It’s June 6, 1998. Bill Clinton is in the White House. People are still mourning Princess Diana. And on a Sunday night, HBO—a network then mostly known for boxing and The Larry Sanders Show—dropped a half-hour pilot that would change how women talked about their lives forever. But if you go back and watch the first episode Sex and the City today, it’s jarring. It’s weird. It’s almost a different show.
Most fans remember the puns, the puns, and the Cosmopolitans. They remember the fashion. But the pilot, titled simply "Sex and the City," feels more like a gritty mockumentary than the glossy, aspirational fantasy it became by season three. Carrie Bradshaw, played by Sarah Jessica Parker, looks directly into the camera and talks to us. She breaks the fourth wall constantly. There are random "man on the street" interviews with anonymous New Yorkers complaining about their dating lives in grainy, black-and-white-ish footage. It’s cynical. It’s dark. Honestly, it’s kind of a bummer.
The Night Everything Changed for Carrie Bradshaw
The premise is basically an ultimatum. Carrie’s friend Elizabeth, an Englishwoman who is clearly a stand-in for the real-life author Candace Bushnell’s social circle, gets dumped by a guy who used her for her "pre-war elevator building." This triggers Carrie’s big thesis for the episode: can women have sex like men? By "like men," she means without feeling anything. Just pure, transactional, physical release.
It’s a question that feels dated now, but in 1998, it was revolutionary for television. We meet the core four, though they aren't quite "them" yet. Miranda is cynical but less polished. Charlotte is surprisingly experimental compared to her later "Park Avenue Princess" persona—she actually tries to have "sex like a man" in this episode, which feels totally out of character if you’ve only seen the later seasons. And Samantha? Samantha is already Samantha. Kim Cattrall walked onto that set and knew exactly who that woman was from frame one.
Then, there’s the meeting. The big one.
Carrie is walking down the street, drops her purse, and a tall, dark, handsome man in a limousine stops to help her. It’s Mr. Big. Chris Noth wasn’t supposed to be the series-long lead; he was just a guy in the pilot. But the chemistry was so immediate that the producers knew they’d found their "toxic king." He calls her "Kid." He smirks. He drives away. It’s the start of a decade-long saga of emotional unavailability that launched a thousand therapy sessions for viewers.
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Why the Pilot Feels Like a Different Universe
If you haven't seen the first episode Sex and the City in a while, the production value will shock you. It’s shot on film, but it’s moody. The lighting isn't bright and "sitcom-y." New York City looks lived-in, a bit dirty, and frantic.
One of the strangest things is the "Skipper" factor. Remember Skipper Johnston? He’s Carrie’s friend, a "nice guy" web developer who is desperately in love with Miranda. He’s a huge part of the first season, but he eventually just... disappeared from the show entirely. In the pilot, he represents the bridge between the old world of dating and the new, digital age. He’s vulnerable in a way the show eventually stopped allowing its male characters to be unless they were primary love interests like Aidan or Harry.
Also, let's talk about the interviews. The pilot features a guy named "Capote Duncan," a boutique owner who bragged about his conquests. These segments were pulled directly from the vibe of Candace Bushnell’s original New York Observer columns. They gave the show a journalistic edge. Creator Darren Star eventually realized that the chemistry between the four women was way more interesting than what random New Yorkers had to say, so the fourth-wall breaking and the interviews were phased out by the end of the first season. Thank goodness for that. The "talking head" style made it feel like a documentary on the Discovery Channel about the mating habits of Manhattanites.
Realism vs. Fantasy: The Fashion Evolution
Everyone talks about the tutu. That iconic tulle skirt Carrie wears in the opening credits (which cost $5 in a bargain bin, according to costume designer Patricia Field). But in the actual first episode, the fashion is surprisingly muted. Carrie wears a lot of black. She wears a slip dress that looks like something you’d actually find in a thrift store, not a $4,000 vintage Dior piece.
The show hadn't yet become the "Fifth Avenue" advertisement it turned into later. In the pilot, these women look like they actually work for a living. Miranda is in corporate suits that are a little too big. Carrie’s apartment looks small and—dare I say—slightly cluttered and realistic for a columnist’s budget. It was only as the show became a massive hit that the "labels" started to take over the narrative. In the beginning, it was just about the talk.
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And the talk was dirty.
HBO gave them the freedom to say "the word." You know the one. They talked about anatomy, positions, and disappointment with a frankness that literally didn't exist anywhere else on the dial. Friends was on NBC at the same time, and while that show was great, it was sterilized. Sex on Friends was a plot point; sex in the first episode Sex and the City was a character.
The "Secret" Character Who Didn't Make the Cut
There’s a lot of trivia surrounding the pilot that most casual fans miss. For instance, the character of Stanford Blatch appears, but he’s not quite the "Stanny" we come to love. The show was still testing the waters of how to portray Carrie’s life outside of the core group.
There’s also the fact that the pilot was actually filmed months before the rest of the series. If you look closely at Sarah Jessica Parker’s hair, it changes texture and color between the first and second episodes. In the pilot, it's a darker, more natural brown-blonde. By episode two, the "honey blonde" highlights that defined the late 90s started to creep in.
The episode ends with a moment that defines the "single girl" era. Carrie is in a car with a guy she’s supposed to have "sex like a man" with. She realizes she can’t do it. She wants the "zip." She wants the feeling. She gets out of the car, walks home, and the narration kicks in. It’s the realization that while the rules of dating had changed, the human heart hadn't caught up yet.
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Lessons from 1998 That Still Apply
Watching the first episode Sex and the City today is a lesson in cultural evolution. We see the birth of the "toxic relationship" discourse. We see the beginning of the "hustle culture" for creative freelancers in New York.
What can you actually take away from revisiting this pilot?
First, look at the career trajectory. Carrie wasn't an icon yet; she was a struggling writer with a niche column. It’s a reminder that every "overnight success" starts with a messy, unpolished first draft. The pilot is that first draft. It’s got flaws, the pacing is a bit weird, and the "talking to the camera" bit is annoying. But the soul was there.
Second, the friendship dynamic was the only thing that didn't need "fixing." Even in the pilot, the way the four women sit around a table and dissect their lives feels authentic. It was the first time television portrayed female friendship not as a secondary plot to a romance, but as the primary romance of a woman's life.
If you’re a fan, go back and watch it tonight. Ignore the grainy film stock. Ignore the weird interviews. Focus on the moment Carrie sees Big for the first time. It’s a masterclass in how to set up a series-long arc in under thirty seconds.
Next Steps for the Superfan:
- Audit the Pilot: Rewatch the first ten minutes and count how many times Carrie looks at the camera. It happens more than you think.
- Compare the Apartment: Look at Carrie’s apartment in the pilot versus the movie. The layout is actually different; the kitchen area underwent a massive change once the show got picked up for a full season.
- Track the Evolution: Notice how Miranda’s cynicism is treated as a flaw in the pilot, whereas by the end of the series, it’s her superpower.
The show eventually became a caricature of itself—the movies and the And Just Like That reboot proved that—but that first half-hour in 1998 was lightning in a bottle. It wasn't about the shoes yet. It was about the search for connection in a city that often feels like it's designed to keep you lonely.