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 countless flings with guest stars ranging from Bradley Cooper to Vince Vaughn. Then there are those that battle 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 “just settle down”; and the omnipresent dilemma of whether or not to have children when everyone seems to “expect” you to. There were 93 instalments in the drama’s original six-season run – some good, some bad, and some deeply ugly. Ahead of the Sex And The City reboot, here are the best ones to rewatch now.
1. “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.
2. “The Baby Shower”
Nothing good happens when the Big 4 leave their natural habitat of Manhattan – aggressive bikini waxes in LA, 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-coloured condoms.
3. “Take Me Out To The Ballgame”
Each main character is peak “herself” in this episode. Carrie agonises over her relationship with Mr Big – both in Manhattan (“a deserted battlefield, loaded with emotional landmines”), and at a Yankee game in the Bronx, 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 victimised 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.
4. “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 opthalmologist. (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.
5. “The Attack Of The 5’10” Woman”
This episode largely centres 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 sachets 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.” Also, Charlotte is there.
6. “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.”
7. “My Motherboard, My Self”
If you’re into gallows humour, 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.”
8. “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.
9. “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 honour 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.
10. “Plus One Is The Loneliest Number”
No other Sex And The City episode quite matches up to this one when it comes to cameos. (Not even the LA episodes compare.) There’s Mario Cantone as Anthony Marentino, brought in to help organise 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. For what it’s worth, this is also the beginning of Carrie’s Berger chapter. Oh dear God, the puns.
11. “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 heartwarming response from all of the girls – and a nice Henry James-esque subplot in which Carrie’s American pragmatism jars with Alexander Petrovsky’s Russian take on romance.
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 heart-breaking 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.”
From British Vogue