9 Sex and the City Cameos You May Have Missed

by Ashley Morton

Timothy Olyphant, Kat Dennings and David Duchovny are just some of the faces to keep an eye out for while rewatching the award-winning series.


Going back to rewatch Sex and the City is fantastic for a number of reasons: the throwbacks (remember when Carrie learned how to “chat” online?); the fashion (the trends the show started, and the ones that have since come back), and, of course, the great stories of female empowerment (Miranda buying her own apartment).

Another great reason: A game of “where are they now?” Sex and the City is chock-full of one-episode walk-ons by actors who, at the time, may have flown under your radar. Here’s a list of our favorites from across the show’s six seasons.

1. Bradley Cooper as Jake

Season 2, Episode 4: They Shoot Single People, Don’t They?

One of Oscar-nominee Bradley Cooper’s first credited roles was as the jerk who laughingly (and probably unintentionally) calls into question Carrie’s lifestyle. The moment Jake smacks that “Single and Fabulous?” magazine cover on the window of his hot red car brings up a flood of questions the show’s characters had been avoiding, for obvious reasons.

2. Justin Theroux as Jared, and Vaughn Wysel

Season 1, Episode 7: “The Monogamists”

Season 2, Episode 15: “Shortcomings”

Before he was troubled police chief Kevin Garvey on The Leftovers or even French-horn player Joe on Six Feet Under, Theroux took not one, but two turns on SATC. How to tell them apart? Vaughn’s head is shaved. That’s not to say the characters aren’t also widely distinct from one another — Jared is the confident stranger Carries uses to make Big jealous, and Vaughn is a talented short-story writer, who coincidentally, doesn’t last long in bed. Maybe it’s odd to have the actor in two roles on the same series, but really, who could be upset about a double dose of Theroux?

3. Bobby Cannavale as Adam Ball

Season 3, Episode 9: “Easy Come, Easy Go”

Since his appearance on Sex and the City, Cannavale has become an HBO heavy-weight, with roles on Oz, Six Feet Under, Boardwalk Empire and Vinyl. But back in 2000 he was simply the guy with the “funky tasting spunk” who Samantha refused to pleasure. When he tries to convince her it isn’t such a big deal, she walks him through the task as if she’s giving a speech on women’s rights. To quote her, “Honey, they don’t call it a job for nothing.”

4. Kat Dennings
as Jenny Brier

Season 3, Episode 15: “Hot Child in the City”

But really, is there a difference between 13-year-olds and 30-somethings? That’s the big question this episode tries to answer, when Miranda gets braces and has issues with mean girls, and Samantha is hired to throw a party for teenager Jenny Brier. Jenny and her friends dress like, talk like, and act like Sam and co., and it makes all of the women wonder if they’ve grown up at all. It’s fun to watch Dennings, in her first credited role, face-off against the confident Kim Cattrall, and think about all of the sass we’ll see from her in the future.

5. Timothy Olyphant as Sam

Season 1, Episode 4: “Valley of the Twenty-Something Guys”

Still working his way up the Hollywood ladder (and several years before a starring role in Deadwood), Olyphant appeared as Sam, the 20-something guy whose vortex of great kissing and no-need-for-a-last-name sucks Carrie right in. The true highlight of his performance is when he attempts to describe a dream he had — complete with giant hands and Carrie as a “unicorn woman” (she doesn’t know what that means either). Unkempt, unconcerned, and cute as hell, Sam is an amusing rewatch not only for the cameo but also for the memories of what it was like dating in your 20s.

6. Alanis Morissette as Dawn

Season 3, Episode 4: “Boy, Girl, Boy, Girl...”

What better opportunity for a cool guest star than when Carrie Bradshaw kisses a woman for the first time? Morissette, fresh off of playing God (Dogma), and Sarah Jessica Parker wind up locking lips in a game of spin the bottle that Carrie plays with her bi-sexual boyfriend (Eddie Cahill) and his friends. Carrie’s head whirls at the prospect of dating a man who sleeps with both men and women, a topic rarely discussed on television back when the episode originally aired, making this one especially worth the rewatch. Morissette’s celebrity presence is a little hard to overlook, but still very welcome, even if Carrie freaks out and decides it’s all a bit too fluid for her.

Bonus: If you like musician cameos, also keep a look out for Jon Bon Jovi in Season 2, Episode 13, “Games People Play.”

7. Sarah Michelle Gellar as Debbie

Season 3, Episode 13: “Escape from New York”

Sarah Jessica Parker meet Sarah Michelle Gellar. Matching Sarah-triple-nomenclature aside, Geller’s role as a fast-talking L.A. junior exec is just fabulous. Carrie’s inability to keep up, and Debbie’s insistence that they are the same (which makes the name thing even better) is a glorious introduction to the Los Angeles pace that Carrie struggles to navigate for the rest of the episode. Like any visit to Hollywood, keep an eye out for other celeb sightings like Vince Vaughn, Carrie Fisher and Matthew McConaughey.

8. David Duchovny as Jeremy

Season 6, Episode 10: “Boy, Interrupted”

When it was announced that David Duchovny would be on the series, a small part of everyone thought, This is it: Carrie was going to settle down with a boy she once dated in high school. But the series pulled a big 180 and it turned out Jeremy had some things to work through, which drove him straight to the asylum. Even if Jeremy was doing what all New Yorkers should try once in a while (self-reflection!), it wasn’t on par with what Carrie was looking for, and the two went their separate ways.

9. Gabriel Macht as Barkley

Season 1, Episode 2: “Models and Mortals”

No list would be complete without a throwback to the early days, when guest stars were still speaking straight to camera, and each of Carrie’s columns were front and center. Gabriel Macht plays an artist whose main passion isn’t painting, but hanging around in his birthday suit with gorgeous women. This early episode, and Barkley’s unabashed preference for sleeping with models, is the perfect frame for introducing Carrie’s friends: Miranda is disgusted, Charlotte wants to fix herself, and Samantha declares she’s just as attractive as a model and decides to sleep with Barkley. The premise is the perfect kick-off to how these women perceive themselves and the world around them, and it’s a worthwhile rewatch to see how things evolve by Season 6.

This list is just the beginning: Go back and watch the entire series to see how many other guest stars you can catch, including Sarah Jessica Parker’s Divorce co-stars Molly Shannon and Dean Winters, John Slattery as a guy who puts the “pee” in politician, True Blood’s Carrie Preston, and more.

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