Sex And The City at 25: How the pilot holds up today

It’s hard to imagine a time when Carrie, Miranda, Charlotte, and Samantha weren’t part of the pop-culture universe. For 25 years we’ve been drinking cosmos and meeting for brunch in honor of Sex And The City’s fabulous friends. Regardless of how things eventually turned out for them—another season of And Just Like That… arrives later this month—the fact is these characters helped shape the perception of women for an entire generation by openly talking about sex and sharing the intimate details of their love lives in ways no one had ever done on TV (except for maybe Dr. Ruth).

For six seasons we cheered their victories, judged their decisions, marveled at the hell that was the Manhattan dating scene in the late ’90s and early ’00s, and wondered why anyone would willingly put themselves through all that. And we cried when we had to say goodbye in 2004, but then there were two movies, a prequel series, and a 2021 reboot, so maybe these women will never truly leave us (even Samantha is sort of coming back).

A lot has changed since the pilot first aired on June 6, 1998—exactly 25 years ago today. Nothing demonstrates that more than going back to watch that first half-hour episode now. It’s not just that it’s dated—and, hoo boy, is it ever—but it’s jarring to watch what feels like a half-formed idea of a show that never really came to be. There are recognizable elements to be sure, but creator Darren Star had yet to nail the format this early into the run. That’s understandable. He didn’t really have a template to work off of—because Sex And The City would eventually become its own template.

In the beginning, there was sex

By the time Sex And The City premiered, HBO had been dabbling in original programming for several years. It wasn’t until the late 1990s that the network really started ramping up, though. Movies were still HBO’s bread and butter (the initials stood for “Home Box Office,” after all), but with DVDs starting to cut into its subscriber base, executives pivoted to episodic television. After finding some success with The Larry Sanders Show in 1992 and, to a lesser extent, shows like Arli$$ in 1996, executives realized they had a huge advantage over broadcast networks. With the acclaimed prison drama Oz HBO started pushing into edgier series that couldn’t be done anywhere but premium cable—shows full of swearing, violence, and, yes, sex. Lots and lots of sex.

It was Darren Star who brought Sex And The City to HBO. He’d previously had hits on Fox with Beverly Hills, 90210 and Melrose Place, but he wanted to do something more mature outside the confines of primetime TV. He teamed up with journalist and author Candace Bushnell to create the show based on her experience as a sex columnist for the New York Observer and her book anthology based on those columns. Together, they sold the show to an eager HBO.

The key to Sex And The City was that it wasn’t just about sex. Despite the provocative title, the show wasn’t meant to titillate like the erotic programming after hours on HBO’s sister network Cinemax that earned it the nickname “Skinemax.” Instead, it starts as a frank conversation about sex between Carrie (Sarah Jessica Parker)—a stand-in for Bushnell—and the audience, in the same way a newspaper columnist converses with their readers. That would later expand to incorporate Carrie’s circle of friends, who provide the material for her columns and the ongoing storylines in the series. Darren Star and his writing staff eventually realized that once the audience became acclimated to the brutal honesty of its explicit sex scenes, they had to give us characters we’d still want to follow when they left the bedroom or the show wouldn’t work. But it took a bit of tinkering to get there.

Revisiting the pilot: A meet not-so-cute

What jumps out immediately watching the pilot now is how different Carrie is from the character we would come to know. Working in an unfamiliar apartment (the set had not been built yet), typing away on a chunky desktop, her hair swooped up on top of her head, she looks right at the camera and breaks the fourth wall: “How the hell did we get into this mess?” Her hair is shorter, her makeup heavier, her clothes darker. In one scene she wears a gray trench coat over a black dress with no jewelry. She’s Carrie Bradshaw, but she’s not Carrie Bradshaw. Not yet, anyway.

This version of Carrie talks straight to the camera a few times in the pilot. It’s a little off-putting, frankly. Carrie’s signature voiceover narration is also part of the episode. That element would stick around for the entirety of the show’s run, though the visual equivalent fortunately does not. There are also random interviews sprinkled throughout with New Yorkers talking about their dating lives and philosophies in documentary-style interviews. The men are labeled on-screen as “Toxic Bachelor” and the women as “Unmarried Woman.” If that’s supposed to be a joke, it’s a trite one. Miranda (Cynthia Nixon) and Charlotte (Kristin Davis) are identified as the latter. Samantha (Kim Cattrall) gets a pass, but she does voice what becomes the big (and somewhat antiquated) question of the episode: Can women have sex like men?

It’s a reminder that even as it later experimented with the tropes of male and female identities and gender roles, early on the show often reverted back to conventions and worn-out ideas of sexuality. Or maybe they just seem worn out 25 years later. There’s a scene where Samantha goes home with a guy who doesn’t want her to stay the night, and although she says she’s fine with that, the look on her face says that all her earlier talk about sex without feelings was false bravado. Knowing what we know about Samantha now, it feels like the character wasn’t completely there yet. As for characters like Miranda, Charlotte, and Stanford (Willie Garson), they’re more recognizable, if significantly toned down.

The good with the bad

There are many moments in the pilot when it seems like you’re watching a bargain knockoff of Sex And The City rather than the genuine article. But there are also a few times when you can see the sparks of something familiar. It’s fun going back to the beginning and seeing how Carrie and Mr. Big first meet. He literally bumps into her on the street as she’s leaving the apartment of another man she’s just slept with. She walks away all flustered as he gives her one of his little teasing waves. Unlike Carrie, Big arrives on the scene fully formed as the character we know. He even has an iconic final line. When she asks him if he’s been in love before, he says, with his typical Big grin: “Abso-fucking-lutely.”

This push-and-pull between Carrie and Mr. Big typifies what fans came to love (and some grew to hate) about the show in later seasons. From that first chance meeting their chemistry is undeniable, but there’s something about him that seems aloof and unobtainable. Separating true love from sexual attraction and finding that balance in a relationship is an ongoing struggle for all the characters in Sex And The City, and as flawed and weird as the pilot episode is, it still manages to successfully convey that theme.

It also gives us one of the most poorly aged lines in the show’s entire run. When Samantha points out Mr. Big to Carrie across a crowded club (another chance meeting that would become a hallmark of the show) she describes him as, “The next Donald Trump, except he’s younger and much better looking.” Guess that was a compliment in New York City in 1998. Whatever you think about the Sex And The City pilot, at least we can say there are some cultural phenomena that have fared worse in the last 25 years.