The best Sex and the City episodes fall into one of two categories. There are those that provide joyful, carefree escapism: endless cosmopolitans, rent-controlled Upper East Side apartments, journalists who can afford Prada, and flings with guest stars ranging from Bradley Cooper to Vince Vaughn. Then there are those that grapple with the complicated (and often harsh) realities of being female in a patriarchal society: casual workplace sexism; tired ageist standards of beauty; the constant, never-ending pressure to settle down; and the omnipresent dilemma of whether or not to have children when everyone seems to expect you to. There were 93 in the drama’s original six-season run—some good, some bad, and some deeply ugly. With the recent arrival of And Just Like That… Season 2, here are the best SATC episodes to rewatch now.
“Valley of the Twenty-Something Guys”
This is a classic episode in which Carrie is seduced by a wannabe ’90s boy-band member, who flashes his tongue ring at her in a bar and happens to live in what I can only describe as a nuclear fall-out shelter decorated by Jerry Garcia. It’s also the point when Charlotte begins to reveal that she is, in fact, the worst. Her three priorities when dating, according to Carrie, are “looks, manners, money”—a romantic approach that somewhat backfires when her investment banker du jour requests she try anal sex after a few weeks of dating. Bonus points for the girls’ in-depth conversation about the power dynamics inherent in going “up the butt” in the back of a cab.—Hayley Maitland
“The Turtle and the Hare”
Another classic for a reason! Plenty goes on in this episode—Miranda tries blind dating; Samantha tries to Love It or List It a guy with potential (and bad breath); and Carrie meets Stanford’s very chic grandmother—but it’s all just a backdrop for the A story, which concerns Charlotte’s newfound appreciation for the Rabbit vibrator. This episode will go down in history for helping introduce a generation of women to sex toys.—Emma Specter
“The Baby Shower”
Nothing good happens when the Big 4 leave their natural habitat of Manhattan—aggressive bikini waxes in L.A., cultural faux pas in Paris, sexually transmitted diseases in the Hamptons, and don’t even get me started on Abu Dhabi. Their mishaps at a reformed party girl’s Connecticut home in “The Baby Shower,” however, are both hilarious and poignant—with each character weighing up her own feelings about motherhood. Also of note: Samantha and Miranda’s baby shower gifts: a bottle of scotch and pastel-colored condoms.—H.M.
“Take Me Out to the Ballgame”
Each main character is peak “herself” in this episode. Carrie agonizes over her relationship with Mr. Big—both in Manhattan (“a deserted battlefield, loaded with emotional landmines”), and at a Yankee game, where she asks a baseball player to the Dolce Gabbana party and strings together endless weird baseball metaphors about her romantic life. (“If I were a ball player, I’d be batting, uh, whatever really bad is.”) Miranda is personally victimized by the wardrobe department and thrilled about her PalmPilot; Charlotte attempts to solve a relationship problem with a Barneys purchase and literally zero communication; and Samantha uses various unsuspecting objects to demonstrate the size of her boyfriend’s penis.—H.M.
“They Shoot Single People, Don’t They?”
After staying out all night, a tequila-soaked Carrie has her portrait taken for the cover of New York’s “Single Fabulous” issue, only for the magazine to run with a photograph of her looking like “something that got caught in a drain” and a damning editorial (“How fun will all-night club hopping be at 40?”) that frightens all of the girls into crappy relationships. Samantha dates a salsa club owner; Charlotte begins sleeping with her “Mr. Fix-It” friend; and Miranda has terrible sex with an ophthalmologist. (Him: “I know all about women’s anatomy. I’m a doctor.” Her: “You’re an eye doctor.”) One of the series’s best depictions of the emotional contortions that (mostly female) people go through as a result of single-shaming bullshit.—H.M.
“Twenty-Something Girls vs. Thirty-Something Women”
God help me, I love an “away” episode, and this one nails the Hamptons mise-en-scène: boring book parties, sleazy time-shares, semi-ironic cowboy hats. Carrie and the gang get to feel superior to 20-something girls for approximately one second, until it transpires that Mr. Big is—gasp—dating one himself. Also, Samantha triumphs over her bratty assistant; Charlotte gets laid; and Miranda . . . stays out of the sun, which is good, I guess.—E.S.
“Ex and the City”
Even if you loathe Mr. Big (and occasionally Carrie), the final episode in Season 2 of Sex and the City is distinctly moving—particularly the moment when John tells his former girlfriend that he’s proposed to his current one (“the idiot stick figure with no soul”) over Cobb salads at Eleven Madison Park (pre-Daniel Humm’s takeover, obviously). In truly deluded—but weirdly endearing?—fashion, Carrie decides that their relationship failed because she’s a complicated girl, like Barbra Streisand in The Way We Were, and Big, like Robert Redford, ultimately chose a simple one (Natasha/“Nijinsky”). The fact that Carrie once creepily arranged a meeting with Big’s ex-wife and pitched her a children’s series titled Little Cathy and Her Magic Cigarettes is, strangely, never mentioned.—H.M.
“The Attack of the 5’10” Woman”
This episode largely centers on Carrie, who, after reading about Big and Natasha’s Hamptons wedding in the New York Times’s Style section, obsessively compares herself to the Ralph Lauren executive—dragging Samantha along to a Women in the Arts luncheon in the hopes of bumping into her nemesis. Far more importantly, this is the first Sex and the City episode featuring Miranda’s housekeeper and nanny Madga, who makes artful displays out of herbal tea bags and replaces Miranda’s vibrator with a Virgin Mary statuette. Miranda’s impeccable response: “I’m a 34-year-old, single woman living in New York. I drink coffee, have sex, buy pies, and enjoy battery-operated devices.”—H.M.
“Running With Scissors”
Miranda is often stuck with the more ridiculous story lines, and this one is no exception; she starts getting street-harassed by a guy in a promotional sandwich costume, for whom she eventually finds herself developing feelings, but sadly, it is not to be. “She was a lawyer, and he was a sandwich.” Were more iconic words ever spoken?—E.S.
“Don’t Ask, Don’t Tell”
“Don’t Ask, Don’t Tell” takes the fairytale Upper East Side wedding and turns it on its head, with Charlotte discovering Trey’s impotence problem on the eve of their nuptials. She decides to go through with the ceremony anyway (“Charlotte was 34, single, and standing in a $14,000 dress—she was getting married”). Meanwhile, true to selfless form, Carrie tells Aidan about her Big mistake on her best friend’s wedding day, then arrives late to the church. To quote Samantha, “Marriage doesn’t guarantee a happy ending, just an ending.”—H.M.
“Escape From New York”
It might be the antithesis of these New Yorkers’ lives, but how can you hate on an episode of Sex and the City in which a) Carrie meets with Matthew McConaughey and he yells at her, b) Samantha dates a dildo model, and c) Miranda rides a mechanical bull? Plus, nobody will let Carrie smoke! L.A. is anarchy!—E.S.
“Hot Child in the City”
This is a perfect (almost) bottle episode about the core feelings of youth: freedom, embarrassment, jealousy, and... horniness (that would be Trey, caught jerking off to Juggs magazine by a very shocked Charlotte). Samantha gets hired by a superrich 13-year-old who needs PR for her bat mitzvah, and Samantha spends the whole episode jealous of her until she realizes that she had something the teen girl doesn’t—a real childhood. (It’s a rare moment in which Sam is written with real, human emotions, rather than as sexual comic relief.) Carrie, meanwhile, starts dating Wade, a dude who owns a comic book store (played by Cane Peterson, who used to be a VJ on VH1, a sentence that no one has uttered in decades, probably). They go on dates to the arcade, smoke doobies, and eat fried chicken on the terrace of the UES apartment where he lives (with his parents). But after his mom busts them and Carrie flees—with the pot in tow—the episode ends with her, Miranda, and Samantha smoking and laughing together. I love this episode because stoned Carrie is always funny, but mostly because it does capture that specific way that summer feels in New York City, especially when you’re young! It’s sticky, expansive, and it’s always, always a good time.—Laia Garcia-Furtado
“The Real Me”
Some of my favorite SATC episodes are the ones where Carrie is happily single (allegedly) and focusing on the other rich parts of her life. This episode, in which she has been tapped for a charity fashion show and is doubting her model cred at every single turn, more than fits the bill. There’s also a great mix of A/B plots that explore self-image: Charlotte has a “sad vagina,” Samantha is heavily invested in nude portraiture, Miranda wonders why a guy at her gym finds her pretty, and Stanford and Anthony provide a comedic glimpse into how toxic the queer dating landscape can be. The episode’s main plot, in my opinion, is the perfect portrait of Carrie as a flawed, multi-dimensional character—an independent, self-assured 30-something who can figure out how to build a successful, cosmopolitan life as a writer, but not how to tackle stage fright. Relatable! Kind of. When she finally hits the runway, Carrie eats it and becomes “fashion roadkill” as models walk around her. The cringe radiates off the screen. Yet her triumph comes not when she eventually gets up and completes her walk, but later, back at home. She catwalks around her iconic apartment in her underwear, as Cheryl Lynn’s confidence-boosting anthem “Got to Be Real” plays. Moments like this are what fuel my love for Carrie. She might fall—hard—but she always gets back up and recovers her fabulosity. How else would she have the life she has? The episode’s arc really showcases her resilience—something easy to miss when her anxious attachment style is activated through a Big or Aidan. I always feel all the feels when I watch this one.—André-Naquian Wheeler
“My Motherboard, My Self”
If you’re into gallows humor, this is your episode. After Miranda’s mother suddenly dies of a heart attack in Pennsylvania, Charlotte becomes the “Martha Stewart of death”; Samantha runs through 1,001 sex positions with the wrestling coach from NYU in search of her “lost” orgasm; and Carrie is spectacularly awful to Aidan, even after he purchases her a fabulously retro turquoise MacBook (with handle) when her old computer dies. It’s worth revisiting just for the moment when Samantha casually damns her fellow suburban mourners with the phrase, “Well, I’m not gonna find my orgasm in this town.”—H.M.
“Coulda Woulda Shoulda”
While certain Sex and the City subplots have aged badly, Miranda’s back and forth over whether to move forward with a pregnancy in “Coulda Woulda Shoulda” is handled with incredible sensitivity. Ditto Charlotte’s frustration over struggling to conceive, and Carrie’s qualms about telling Aidan that she had an abortion as a 22-year-old. Bringing some welcome comic relief: Samantha, who spends most of the episode in pursuit of a Birkin, only to find herself at odds with her client, Lucy Liu, after she uses the A-lister’s name to jump Hermès’s famously long waitlist.—H.M.
“Change of a Dress”
There are a lot of milestones in this episode—none of which are tackled conventionally. Charlotte attempts to tap-dance her way through a divorce. Miranda “fakes” a sonogram (“Everyone else is glowing about my pregnancy, when will I?”), and Carrie has an allergic reaction to the prospect of marriage—breaking out in a rash after trying on a puff-sleeved, rhinestone-covered wedding dress. Samantha, on the other hand, finds herself considering monogamy after falling for toxic bachelor archetype Richard.—H.M.
“A Vogue Idea”
Of course we love this episode, which features Miranda being cranky about her baby shower and Carrie getting hired to write a column for Vogue. Carrie initially fumbles her shot, making too many boy puns in her shoe column (and uttering the immortal line “I’m drunk at Vogue!”), but ultimately pulls it off. Women thriving in the workplace: We love to see it!—E.S.
“Anchors Away”
Of the many Sex and the City episodes that function as a paean to New York, “Anchors Away” is the most enjoyable to watch. (Notably, the team filmed it just after 9/11.) Having given birth in the previous season’s finale, Miranda adjusts to the realities of motherhood, in spite of telling the other girls to just think of Brady “as a big purse,” while the rest of the girls cruise sailors in honor of Fleet Week, with both Samantha and Charlotte taking the opportunity to turn flasher for the night. It also features the iconic scene in which Samantha posts angry flyers about Richard cheating all over Manhattan, with the support of a female member of the NYPD.—H.M.
“Plus One is the Loneliest Number”
No other Sex and the City episode quite matches up to this one when it comes to guest appearances. (Not even the L.A. ones can compare.) There’s Mario Cantone as Anthony Marentino, brought in to help organize the launch party for Carrie’s first essay collection; Amy Sedaris as her headset-wearing, ridiculously thirsty publisher (“All of Condé Nast is coming, including GQ—which has actual straight men”); and Candice Bergen returns as Carrie’s Vogue editor, the Miranda Priestly prototype Enid Frick.—H.M.
“Great Sexpectations”
Maybe it’s my JAP side showing itself, but I find Charlotte’s quest to convert to Judaism in order to marry her beshert, or soul mate, Harry, genuinely touching. It’s so much fun watching her get not once, but twice curved by a rabbi—but it’s even more fun to watch him finally accept her into the Jewish faith. As Charlotte once said, “There’s more to being a Jew than jewelry!”—E.S.
“The Post-It Always Sticks Twice”
Dating Jack Berger enabled Carrie to work a truly insane number of puns into her column—“The only thing as delicious as those first few bites of a truly great burger are those first few dates with someone truly great, like Berger… ”—so it’s almost a relief when he dumps her in “The Post-It Always Sticks Twice.” The girls’ lengthy discussion of this romantic faux pas—“I remember when breaking up over the phone was considered bad form”—makes you wonder how Carrie would ever cope with being ghosted, and Smith’s visit to TLR is peak Y2K nostalgia.—H.M.
“The Ick Factor”
“The Ick Factor” is without a doubt one of Sex and the City’s most touching episodes—revolving around Miranda’s gloriously no-nonsense wedding to Steve. (Miranda, while shopping for a wedding dress: “I said no white, no ivory, nothing that says virgin. I have a child. The jig is up.”) Then there’s Samantha’s breast cancer diagnosis, which elicits a tearjerking response from all of the girls—and a nice subplot in which Carrie’s American pragmatism jars with Alexander Petrovsky’s Russian take on romance.—H.M.
“Splat!”
When is the party really and truly over? “Splat!” tackles sexism and ageism head-on. Most dramatically, there’s Kristen Johnston’s appearance as Lexi Featherston, a “washed-up” ’80s socialite who falls to her death while having a cigarette at Enid’s Euro-intellectual-themed cocktail party. (Her parting words? “I’m so bored I could die.”) Then there’s Enid herself, who delivers a heartbreaking speech to Carrie after meeting Petrovsky. “It’s not fair. He’s my age, and you’ve got him. And I am in no-man’s-land, literally. No man anywhere. Men can date anyone, any age, but let’s be frank… most of them prefer the bimbos. So if you’re a successful 50-something woman... there’s a very small pool.”—H.M.
Listen to Sarah Jessica Parker talk Sex and The City and more on this episode of The Run-Through here.