It was 1998. New York looked different. The lighting was grainier, the cigarettes were everywhere, and the Sex and the City cast season 1 didn't yet know they were about to rewrite the rules for how women talked on television. Honestly, looking back at those early episodes, it feels like a different show entirely. It’s grittier. It’s almost a mockumentary at times. Carrie Bradshaw, played by Sarah Jessica Parker, keeps breaking the fourth wall to talk to us directly, staring right into the lens like she’s trying to figure out if we’re as confused about dating as she is.
Most people forget that the first season was basically an experiment. Darren Star, fresh off the massive success of Melrose Place, took Candace Bushnell’s New York Observer columns and tried to turn them into something that felt real. Not "TV real," but "New York 3:00 AM" real. The casting was everything. If you swap out even one of those four women, the whole thing collapses.
The Core Four: Who They Actually Were in 1998
When we talk about the Sex and the City cast season 1, we have to start with Sarah Jessica Parker. She wasn't the fashion icon yet. In 1998, Carrie Bradshaw was a writer who lived in a cramped, cluttered apartment and wore outfits that looked like she’d found them in a thrift store—because she had. SJP brought this jittery, nervous energy to the role that made the character relatable. She was the anchor.
Then there’s Kim Cattrall as Samantha Jones. It’s wild to think Cattrall almost turned the role down multiple times. She was older than the other girls, and that mattered. She brought a level of confidence that felt dangerous for late-90s TV. Samantha wasn't just "the slutty friend"—a lazy label people used back then. She was a PR powerhouse who refused to apologize for having a libido. In season 1, she’s a bit more cynical, a bit harder around the edges than she became in later years.
Cynthia Nixon was a Broadway veteran when she was cast as Miranda Hobbes. People forget Miranda was the only one with a real, high-pressure corporate job in that first year. She was the cynical voice of reason. While Carrie was romanticizing every guy she met at a gallery opening, Miranda was pointing out that they were all probably married or emotionally stunted.
And Kristin Davis. Charlotte York. She was the "Pollyanna" of the group, but in season 1, her quest for the "Old Maid" marriage was treated with a bit more bite. She wasn't just a ditz; she was a woman with a very specific, traditional plan in a world that was rapidly moving away from tradition.
Supporting Players Who Defined the Era
You can't discuss the Sex and the City cast season 1 without mentioning Chris Noth as Mr. Big. He wasn't even supposed to be the "one." He was just a guy Carrie bumped into in the pilot. But the chemistry? It was immediate. Noth played Big with this untouchable, Sinatra-esque cool that made it perfectly clear why Carrie would lose her mind over him for the next decade.
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Then there's Stanford Blatch. The late Willie Garson was Carrie’s "fifth lady." In the first season, his role was vital because he gave Carrie a life outside of the core group. He was her connection to the underground, the messy, and the fabulous.
We also saw early appearances from Ben Weber as Skipper Johnston. Remember Skipper? He was the "nice guy" who served as a foil to the wolves Carrie was usually dating. His presence in season 1 is a reminder of how much the show was originally about the diversity of dating experiences, rather than just the high-fashion glam it became.
What Most People Get Wrong About Season 1
A lot of fans jump straight to season 3 or 4 when they do a rewatch. They want the Dior saddles and the Aidan drama. But if you skip the Sex and the City cast season 1, you miss the foundation.
- The "Man on the Street" Interviews: Season 1 featured real (and scripted) New Yorkers talking to the camera. It felt like a sociology project.
- The Fashion: It was accessible. No one was wearing head-to-toe couture yet. Carrie wore a lot of simple slip dresses and weird vintage coats.
- The Cinematography: New York looked blue, cold, and a little bit dirty. It wasn't the postcard version of the city we saw in later seasons.
The show was actually quite dark. It dealt with the loneliness of being single in a way that later seasons sometimes glossed over with a montage of shoe shopping. The cast had to ground that darkness. If Kim Cattrall hadn't played Samantha with such warmth, the character would have been a caricature. If Cynthia Nixon hadn't played Miranda with such intelligence, she would have just been "the angry one."
The Pivot Points of the First 12 Episodes
The first season is only 12 episodes long. That’s it. In that short span, the Sex and the City cast season 1 had to establish a shorthand that made us believe these women had been friends for years.
Take the episode "Models and Mortals." It tackles the insecurity women feel when compared to the "beautiful people" of Manhattan. The cast handled it with a mix of humor and genuine pathos. When Carrie feels inferior to the model Big is dating, SJP doesn't play it for laughs; she plays it for the sting.
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Then you have "Three's a Crowd," where the show really started pushing boundaries on what could be discussed on cable. The chemistry between the four leads during the brunch scenes—which became the show's signature—was already locked in. You can't fake that kind of rapport. It’s either there or it isn’t.
Why the Casting Director Deserves More Credit
Jennifer Euston and the team behind the scenes had a monumental task. They weren't just looking for actresses; they were looking for archetypes that didn't feel like stereotypes.
They needed a Carrie who could be neurotic but still someone you’d want to grab a drink with. They needed a Samantha who was predatory but likable. The Sex and the City cast season 1 worked because the actors brought a level of "Thespian" weight to what could have been a very fluffy show.
Kristin Davis, for instance, came from a soap opera background (Melrose Place), but she played Charlotte with a nuanced vulnerability. She wasn't just a "Preppy"; she was a woman who genuinely believed in the fairy tale, even when the evidence was stacked against her. That's a hard needle to thread.
The Cultural Impact Nobody Expected
When the pilot aired on June 6, 1998, the critics were mixed. Some thought it was too raunchy. Others thought it was too cynical. But the audience—specifically women—saw themselves.
The Sex and the City cast season 1 gave voice to the "secret" conversations women were having. It validated the idea that being 30-something and single wasn't a tragedy; it was an adventure. Or, at the very least, it was a really good story to tell your friends over eggs Benedict the next morning.
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The show also changed the way New York was portrayed. It wasn't the "Friends" version of New York where everyone has a giant apartment and no one seems to work. The season 1 cast showed the hustle. Carrie’s bus ads, Samantha’s PR events, Miranda’s late nights at the firm—it felt like a city where people actually had to pay rent.
Assessing the Season 1 Legacy
Looking back, the Sex and the City cast season 1 was the most honest the show ever was. Before the fame, before the movies, and before the reboot, it was just four women in a city that didn't care if they succeeded or failed.
The actors were hungry. You can see it in their performances. They were taking risks. Sarah Jessica Parker’s performance in the first season is arguably her best work because she hadn't yet become the "icon." She was just an actor trying to find the heart of a messy character.
What to Look for on Your Next Rewatch
If you’re going back to watch the first season, pay attention to the background characters. You’ll see early roles from people like Bradley Cooper (season 2, but the vibe starts here) and other New York stage actors who went on to become huge stars.
Also, watch the body language between the four leads. In the first few episodes, they are still "finding" each other. By the season finale, "Oh Come All Ye Faithful," they move as a unit. The bond is real.
Moving Forward: How to Appreciate the Origins
To truly understand the phenomenon, you have to strip away the "And Just Like That" baggage. Forget the off-screen feuds. Forget the million-dollar wardrobes.
- Watch the Pilot Again: Notice how the characters talk to the camera. It’s a relic of a style the show eventually abandoned, but it’s fascinating.
- Focus on the Dialogue: The season 1 scripts were heavily influenced by Bushnell’s actual prose. It’s sharper and more biting than the later, more sentimental seasons.
- Appreciate the New York Scenery: Before the show became a tourist attraction, it filmed in real, gritty locations that gave it an authentic "East Village" feel.
The Sex and the City cast season 1 didn't just play characters; they defined a generation's view of friendship. They proved that the most important relationship you have is the one with yourself—and the people who help you pick up the pieces when the "Mr. Bigs" of the world let you down.
For those looking to dive deeper into the history of the show, checking out the original HBO archives or reading Candace Bushnell’s initial columns provides a stark contrast to how the characters evolved. The evolution from the 1998 cast to the modern-day iteration is a masterclass in how television branding changes over decades. Stick to the early episodes if you want the truth; watch the later ones if you want the dream. Both have their place, but the foundation was built in that first, messy year.