It’s June 6, 1998. Bill Clinton is in the White House, "The Boy Is Mine" is blasting on the radio, and HBO—a network then known mostly for boxing and gritty dramas like Oz—decides to air a show about four women talking about their bedposts. Most people forget how jarring that Sex and the City first episode actually was. If you go back and watch it now, it feels like a fever dream. Carrie Bradshaw isn't just a columnist; she’s a breaking-the-fourth-wall investigative reporter. She looks directly into the lens. She talks to us. It’s a documentary style that the show abandoned almost immediately, yet it set the stage for a cultural shift that nobody saw coming.
Honestly, the pilot is a bit of a mess. But it’s a brilliant mess.
We meet Carrie at a birthday party for a friend who is "turning 30 and handles it with the grace of a Kennedy." That’s the vibe. High stakes, high fashion, and a total lack of the polished, cinematic gloss that defined the later seasons. The grain is heavy. The lighting is moody. New York looks less like a postcard and more like a place where you might actually get mugged. This wasn't the "shoes and cupcakes" show yet. It was a cynical, gritty examination of whether women can actually have sex like men.
The "Sex Like a Man" Experiment
The central thesis of the Sex and the City first episode is a question posed by Carrie’s friend, a high-powered producer named Elizabeth: "Why are there so many great unmarried women and no great unmarried men?" It leads to the big experiment. Can women separate emotion from physical intimacy?
Miranda Hobbes is already fully formed here. She’s cynical, brilliant, and tired of the "man-junk." Cynthia Nixon plays her with a sharpness that feels more grounded than the caricature she sometimes became in the later movies. Then you have Charlotte York. Interestingly, in the pilot, Charlotte isn't quite the "Pritchard" we grow to love. She’s a bit more sexually adventurous, or at least open to the idea of the "power lesbian" scene, before the writers pivoted her into the gallery-owning traditionalist.
And Samantha Jones? She enters the frame like a hurricane. She’s the one who truly embraces the "sex like a man" mantra. Kim Cattrall’s performance in this first half-hour is foundational. She isn't just looking for a husband; she’s looking for a Tuesday night.
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Breaking the Fourth Wall
One of the most bizarre elements of the pilot is the "man on the street" interviews. We see random New Yorkers—played by actors, though they feel like real people—complaining about their dating lives. Carrie narrates these segments like she’s hosting a segment on 60 Minutes. This mockumentary style was a direct lift from the source material, Candace Bushnell’s original New York Observer columns.
Darren Star, the creator, clearly wanted to bridge the gap between journalism and fiction. It works, but it’s distracting. You can see why they dropped it. The show's heart wasn't in the statistics of New York dating; it was in the chemistry between the four leads. When they are sitting at that first restaurant table together, the air changes. You realize that the "sex" in the title is the hook, but the "city" and the "friendship" are the actual story.
Enter Mr. Big: The Meet-Cute That Changed TV
You can’t talk about the Sex and the City first episode without mentioning the moment Carrie drops her purse in the middle of a busy Manhattan street. A black town car stops. A man steps out. He’s handsome, he’s wealthy, and he’s incredibly smug. This is Mr. Big, played by Chris Noth.
The name "Mr. Big" was intended to be a joke—a nickname for the kind of "next major tycoon" that dominated the 90s social scene. He was modeled after Ron Galotti, a real-life publishing executive Bushnell dated. In the pilot, he’s mysterious. He doesn't have a name. He’s just a presence. When he tells Carrie, "Ab-so-lutely," after she asks if he’s ever been in love, a million TV tropes were born.
What’s fascinating is how little they actually interact. He’s a specter. He represents the "unreachable man" that the pilot claims women are trying to emulate. It’s a perfect setup. He is the personification of the cold, detached New York bachelor that Carrie thinks she wants to conquer.
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The Fashion: Before the Stylists Took Over
In the later seasons, Patricia Field turned the show into a high-fashion runway. Every outfit was a statement. In the first episode, things are... different. Carrie is wearing a lot of black. She’s wearing a sheer slip dress with no bra. She looks like a real woman who lives in a walk-up apartment and spends too much money on cigarettes and martinis.
The famous tutu from the opening credits? It was a $5 find from a bargain bin. That DIY aesthetic is all over the pilot. It’s less about labels and more about a specific "downtown" energy. It’s raw. It feels authentic to a version of New York that doesn't really exist anymore—the pre-9/11, pre-gentrified, messy Manhattan where you could still find a dive bar that served decent gin.
Why the Pilot’s Cynicism Matters
A lot of modern viewers go back to the Sex and the City first episode and find it "problematic" or "dated." Yes, the lack of diversity is glaring. Yes, the gender politics are binary and sometimes reductive. But you have to view it through the lens of 1998. At the time, Friends was the dominant sitcom. On Friends, sex was a "will-they-won't-they" plot point that took years to resolve.
Sex and the City blew the doors off that. It talked about "modelizers"—men who only date models. It talked about the "secret sex lives" of the elite. It was revolutionary because it allowed women to be messy, selfish, and unrepentant about their desires.
The pilot ends with Carrie going home with a guy she doesn't really like just to see if she can feel nothing. She fails. She realizes that she’s not a "man" in the way the episode defines it. She wants the "zip" and the "zing." She wants the emotion. This realization is the engine that drives the next six seasons. It’s the admission that while the "sex like a man" experiment is a fun theory, it’s not how she’s wired.
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Hidden Details You Probably Missed
If you look closely at the background of the party scenes, you’ll see the real New York of the late 90s. The technology is ancient. Carrie uses a massive beige computer. No one has a cell phone; they use landlines and pagers. This lack of instant connectivity is what makes the dating stakes feel so much higher. If someone doesn't call you back, they are effectively dead to you.
Also, pay attention to Skipper. Remember Skipper Johnston? He’s Carrie’s "nice guy" friend who eventually gets phased out of the show entirely. He represents the sensitive male perspective that the show eventually realized it didn't need. The show worked better when the men were either "conquests" or "obstacles," not part of the inner circle.
The Iconic Intro That Wasn't
The opening credits we all know—Carrie in the tutu getting splashed by a bus—actually appear in the pilot, but the music is slightly different, and the editing feels faster. That bus ad for "Carrie Bradshaw: Two Cents" is the only thing that remains consistent throughout the entire run. It’s the visual anchor of the series. It tells us who she is: a woman whose life is literally being driven over by the city she loves.
Practical Takeaways for Your Next Rewatch
If you’re planning to dive back into the series, don't skip the first episode. It’s the foundation, even if the walls look a little different than you remember.
- Watch for the Fourth Wall: Count how many times Carrie speaks directly to you. It happens more than you think.
- Track the Evolution: Notice how much more cynical the characters are here compared to the more sentimental later seasons.
- Spot the Real NYC: Look for the gritty, unpolished streets that the show eventually traded for high-end boutiques and pristine parks.
- The Big Introduction: Compare your first impression of Mr. Big in this episode to how you feel about him by the series finale.
The Sex and the City first episode wasn't just a pilot; it was a manifesto. It told the world that women’s lives—their friendships, their sexual frustrations, and their professional ambitions—were worthy of a "prestige" television treatment. It changed the way we talk about relationships. It made "The Talk" a global phenomenon.
To get the most out of your rewatch, try to watch the pilot and the series finale back-to-back. The contrast is staggering. You see the growth of the characters, but more importantly, you see how the show itself grew up. It went from a cynical experiment to a love letter to the endurance of female friendship. That journey started with a single drop of a purse on a busy New York street.
Next Steps for Fans:
- Read the Original Column: Pick up Candace Bushnell’s book Sex and the City. It’s much darker and more journalistic than the show, providing context for the pilot's "mockumentary" style.
- Compare the Pilots: Watch the first episode of the revival, And Just Like That..., immediately after the original pilot. The shift in tone, fashion, and social awareness is a fascinating study in cultural evolution.
- Map the Locations: Visit the real-life spots mentioned in the pilot, like the (now closed) restaurants or the general area of Carrie’s first apartment, to see how the neighborhood has changed since 1998.