‘Sex and the City’: The 20 Best Episodes, Ranked

(Season 6, Episode 14)

Despite being known for its sardonic humor and farcical plot points, the show’s most earnest storylines — which never veer into the overly sentimental — invite some of its best moments. In “The Ick Factor,” Miranda finally gets over her commitment issues and proposes to Steve (David Eigenberg), but she stays true to herself by keeping the wedding as low-key as possible. As she says while wedding dress shopping: “I said, “no white, no ivory, no nothing that says ‘virgin.'” I have a child. The jig is up.” 

But the real tear-jerker of the episode arrives moments before the ceremony when Samantha discloses her breast cancer diagnosis to Carrie. The pair initially decide to keep the secret between themselves as to not ruin Miranda’s big day but Charlotte and Miranda ultimately find out about the condition, leading to a sobering moment between the four friends. But even a breast cancer diagnosis can’t get in the way of the show’s witty one-liners. After Samantha’s boyfriend Smith (Jason Lewis) shaves his own head to support her throughout chemotherapy treatment, Carrie’s voiceover says it all: “That night, Smith gave Samantha the best head of her life.”

(Season 1, Episode 4)

Many of the best “Sex and the City” episodes are when Carrie is taken out of the comfort of her Upper East Side apartment, and the suave coterie she normally hangs around, and is forced to mingle with the “normies.” In this case, that entails a fling with a 20-something boy named Sam (played by Timothy Olyphant) who has a tongue piercing and like all 20-something year-olds, knows all the city’s “B people”: busboys, bouncers and bartenders.  

Meanwhile, Charlotte’s new man asks to have anal sex, which leads to a lively debate between all four ladies in the back of a cab. Samantha says it’s “fabulous,” but Charlotte, of course, politely declines.  

(Season 2, Episode 1)

One of Carrie’s most memorable fashion moments occurs in the dugout. After breaking up with Chris Noth’s Mr. Big (the first big break of many throughout the series), she and the girls attend a Yankees game with the hopes of rebounding with a baseball star. In true Carrie fashion, she shows up to the stadium in a fur coat, black dress and heels –  lit cigarette in hand. The show’s outlandish outfits are always compelling, but they’re given extra dynamism when worn at the ballpark rather than Fifth Avenue. 

(Season 3, Episode 1)

Any episode that sees Miranda let loose is a winner in our book. To kick off Season 3, the posse ferrys to Staten Island for the New York Fire Department’s male calendar finalists benefit, where Carrie is charmed by a politician (John Slattery) , Miranda gets drunk (as she excitedly exclaims after one Long island Iced Tea)  and Charlotte finds out what toxic masculinity is after meeting a man with anger management issues. Meanwhile, Samantha lives out her sexual fire station fantasies but before she has time to put her clothes back on, a real fire breaks out and she’s left in the station alone — naked and humiliated.  

(Season 3, Episode 4)

Oftentimes, the episodes that don’t age well are also some of the most entertaining to re-watch. One such episode is “Boy Girl, Boy Girl” when Carrie finds out the guy she’s dating is bisexual, which leaves her and the rest of the ladies absolutely confounded. As Carrie has a crisis over brunch, Samantha delivers one of her best lines: “I’m a try-sexual, I’ll try everything once.” 

(Season 3, Episode 12)

This episode sees each friend caught up in a fib — Carrie is hiding her affair with Big from Aidan, Miranda says she’s a stewardess to find a date to Charlotte’s wedding to Trey (Kyle MacLachlan), Samantha fakes understanding the accent of Trey’s Scottish cousin to get him into bed, and Charlotte lies to herself that she’s OK with marrying Trey despite the fact that he can’t “get it up.” It all begs the everlasting question: Is honesty the best policy? The answer: Not necessarily. As Aidan (John Corbett) says to Carrie in a particularly heart-shattering breakup scene after she reveals her infidelity, “I just wish I didn’t know about this.” But all’s well that ends well, as the girls are reminded of the only people who will be there for them no matter what: each other.

(Season 6, Episode 18)

In one of the most memorable episodes of the series, socialite Lexi Featherston (Kristen Johnston) makes her grand exit by falling out of a balcony window after declaring that “New York is over” and “I’m so bored I could die.” And it turns out New York may actually be over — well, at least for Carrie, as Aleksandr (Mikhail Baryshnikov) has asked her to move with him to Paris. Carrie is immediately bombarded by a million questions from Charlotte, Samantha and Miranda, but pushes away lingering doubts and quits her job to follow her fairytale. It feels like the end of an era, and tugs at the heartstrings when Miranda pleads with Carrie to reconsider, saying that she’s making a mistake.

(Season 4, Episode 11)

After the revelation that Miranda is pregnant with Steve’s baby and doesn’t plan on keeping it, “Sex and the City” gets refreshingly real about abortion. Samantha reveals she’s had two, and Carrie had one after a drunken night at The Tunnel with a random waiter. But after Carrie spills the beans to Aidan — and can’t tell him the truth about her own past — she wonders if she made the right decision in not informing the father, just as Miranda is grappling with the same dilemma. Curious, Carrie returns to the restaurant where the waiter worked and finds him still there, unable to recall who she is, renewing her confidence in her choice. Ultimately, Miranda decides to go through with the pregnancy, and Carrie comes clean to Aidan about her abortion. In Aidan’s annoyingly perfect fashion, he shows no judgment and Carrie is able to let go of her shame surrounding the situation.

(Season 6, Episode 7)

After Carrie wakes up to a break-up note from Berger (Ron Livingston) written on a post-it — “I’m sorry. I can’t. Don’t hate me” — she becomes enraged. At lunch with the girls, a newly engaged Charlotte (to Harry, played by Evan Handler) assures Carrie that everything happens for a reason. But Carrie is annoyed by the fact that men seem to get off scot-free when it comes to breakups, and women always have to learn something from them. Determined not to learn anything, when Carrie runs into Berger’s friends at Bed (the city’s hottest new club), she yells at them on behalf of all men, breaking her vow to keep it cool. To cheer herself up, Carrie wants only one thing: to get high. Unfortunately, after she and Samantha get the goods, they’re stopped by the police, forcing Carrie to explain to them her terrible day and present the evidence. The cop lowers her punishment to a ticket for smoking in a bar — when asked why he couldn’t just let her off, he replies: “I’m sorry. I can’t. Don’t hate me.”

(Season 6, Episodes 19-20)

Yes, this is technically two episodes, but they will forever be grouped together as the show’s finale. As Carrie prepares to say goodbye to New York City and bonjour to Paris, who comes knocking on her door but Mr. Big. As he confesses that he made a mistake in her playing with her heart all those years, Carrie finally lets him have it, yelling down the street: “I don’t live here anymore!” But after she arrives in Paris and begins her new life with Aleksandr, Carrie finds it’s not really the city of dreams. Instead, she’s at Aleksandr’s beck and call and loses her prized “Carrie” necklace — perhaps a sign that she’s losing herself. When Charlotte comes to check on Carrie’s apartment and hears a voicemail from Big confessing his love for her, the girls rally around him and give him the mission to “go get our girl.”

“Part Deux” shows that the rest of the crew is going through changes of their own — Samantha is getting her bearings back after battling breast cancer, Charlotte and Harry are struggling to adopt and Miranda becomes a caretaker for Steve’s mother. Back in Paris, the final straw is when Carrie ditches a party thrown by some local fans for Aleksander’s art exhibit, where he leaves her alone on a bench. Sitting alone, she finds her “Carrie” necklace and takes off into the night, walking right past the car carrying Big — one of several gasp-worthy moments in the final episode. Another is when Aleksandr slaps Carrie, and then bumps into Big in her hotel lobby. No matter your personal feelings about Big, nothing feels more fated than Big telling Carrie “you’re the one” as the Eiffel Tower twinkles in the background.

And it’s not just a happy ending for Carrie — Charlotte and Harry get their baby, Samantha gets her sex drive back (and Smith Jerrod tells her he loves her) and Miranda revels in the love of her family. As Carrie struts down the New York streets once again, it’s revealed that Mr. Big is now just “John” in her phone — finally putting the two on equal footing for the first time since the show’s premiere.

(Season 6, Episode 12)

After a somewhat bruising time for Carrie — ditched via Post-It note, feeling the chill of loneliness as friends pair off — comes the strange delight of possibility. The show completely sells the idea that Carrie would fall for Aleksandr; it also injects its endgame with a soaring sense that anything might happen, which powers it through Carrie moving across the Atlantic and, finally, back again.

(Season 3, Episode 15)

This episode features one of Carrie’s most memorable one-off relationships — and puts a perfect button on it, with Carrie leaving her young paramour to be chewed out by his mom, with whom he lives. It also epitomizes the show’s sense of endless summer, with the characters perpetually bathed in golden light and living at leisure. But the strongest aspect of the episode is Samantha’s engagement with a new client (Kat Dennings), who retains Samantha as a publicist and whose precocious fluency in the raunch language of adults prompts reflections on what it means to be a kid — a touching step into character study for a show whose four central characters purposefully don’t have backstories.

(Season 3, Episode 9)

Samantha’s storylines can bend this show’s elastic comic universe a bit too far at times, and yet this episode, in which her extensive, explicit complaints about her partner send Charlotte running, provides the character a relatively grounded and yet richly Samantha showcase. It’s a worthy counterbalance to other, more wistful, storylines here, like Miranda dealing with the aftermath of her breakup with Steve and Carrie being pursued by an ardent, cheating Big.

(Season 4, Episode 1)

If you toss the too-goofy-by-half Samantha storyline involving seducing a monk, this episode is a pretty perfect way to open the season — with Miranda and Charlotte coping with loneliness and Carrie felled by it, when no one comes to her birthday party. (The sequence of her dropping the cake in the street merges physical comedy and heartbreak beautifully.) If it sounds like a morose beginning, it’s not: Instead, it provides a way for all the characters to actually contemplate the future. Not such a bad place to start things.

(Season 2, Episode 4)

One of the few episodes from the show’s earliest going to hit the heights it eventually would, and a good representative of what the first couple of seasons could do well. Miranda, Charlotte’s, and even Samantha’s plotlines are pleasantly grounded, while Carrie’s — the botched New York cover shoot and subsequent humiliation — is among the series’ most memorable. It’s also an appropriately over-the-top way to tie together the episode’s theme of each of the women feeling in her own way like a fraud.

(Season 5, Episode 6)

A deeply apt merging of Carrie’s professional and personal lives — in which Carrie feels seen in all the wrong ways by book critic Michiko Kakutani and, perhaps more harshly, judged unjustly by a fellow ex of Aidan (Nadia Dajani, in a memorable cameo as “Nina Katz”). Trying to overcome preconceptions is a rich vein to plumb for a show widely seen as having been about fashion and sex solely. To wit: Elsewhere, we see the sort of rich and deep friendship the show was able to pull off in its later seasons, with Samantha sacrificing for the happiness of Miranda, a new mom who’s sinking under the weight of responsibility.

(Season 3, Episode 11)

For all that she’s the protagonist, Carrie is no heroine, and that’s borne out in this episode where she’s forced to face down the consequences of her actions, with an angry Natasha making clear exactly what Carrie’s cost her. Charlotte’s weighing in on the matter gives Kristin Davis a nice note to play, while Samantha’s fielding a request from a partner to get an AIDS test contributes to the episode’s sense of giving way to a new level of frankness. Finally and to some viewers most memorably, Miranda falls in love with a sandwich.

(Season 4, Episode 8)

By far the deepest dive into any character’s family life comes when Miranda’s mother dies; that Carrie sees in it a parallel to her laptop dying is not a bug of a character written to be narcissistic but a view into just how deeply she’s struggling with Aidan. Her declaration to him that her “whole life was on that computer” makes clear, with the show’s brutal effectiveness, that he is not destined to be a part of it in the long term.

(Season 6, Episode 9)

Carrie’s independence — not a consistent trait throughout the series, and ultimately sold out at least a bit by the finale — is in full flower in this episode, in which she faces down a society matron (Tatum O’Neal) who refuses to believe Carrie’s life has as much meaning as the life of a mother. While great meaning was pulled from Miranda and Charlotte’s becoming parents, Carrie was never meant to be one — and the show acknowledges this in a plainspoken and ultimately celebratory way.

(Season 4, Episode 18)

This episode provides a winsome shift forward for each of the characters — Samantha away from Richard, a part of the show for a punishingly long time; Charlotte back into dating; Miranda into motherhood; and Carrie into the unknown, as she says farewell to Big once again. The show has previously done heartbreak and rage but never melancholy at this indulgently massive a scale. It functioned both as a turning point in the show growing grander in its emotional palette and (though it was filmed before the events of Sept. 11, 2001) as a tribute to its mourning, resilient city, with a closing monologue (“seasons change; so do cities”) that is at once proudly corny and stirring all the same.