ old party friends, falls out a window after declaring, “I’m so bored I could die.” Jolted by this and Petrovsky’s announcement that he’s moving to Paris, Carrie decides to go with him. The die is cast for our final episodes.
17. “The Post-It Always Sticks Twice” (Season 6, Episode 7)
Yeah, it’s the Post-It break-up read round the world. Berger’s still somewhere trying to live that down.
16. “Pick-a-Little, Talk-a-Little” (Season 6, Episode 4)
Famous for the “he’s just not that into you” line, this episode also packs the first major emotional wallop of the sixth season. In a gorgeous sequence, a newly converted Charlotte cooks her first Shabbat dinner for Harry, but he just wants to watch a baseball game — a conflict that leads to their breakup. This is also the installment in which Carrie criticizes new writer-beau Berger’s use of a scrunchie to accessorize a woman in his novel who is supposed to be a sophisticated New Yorker. Don’t tell Carrie that scrunchies are now back, on the heads of sophisticated millennials everywhere.
15. “A Woman’s Right to Shoes” (Season 6, Episode 9)
One of several final-season episodes that instantly sparked a trend: In this case, single women registering for gifts to celebrate their independence. This comes after Carrie loses her Manolos at her friend Kyra’s baby shower, at which Kyra insists guests go shoe-free. Carrie demands compensation, but Kyra balks at the $485 price tag and adds a serious dose of mommy judgment. In the end, Carrie registers for her wedding … to herself! She informs Kyra that the registry is at Manolo Blahnik, and there is one item on it. She gets the shoes.
14. “All or Nothing” (Season 3, Episode 10)
Another in this string of exquisite mid-season-three episodes, this one includes the classic sequence in which Carrie loses Aidan’s dog in the rain when Big comes to tell her he wants to be with her. (And, not for nothing, she sprints down the street in stilettos and shorts.) Aidan later tells her he’s suspicious — that she’s smoking again. The addiction metaphor is clear. Charlotte continues her character’s evolution by playing hardball with Trey’s mother, Bunny, over the “standard” MacDougal family prenuptial agreement. (This will later be critical.) For our extra pleasure, Miranda enjoys a phone sex relationship with a colleague from Chicago and Samantha reconsiders her commitment to singlehood when she gets the flu.
13. “Easy Come, Easy Go” (Season 3, Episode 9)
Big tells Carrie he’s leaving his wife, while Miranda and Steve break up but are forced to keep living together as he looks for a new place. But it’s Charlotte’s story that shines like a Tiffany engagement ring: After observing how Trey’s mother manipulates him into doing what she says, Charlotte similarly suggests they get married. His answer: “Alrighty.” The WASP princess will become a queen, but without the proposal she’s dreamed of her whole life. As a bonus weird-sex story, Samantha dates the guy with “funky spunk.” It’s another perfect Sex and the City half-hour.
12. “They Shoot Single People, Don’t They?” (Season 2, Episode 4)
Carrie agrees to a photo shoot for a New York magazine cover story she believes is to be headlined “Single and Fabulous.” Instead her test shot, cigarette dangling, makeup-free face glaring, ends up on the cover under the headline “Single and Fabulous?” It’s a hilarious commentary on media trend stories about single women, a typically perfect humiliation of our media-darling heroine, and a great excuse for her to almost hook up with a young Bradley Cooper in one of his first roles. Such a pitch-perfect episode, we’ll forgive the New York dig.
11. “The Chicken Dance” (Season 2, Episode 6)
Sex and the City becomes its best self in this episode, shifting from the parade of dudes with sexual predilections to a soulful, serialized show about four very different women leaning on each other as they figure out life and love. The action centers on the super-fast courtship and wedding between Miranda’s interior decorator and a guy Miranda had hoped to woo for herself. The emotional kick comes when Carrie, still desperate for a sign that Big is serious about their relationship, sees him take a phone call during her reading of a love poem at the reception. This tortuous — but riveting and all too relatable — emotional dynamic will drive the rest of the series.
10. “Running With Scissors” (Season 3, Episode 11)
In which the Big-Carrie affair hits rock bottom. Big’s wife, Natasha, catches Carrie in their apartment, chases her out, and on the way falls down the stairs and cracks a tooth. Carrie takes Natasha to the hospital, where she also tells Big they’re “so over they need a new word for over.” (Ha, if only.) Charlotte, hitting bridezilla mode, hires stylist Anthony Marentino, thus introducing a new recurring character and nemesis for Carrie’s friend Stanford. Samantha’s storyline brings the standard kink — she meets the “male version” of herself, a storied sex god who has a leather sex swing in his apartment. But she also gets an unexpected emotional jolt when he asks her to take an HIV test, which she’s never done because she’s terrified.
9. “The Man, the Myth, the Viagra” (Season 2, Episode 7)
We’ll ignore Donald Trump’s clunky cameo and focus on the tearjerking ending. Big continues to be infuriatingly ambivalent about his relationship with Carrie … until he shows up, despite pouring rain, to meet her and her friends for dinner. And Miranda resists bartender Steve’s every sweet attempt at a real relationship after a one-night stand … until Big’s arrival shows her she was wrong about men, and she runs out into the rain to kiss Steve. Rain! It makes every rom-com better.
8. “The Attack of the 5’10” Woman” (Season 3, Episode 3)
This is the first perfect episode of Sex and the City, full stop. Carrie confronts Big’s new, young wife, Natasha, and it’s not a cute look for Carrie. Miranda does emotional battle with her new cleaning lady, Magda, who leaves her a Virgin Mary statue in her “goody drawer.” Charlotte deals with her body issues thanks to a sauna, and Samantha demands a happy ending from her masseur. Honestly, what more could you want? As classic as a little white tutu.
7. “An American Girl in Paris (Parts Une et Deux)” (Season 6, Episodes 19 and 20)
A lot of ink and pixels have been spilled on this series finale, and we’re not going to get into all of that here. We can debate the Big gesture and grand romantic ending until the end of time, and we’re never going to change the fact that this finale chooses Big + Carrie 4-eva (or until he bails on their wedding, or whatever other shenanigans he gets up to in their fictional future away from the cameras). The fact that it still inspires passionate debate speaks to its power, and to the power of the series as a whole. This two-parter also happens to be gorgeously shot, perfectly plotted, sumptuously costumed, and very satisfying to millions of fans. So if we’re ranking episodes, this has to be high up for its technical prowess and its memorability, even if better episodes throughout the series made bolder and clearer statements about Carrie’s relationships with her friends and her city — two loves that no grand gesture will ever overshadow. As Big says to the other women before he heads to Paris, “You three know her better than anyone, you’re the loves of her life. And a guy’s just lucky to come in fourth.” Don’t you forget it, buddy.
6. “Anchors Away” (Season 5, Episode 1)
Sex and the City handled 9/11 with dignity and class, showing its genuine love for the city with several subtle episodes after the tragedy, most notably this one — the very first shot after September 2001. Without making a fuss, this episode pays homage to New York and patriotism, still allowing for the show’s sense of fun as the women party at Fleet Week with U.S. Navy men visiting for the annual tradition. In the end, however, Carrie has to defend her city to the gorgeous, Southern Navy boy she’s snagged, who just doesn’t get New York: “I can’t have nobody talking shit about my boyfriend,” she says as she saunters off.
5. “The Ick Factor” (Season 6, Episode 14)
In one of the show’s most emotional turns, Samantha finds out she has breast cancer when she goes in for a breast augmentation consult. Miranda and Steve have their low-key wedding, which Samantha tries not to ruin with her news. The truth emerges in a friendship moment for the ages during the reception. After Samantha tells Carrie and Charlotte, the three fall silent when Miranda approaches. Miranda begs to know what’s going on — “Forget about my special fucking day, just be normal.” Samantha blurts out that she has cancer. Charlotte tells Miranda, “Now go back to your people and we’ll talk about this later.” Miranda: “You are my people and we’ll talk about this now.” No sugar-coated wedding or cancer bullshit for these bitches. This episode is why so many of us love them.
4. “Change of a Dress” (Season 4, Episode 15)
Emotional devastation is Sex and the City’s strong suit, and here’s another case in point: Carrie breaks out into hives when she tries on a wedding dress, which, FYI, is never a good sign. This leads us to one of the show’s major tearjerkers, the scene by the Columbus Circle fountain when Aidan pushes Carrie to elope … and ends up pushing them to their fated breakup. “I can’t believe I’m back here again,” Aidan says. Same, Aidan. Same.
3. “Don’t Ask, Don’t Tell” (Season 3, Episode 12)
Charlotte marries Dr. Trey MacDougal in her dream wedding — dreamy, that is, except for the part where she finds out the night before that he’s impotent. Fun side notes include Miranda pretending she’s a stewardess instead of a lawyer to get a date, and Samantha sleeping with Trey’s cousin, whose Scottish accent renders him unintelligible to her. The devastation comes when Carrie finally reveals her affair with Big to her boyfriend Aidan. “Couldn’t it be like the wood?” Carrie says, desperately invoking a romantic metaphor he used earlier to describe a furniture piece he made as a wedding gift. “That’s my flaw, and you’re the other wood, and that makes us stronger.” It’s not that simple, he tells her. “This is not the kind of thing I can get over.”
2. “My Motherboard, My Self” (Season 4, Episode 8)
In this transcendent meditation on the ways we need and resist support, as well as on the meaning of family, Miranda’s mother dies and Carrie’s computer crashes. After Samantha hears the news about Miranda’s mom, she “loses” her orgasm, a nod to something darker beneath her surface — which we never totally unearth — as well as a hint at mortality. Carrie pushes Aidan away as he tries to help with her technical problems, but she rushes to Philadelphia with Charlotte and Samantha to be by Miranda’s side for the funeral. The scene when the women rush in to escort Miranda down the church aisle behind the casket is a tear-inducer for the ages.
1. “I Heart NY” (Season 4, Episode 18)
It’s nearly impossible to choose between this and “My Motherboard, My Self” as Sex and the City’s best, but this one perhaps gains a slight edge for its emotional resonance at the time: It was a wistful homage to the magic of New York City that aired five months after 9/11. It was exactly what we needed at the time. Plot-wise, Big announces he’s leaving Manhattan for Napa, and he and Carrie spend one last classic New York night together, carriage ride and all. She wears exquisite flouncy pink shoes. They dance to “Moon River” (which he has on vinyl, of course) in his nearly empty apartment. Then Miranda goes into labor, Carrie rushes to her side, and when she returns to his apartment in the morning, he’s gone. He’s left her a plane ticket to come visit him out west. It’s Big and Carrie at their best, it’s Carrie choosing her friend over Big when she needs to, and it’s New York at its finest.