We all remember the shoes. The Cosmopolitans. The puns about Post-it notes. But when you rewatch the original HBO run today, the most shocking thing isn't Carrie Bradshaw’s questionable financial choices—it’s the faces. Sex and the City guest stars make up a literal "who’s who" of Hollywood's elite, many of whom were basically nobodies when they walked onto the New York set.
It’s wild.
Think about it. Before he was an Oscar nominee, Bradley Cooper was just a guy in a convertible looking for a party. Before Justin Theroux was a prestige TV heavyweight, he played two entirely different characters on the same show. The casting directors, Jennifer Euston and Alexa Fogel, weren't just filling roles; they were accidentally building a time capsule of future A-listers.
The One Where Bradley Cooper Was Just "Jake"
In the episode "They Shoot Single People, Don't They?", Carrie is reeling from a disastrous New York Magazine cover photo. She’s looking for a win. She finds it—briefly—in a guy named Jake. That guy was Bradley Cooper. He had hair that was a bit too "late 90s boy band" and a sports car that Carrie eventually forced him to drive to a 24-hour pharmacy so she could see her own face on the newsstand.
It was Cooper’s first-ever screen credit. Honestly, he doesn’t have much to do other than look handsome and smoke a cigarette, but the charisma is already there. You can see the movie star DNA even when he's playing second fiddle to a magazine layout. He’s one of the most famous Sex and the City guest stars now, but back then? He was just a kid from Philly getting his SAG card.
Matthew McConaughey and the Meta-Moment
Then there’s the Hollywood episode. "Escape from New York" is a fever dream of cameos. But Matthew McConaughey playing a hyper-caffeinated, slightly unhinged version of himself is the peak.
He wasn't the first choice.
The producers actually wanted Alec Baldwin. He passed. Then they went to George Clooney. He was busy. Warren Beatty? No dice. McConaughey stepped in and turned what could have been a standard "star plays himself" moment into something bizarre and memorable. He’s wearing a cowboy hat. He’s yelling about the script for Carrie’s column. He’s vibrating with an energy that makes Carrie—and the audience—deeply uncomfortable. It’s brilliant because it mocks the very industry the show was currently conquering.
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The Double Feature: Justin Theroux
Most shows try to hide it when they reuse actors. Sex and the City didn’t care. Justin Theroux appears in Season 1 as a slick guy named Jared. He’s "cool." Then, in Season 2, he comes back as Vaughn Wysocki, a short-story writer with a lovely family and a very specific, very premature physical problem.
He played both roles with such different energy that half the audience didn't even realize it was the same guy. That’s the thing about these guest spots; they were often character studies rather than just "eye candy" roles. Theroux’s second turn as Vaughn is actually a really grounded, albeit awkward, look at sexual incompatibility. It wasn't just a gag. It felt like a real, albeit brief, relationship.
When Indie Icons Met the Upper East Side
The show had a weird knack for picking actors who would go on to define "Prestige TV" a decade later.
Take Elizabeth Banks. She shows up for about thirty seconds as a woman named Catherine who is frustrated by an impotent politician. She has maybe three lines. Or Sarah Paulson, who plays Carrie’s sister-in-law in a plotline about a "secret" pregnancy. Paulson is now the queen of Ryan Murphy’s universe, but in Season 1, she was just a guest star providing a foil for Carrie’s neuroses about motherhood.
And we can't forget John Slattery.
Before he was Roger Sterling on Mad Men, he was Bill Kelley, the politician with a very specific "golden" fetish. Slattery played it with this smooth, silver-fox charm that made the eventual reveal—that he wanted Carrie to, uh, relieve herself on him—genuinely jarring. It’s one of those Sex and the City guest stars moments that people still talk about because it pushed the boundaries of what cable TV was allowed to show (and talk about) in the year 2000.
The Comedians Who Just Wanted a Piece of the Action
A lot of people forget how many stand-up legends and comic actors cycled through the show.
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- Vince Vaughn: Played Keith Travers, a guy pretending to be Matt Damon's agent in LA. He was peak "fast-talking Vince" here.
- Will Arnett: Played a guy Samantha dates who likes to... have sex in front of his parents. Yeah, it was weird.
- Kat Dennings: She was literally 13 or 14, playing a bratty Bat Mitzvah client for Samantha. She held her own against Kim Cattrall, which is no small feat.
- Bobby Cannavale: He played "Adam with the funky tasting spunk." A role that, frankly, most actors would have turned down, but he leaned into the absurdity of it.
The show worked because it treated these guests like real New Yorkers. They weren't just props. Even the "freaks of the week" had layers. They represented the endless, exhausting cycle of dating in a city of millions. Every time Carrie or Miranda sat across from a new guy, the audience was meeting someone new, too. Often, it was someone we’d be seeing on award stages ten years later.
Why the Guest Stars Mattered for SEO and Status
Let's get technical for a second. The show didn't just need bodies; it needed vibe.
Using established New York theater actors like Nathan Lane or Marian Seldes gave the show "uptown" credibility. Bringing in LA stars like David Duchovny (playing Carrie’s high school sweetheart who is committed to a mental institution) gave it "mainstream" power.
Duchovny was at the height of his X-Files fame when he appeared. It was a massive get. His character, Jeremy, was soft and vulnerable—the polar opposite of Fox Mulder. It showed that Sex and the City was a place where "serious" actors could come to play against type. It wasn't just a "chick flick" show; it was a high-status destination.
The Surprising Legacy of the Small Roles
Sometimes the biggest impact came from the smallest roles. Geri Halliwell (Ginger Spice) showed up as a woman Samantha meets at the Soho House pool. It was a tiny cameo, but it signaled the show’s global reach. If a Spice Girl wanted to be on your show just to talk about how hot it was outside, you’d officially made it.
Then there’s Lucy Liu. She played herself in a plotline about a Birkin bag. It’s one of the most iconic episodes because it blended celebrity culture with the show's obsession with luxury goods. It wasn't just a guest appearance; it was a plot engine.
How to Spot Future Stars in Your Rewatch
If you’re going back through the series now, pay attention to the background.
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- Watch the eyes. Actors like Chandra Wilson (pre-Grey’s Anatomy) or Tony Hale (Veep) appear in tiny roles—a police officer, a caterer—and they bring a level of professionalism that makes the world feel lived-in.
- Look for the "types." The show loved a "type." The "Latvian model," the "Short-Story Writer," the "Wall Street Guy." Often, the actors playing these types were actually highly trained Broadway stars.
- Check the credits. Sometimes you’ll see a name and think, "Wait, is that...?" Yes, it usually is.
Actionable Takeaways for Superfans
If you want to dive deeper into the world of Sex and the City guest stars, don't just stick to the highlight reels.
First, look up the work of casting director Alexa Fogel. She has a legendary eye for talent (she also cast The Wire). Understanding her philosophy helps you see why the show felt so grounded despite its flamboyant fashion.
Second, compare the guest stars of the original series to the cameos in the revival, And Just Like That.... Notice the difference in tone. The original series used guests to challenge the main four characters, whereas the revival often uses them for nostalgia or social commentary.
Finally, if you're a trivia buff, track the "double-dippers." Beyond Justin Theroux, there are several actors who played multiple roles across the six seasons. Finding them is like a hidden object game for TV nerds.
The guest stars were the lifeblood of the show’s version of Manhattan. They made the city feel infinite. Every revolving door at a restaurant brought a new face, a new conflict, or a new future Oscar winner. That’s the real magic of the show—not just the clothes, but the people who filled them, even if only for a single episode.
To get the most out of your next rewatch, cross-reference the IMDB pages of the Season 1 "dates" with their current careers; you'll find that the "random guy" Carrie met at a gallery is now likely headlining a series on Netflix or starring on Broadway. It changes the way you view the show's evolution from a scrappy cable experiment to a cultural juggernaut.