In 1998, Sex and the City debuted on HBO and changed not only the television landscape but also the way we think and talk about sex, relationships, and fashion. Created by Darren Star and based on Candace Bushnell’s wildly popular column and book, the show redefined women’s relationships to men, friends, cupcakes, shoes, and singlehood itself.
And while their stories keep coming in the spin-off And Just Like That…, the original remains the gold standard of glamorous single-woman TV: Carrie (Sarah Jessica Parker), Charlotte (Kristin Davis), Miranda (Cynthia Nixon), and Samantha (Kim Cattrall) are still the friends we love to laugh and cry with, roll our eyes and cringe at, and go clubbing and shopping with. So with all six seasons of Sex and the City streaming on Netflix, raise a Cosmo toast to the beauty of Manolos and the bonds between girlfriends and cue up these 18 essential episodes.
Season 1, Episode 4: “Valley of the Twenty-Something Guys”
After a bit of an awkward, trying-too-hard start — albeit with flashes of fun and brilliance — Sex and the City really hits its stride in its fourth episode, which nails both the shameless fun and total indignity of being a thirtysomething woman having a sex life in New York City. Samantha reports great sex with a guy in his 20s, and Carrie has a fine time with his friend (played by a young, smoldering Timothy Olyphant) but is rudely awakened, literally, in his disaster of a toilet-paper–free apartment. Incidentally, it’s an authentic NYC location; director Alison Maclean scouted some “mind-bogglingly gross” apartments for the shoot, as she recalled in Sex and the City and Us. Meanwhile, Charlotte’s new beau requests a controversial sex act, prompting the women to convene an emergency meeting in the back of a cab to debate the pros and cons. An absolutely iconic conversation ensues. (Miranda: “If he goes up there, there’s going to be a shift in power.”) It was SATC’s first watercooler moment that was absolutely NSFW, and it wouldn’t be the last.
Season 1, Episode 9: “The Turtle and the Hare”
Introducing the women of America to shameless vibrator addiction! Everything here sets the perfect tone to demystify and destigmatize the act of pleasing oneself. The vibrator in question is “The Rabbit,” and, well, it’s cute! It’s like a bunny. “It’s pink! For girls!” Charlotte proclaims happily upon seeing it for the first time at the Pleasure Chest sex toy shop in the West Village. We could unpack that statement alone at Ph.D dissertation length, but we’ll cut to the chase: Charlotte, the demure one, is the gal who gets addicted, which paves the way to acceptability. As a result of Charlotte’s love, and a burgeoning online market that allowed women to order vibrators without a shred of self-consciousness, The Rabbit became the best-selling sex toy of all time.
Season 1, Episode 10: “The Baby Shower”
Here’s Sex and the City in its sweet spot, celebrating the single life as not just OK, but as an actual triumph over smug, married, baby-obsessed coupledom. “The Baby Shower” has the women venturing to the suburbs to celebrate their former party girl friend Laney’s (Dana Wheeler-Nicholson) pregnancy. They arrive dressed in mostly black, looking like out-of-place rock stars in bright and shiny Connecticut. They give Laney cigarettes, scotch, and condoms as presents. (Except Charlotte, of course, who remembered to get a proper baby gift.) If you’ve been a single woman long enough, you probably feel very seen by this depiction.
Season 2, Episode 4: “They Shoot Single People, Don’t They?”
Sex and the City goes meta! Carrie shows up hungover, late, and uncaffeinated to a New York magazine shoot, and the resulting predictably unflattering photo of her makes the cover, with the headline “Single & Fabulous?” It’s a riff on the shocked and judgy coverage the show had gotten in its first season, and it was also a bit prescient. The four main cast members landed on Time’s cover a year later, albeit looking more fabulous, and the headline was a bit more upbeat, but it still snuck in some nagging doubt about this whole single gal thing: “More women are saying no to marriage and embracing the single life. Are they happy?” The situation mirrors the series’ opening credits, which spotlight Carrie’s glamorous life — she’s famous enough to have her own bus ad! — only to immediately knock her down, splashing dirty city water all over her fashionable outfit.
Season 2, Episode 18: “Ex and the City”
In the Season 2 finale, Carrie and her frustratingly on-and-off boyfriend Big (Chris Noth) reconnect to “try and be friends or something,” as she says, when he drops the bomb that he’s engaged to 26-year-old Natasha (Bridget Moynahan), who he’s been dating for just five months. When Carrie naturally freaks out, Big tells her that he chose Natasha because she’s simple instead of complicated like Carrie. Then Big and Natasha, in their infinite wisdom, invite Carrie to their engagement party. This leads up to the indelible scene in front of The Plaza in which Carrie pays tribute to Barbra Streisand in The Way We Were, dramatically telling Big, “Your girl is lovely, Hubble.” The frustration/cringe/swoon of this episode sets the blueprint for every Big and Carrie cycle to come.
Season 3, Episode 11: “Running with Scissors”
The one where Carrie says to Big, “We’re so over, we need a new word for ‘over,’” and yet… those of us watching know otherwise. Carrie’s affair with the now-married Big reaches dire depths as an alarmed Charlotte and Miranda get clued in to the goings-on, putting a strain on their friendship. Charlotte asks Carrie if she ever thinks about how Big’s wife, Natasha, would feel if she found out, and even calls Carrie’s bluff when Carrie claims that she does: “No, you don’t! You think about what will happen to you if she found out. You don’t think about her, she’s just the idiot wife. You don’t know anything about her.” It’s a raw moment in this anti–rom-com deconstruction of Big and Carrie’s tumultuous dynamics.
Season 3, Episode 12: “Don’t Ask, Don’t Tell”
Charlotte is marrying WASPy dream guy Trey (Kyle MacLachlan) without having sex with him beforehand, a distressing decision. Carrie manages to pull major focus by confessing to devoted beau Aidan (John Corbett) that she cheated on him with… you guessed it, Big! All four women are at their most here: Carrie is rendered infuriatingly indecisive by her toxic infatuation with Big. Charlotte foolishly moons over the romance of no sex before marriage (and snaps, hilariously, at Samantha, “Can you please not use the F-word in Vera Wang?”). Miranda tests a guy by telling him she’s a flight attendant instead of a lawyer, proving her point that men don’t want powerful women. And Samantha sleeps with a guy in the wedding party with an inscrutable accent and a kilt. Wedding day perfection all around.
Season 3, Episode 15: “Hot Child In the City”
Youth is often idealized in the fashionable circles the women run in, but this episode highlights the unexpected benefits of aging. Samantha gains a new appreciation for her own ordinary childhood after she’s hired to plan a wealthy 13-year-old’s bat mitzvah and sees firsthand how early certain young girls start to behave like adults. Carrie meets a comic book store owner but has to decide if she can be with a man who lives with his parents and appears in no rush to grow up. Meanwhile, Miranda re-experiences the awkwardness of adolescence when she gets braces.
Season 4, Episode 8: “My Motherboard, Myself”
A superlative episode in a strong season, “My Motherboard” starts with all the elements of any classic SATC episode — Carrie’s commitment issues with Aidan pop up yet again when she refuses his help with a broken laptop, and Samantha is dating a wrestler which leads to some great sexual comedy. But it takes a turn toward the very real when Miranda’s mother dies. The scene in which an overly attentive bra saleswoman triggers Miranda’s grief showcases Nixon’s extraordinary talent. And the ending when the women walk behind the casket with Miranda shoots to the heart of what Sex and the City is all about — female friends as found family.
Season 4, Episode 11: “Coulda, Woulda, Shoulda”
The show continues to take a deeper turn as Miranda gets pregnant and tells her friends she plans to get an abortion. Charlotte, who has been struggling to get pregnant, walks out. Carrie goes to see a waiter named Chad, who doesn’t know that she had an abortion after their one-night stand years ago. SATC has plenty of sexy fun, but this episode reminds us of the gravity of sex and how its meaning can change throughout our lives. It also makes a bold statement — for its time and even more so for ours — about the importance of women’s control over their own bodies. Meanwhile, Samantha lusts after a Birkin bag, which is just the silly release valve we need here.
Season 4, Episode 15: “Change of a Dress”
A divisive episode, especially for the Carrie haters. But for those of us who have found ourselves very much not wanting to marry someone we’ve been engaged to, it’s relatable and real — if also cringeworthy. Carrie’s wearing her engagement ring on a chain around her neck instead of on her finger and forgetting to mention her fiancé, Aidan, when she runs into an acquaintance who asks what’s new. Aidan is suggesting destination wedding ideas, and Carrie is demurring. The memorable climax comes when Carrie and Miranda try on terrible bridal gowns as a joke, and Carrie has a panic attack, breaking out into hives. We’re left to wonder whether she’s still going to go through with this, and the storyline makes a very SATC statement about the pressure to marry the right kind of guy — even if it’s obvious he isn’t right for you.
Season 4, Episode 18: “I Heart NY”
This bittersweet episode might be the one time we can truly believe in the idea of Big and Carrie together — and, tellingly, it’s because he’s leaving town and moving to Napa. Their one last perfect night together in his all-but-packed apartment includes them doing the twist as “Moon River” plays on a turntable. Moved to do something quintessentially New York, they go on an impromptu carriage ride in Central Park, but they’re interrupted by a call: Miranda is in labor, and the romantic dream is broken. Eerily enough, this episode was written and shot before the September 11 attacks, but it aired the following January, playing like a tribute to a broken city. Parker’s closing narration was written before the mass tragedy, but recorded just weeks afterwards: “Seasons change. So do cities. People come into your life and people go. But it’s comforting to know the ones you love are always in your heart. And, if you’re very lucky, a plane ride away.” The writers had debated, pre-9/11, whether the title of the episode was too cheesy, but it seemed perfect in a post-9/11 world.
Season 5, Episode 1: “Anchors Away”
The first episode written after 9/11 leans into SATC’s fizzy approach to lifting spirits and cheer for New York City. A very single Carrie declares the city to be her great love and vows to enjoy it to its fullest extent. Writer Liz Tuccillo pitched the idea of the episode culminating at a Fleet Week party, recalling her own love of that annual event when crowds of young military officers flood city streets in uniform. Flirting and fun ensue, offering a comforting sign that everything is still OK, and there’s a light, sweet ending: When the officer Carrie flirts with complains about some aspects of New York City, she’s immediately turned off. “I can’t have nobody talkin’ shit about my boyfriend,” she says.
Season 6, Episode 2: “Great Sexpectations”
By this late date in its run, Sex and the City confidently strides through its paces, easily toggling among the sexy, the serious, and the silly without breaking a sweat. Carrie’s loving the banter and romance with new guy Jack Berger (Ron Livingston), but not feeling it in bed. Samantha drags the others to a trendy, ultra-healthy restaurant called Raw just to ogle a particular waiter — the introduction of her unlikely real-deal love, the smoldering and sweet Smith (Jason Lewis). Miranda falls in love with her TiVo. And Charlotte brings the gravitas with her touching, surprising decision to convert to Judaism so she can marry her divorce lawyer, Harry (Evan Handler), an endgame we never could have predicted for WASP queen Charlotte.
Season 6, Episode 7: “The Post-It Always Sticks Twice”
Berger delivers the show’s most infamous breakup, leaving Carrie a Post-It note: “I’m sorry. I can’t. Don’t hate me.” This succinct message encompasses multitudes about dating in New York City — the simultaneous cowardice of the delivery and, still, his need to be liked. Berger, for his part, is one of the series’ best-drawn male characters: charming yet preening, pathetic yet romantic, desperate yet a better match for Carrie than Big ever seemed. Their short courtship is a thrill precisely because you can’t tell if she’s finally found her person or is about to be flattened. Here she gets her terse answer.
Season 6, Episode 9: “A Women’s Right to Shoes”
While sex is the primary focus of the series, some of the best SATC episodes focus on the women proudly asserting their singlehood. In this episode, Carrie attends a baby shower for her friend Kyra (Tatum O’Neal) and discovers at the end of the night that her new Manolos are missing. Not only does Kyra downplay the significance of Carrie’s loss and berate her for paying so much for what she considers a needless luxury, she implies that her status as a mother is loftier and more mature than Carrie’s childless, shoe-collecting state of existence. Carrie’s frustration builds as she considers the injustice of the praise and gifts women receive for marrying or having children, when single women get no such opportunities to be celebrated outside these milestones. In the end, Carrie devises the perfect way to get her shoes and make a statement about this hypocritical cultural norm.
Season 6, Episode 14: “The Ick Factor”
Some very SATC plot points are popping off — Miranda and Steve are having a small community garden wedding, and Carrie is feeling weird about new suitor Aleksandr Petrovsky (Mikhail Baryshnikov) writing her songs and reading her poetry. But things take a surprising turn into very serious territory when Samantha, investigating the possibility of getting breast implants, finds out that she has breast cancer. Suspicious that something is going on, Miranda forces Samantha to share her news even though it’s Miranda’s wedding day — one of the best moments of friendship in the series.
Season 6, Episodes 19 and 20: “An American Girl in Paris, Part Une” and “Part Deux”
Even if you hate the fact that Big and Carrie end up together, there’s a lot to love in the two-part finale of the series. Carrie moves to Paris to be with Petrovsky, despite a boatload of ambivalence. But the decision isn’t all bad, since we get plenty of swooning shots of Paris and the dress to end all dresses, plus one grand gesture before she’s back where she belongs. The other women’s storylines wrap up less cinematically, but more reasonably, and with shots of genuine pathos. Miranda telling Big “Go get our girl” is everything we love about Sex and the City in four perfectly delivered words.
Additional reporting by Ananda Dillon.
