If you’re marathoning Sex and the City for the tenth time, you might start seeing double. No, it’s not the third Cosmopolitan kicking in. It's actually a weird piece of TV history that mostly happens in the background of the late '90s.
Justin Theroux on Sex and the City isn't just a guest appearance. It's actually two. He played two completely different men who both tried (and failed) to woo Carrie Bradshaw in the span of about a year.
It’s the ultimate "wait, wasn't he just here?" moment. Back in the day, before social media could scream about continuity errors in real-time, shows used to do this kind of thing. They’d find an actor they loved and just... bring them back as someone else. Honestly, if you weren't paying close attention to the credits, you might have missed it entirely because of a very strategic haircut.
The Jared Phase: 1998’s Most Egotistical Writer
The first time we see Justin Theroux is in Season 1, Episode 7, titled "The Monogamists." He plays a guy named Jared.
Jared is basically the personification of everything annoying about the New York literary scene in the '90s. He’s an author. He’s "cool." He’s one of those guys who probably spent too much money on shark-tooth necklaces and leather vests. Stanford Blatch introduces him to Carrie at a bar, bragging that Jared was named one of the "30 Coolest People Under 30" by New York Magazine.
He’s smarmy. That’s the best word for it. He flirts with Carrie, but it’s the kind of flirting that feels like he’s actually just flirting with himself in a mirror.
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Carrie, being Carrie, uses him. She’s trying to make Mr. Big jealous, so she brings Jared to a party. He’s essentially a human prop. He’s there to look edgy and successful so Big will notice her. Once the episode ends, Jared vanishes into the ether of Manhattan, presumably to go talk about his book sales to someone else.
The Vaughn Wysel Rebrand: Short Hair, Big Shortcomings
Flash forward to Season 2, Episode 15, "Shortcomings."
Suddenly, Theroux is back. But this time, he’s not Jared. He’s Vaughn Wysel. If Jared was the "bad boy" writer, Vaughn is the "sensitive" one. He’s a short-story writer. He wears wire-rimmed glasses and, most notably, a very tight buzz cut.
Carrie is actually into him. Like, really into him. But as the episode title suggests, things aren't perfect. While Jared was an ego-maniac, Vaughn’s problem is much more... physical. He struggles with premature ejaculation. It’s one of those classic Sex and the City storylines where a guy is great on paper but has one specific, glaring issue that makes the relationship impossible.
What’s wild is how much Carrie loves his family. She meets his mother, Wallis (played by the legendary Valerie Harper), and his sisters, and she basically wants to move in with them. She’s more heartbroken about breaking up with his family than she is about leaving Vaughn.
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Why the double casting happened
People often ask how this happened without anyone noticing. Justin Theroux eventually cleared it up in an interview with PeopleTV. Basically, the show "burned through" every eligible male actor in New York City pretty quickly.
The producers liked him so much they wanted him back. Their high-tech solution for the identity crisis? "We’ll just shave your head."
That was it. That was the whole plan. They figured if they cut his hair and put some glasses on him, the audience wouldn't realize it was the same guy who was hitting on Carrie six months prior. To be fair, for a lot of people, it worked.
The "Recycled Actor" Club
Theroux isn't the only one who did a double-take in the SATC universe. It's actually a bit of a pattern.
- André de Shields: He was a tap dancing instructor in the original series and then showed up as a law professor in And Just Like That.
- Peter Hermann: He played a guy Charlotte flirted with in Season 6 and then returned as the software engineer who dates Carrie in the reboot.
- Andy Cohen: He had two cameos—once as a guy at a gay club and once as a shoe salesman.
It makes the show feel a little bit like a small town, despite being set in the most populous city in the country. It’s sort of charming, in a low-budget-theater-troupe kind of way.
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Why it still feels authentic
Even with the weirdness of seeing the same face twice, Theroux’s performances hold up. He plays Jared with a greasy, over-the-top confidence that makes you want to roll your eyes. Then he turns around and plays Vaughn with a vulnerability and anxiety that is actually kind of heartbreaking.
He managed to play two different versions of the "New York Intellectual" and made them feel like distinct humans. One was a guy you’d avoid at a party; the other was a guy you’d try to make it work with even when it clearly wasn't going to happen.
If you’re looking to spot these appearances yourself, you don't need a detective's kit. Just look for the guy who looks like he belongs on the cover of a '90s indie rock album.
What to do next
If you want to catch the full "Theroux Experience" in the SATC world, here is exactly where to look:
- Watch "The Monogamists" (Season 1, Episode 7): Look for the long hair and the shark-tooth necklace. Pay attention to how he interacts with Stanford.
- Watch "Shortcomings" (Season 2, Episode 15): Note the buzz cut and the glasses. Compare his body language to his Season 1 appearance.
- Check out his screenwriting: Since he played so many writers on the show, it's fun to see what he actually wrote in real life, like Tropic Thunder or Iron Man 2.
Seeing the transition between these two roles is a great reminder of how much "The City" actually functioned as a training ground for actors who were about to become huge stars. For Theroux, it was just a pit stop on the way to Mulholland Drive and The Leftovers, but for fans, it remains one of the best "Easter eggs" in the entire series.