25 of the Best Sex and the City Guest Stars
I couldn't help but wonder, who hasn't been on SATC?
Bradley Cooper (Season 2)
Jack (Bradley Cooper) was bad news from the beginning. As Carrie says in the episode, "They Shoot Single People, Don't They?" Jack was everything she needed at 2 a.m. on a Tuesday at a gay bar: single, straight, smoker. It could've been the greasy hair, the tempting smoking habit (she was trying really hard to quit), or the fact that Jack later discovered Carrie's "Single & Fabulous?" New York Magazine cover story — the two never did anything more than make out in a crowded bar and briefly, in his convertible.
Jennifer Coolidge (Season 6)
In "The Perfect Present," Carrie, Samantha, Charlotte, and Miranda head to a purse party thrown by the recently dumped Vanessa, played by the queen of the bend-and-snap. "Isn't life funny? Because of that fucker, I've discovered, I'm Fendi!" she says in the episode, moments before walking into Samantha and Smith (in his pre-Gus Van Sant days) boning against several glass racks.
Geri Halliwell (Season 6)
Geri Halliwell played Phoebe, someone Samantha runs into on one of the hottest days of the summer. While fanning herself, Samantha learns (via Phoebe) that the pool at Soho House is the place to be, that is, if you can get past the waiting list. Enter: Annabelle Bronstein, whose membership card Samantha finds in the bathroom and uses a few times before her jig is up.
David Duchovny (Season 6)
Between the end of The X-Files (the OG run) and the beginning of Californication, David Duchovny guest starred on several TV shows including Sex and the City. He played Jeremy, Carrie's high school boyfriend (sorry, "sweetheart") who completely sweeps her off her feet before revealing he's starting treatment at a mental institution in Connecticut. Here he is welcoming Carrie to the Juneau Spears Center, a place harder to get into (and out) of than the Soho House.
Justin Theroux (Season 1 and 2)
Justin Theroux had the distinct honor of guest starring on SATC twice. On the season one episode, "The Monogamists," Justin played Jared, a writer friend of Stanford's who had a thing for giving the thumbs-up and was named one of New York Magazine's "30 Coolest People Under 30." His character didn't venture too far in the occupation department the second time around; on the season two episode "Shortcomings," Justin played Vaughn, a fiction writer who orgasms too fast (hence, the episode's title).
Elizabeth Banks (Season 3)
In the same episode where Samantha famously said, "I don't believe in the Republican party or the Democratic party; I believe in parties," Elizabeth Banks checked off one of her very first TV roles. In "Politically Erect," Elizabeth played Catherine, the pearl-wearing fiancée of a politician Charlotte had set her eyes on at a fundraiser. According to Catherine, she met Bob, the fiancée, at a party where women brought guys they didn't want to date, leading a martini-filled Charlotte to mumble something about one women's trash becoming another's treasure.
John Slattery (Season 3)
John Slattery played politician Bill Kelley, who was running for city treasurer and famously told Carrie, "I love making love with you," before asking her to pee on him in the shower. When Carrie offered to "dribble warm tea" on him instead, Bill dumped her, citing that his campaign advisors didn't like her sex column. This of course, led Carrie to write a bit called, "To Pee or Not To Pee?" without using his real name. "It was much more political not to," she said on the episode.
Jon Bon Jovi (Season 2)
Reason #2409 why you should never date someone you meet at your therapist's office: Seth, played by Jon Bon Jovi in "Games People Play." In the episode, Seth takes Carrie out to dinner, plays a sexy game of Twister, and tells her he's in therapy because he's "really fucked up about women… after I sleep with them I lose interest" — after sleeping with Carrie.
Sarah Michelle Gellar (Season 3)
In the L.A.-set episode, appropriately titled "Escape From New York," SMG played Debbie, the "most ambitious and feared creature," according to Carrie. Debbie was a junior development executive who really, really wanted to make a movie out of Carrie's columns. She also predicted that the movie would be "chick flick big" before declaring that the man who came up with that term "should have his balls cut off."
Matthew McConaughey (Season 3)
In the same L.A. episode as SMG, Matthew McConaughey played a hyper version of himself who was interested in Carrie's movie and her columns. In a cringe-worthy business meeting, the SATC version of Matthew declared that he wanted to play Mr. Big and sleep with Carrie, all while biting on a toothpick. "We are animals, men, women, walking the earth," he said in this scene. "We are made of head, heart, and loins. We're talking about using them, am I right?" Nah. Carrie was good, which is why she GTFO of there.
Chandra Wilson (Season 5)
Before she was Bailey on Grey's Anatomy, Chandra Wilson played a cop who confronted Samantha about her Richard "CHEATER" posters in the episode titled "Anchors Away." When Samantha explained, "This man said he loved me, and I caught him eating another woman's pussy," the extremely understanding cop backed off in full support of this public shaming.
Molly Shannon (Season 5)
Carrie's columns never did turn into a movie, but they did turn into a book thanks to the brains of Lily Martin, book agent, played by Molly Shannon. Together with Courtney Masterson (Amy Sedaris; see next slide), Lily transformed Carrie's words into something with a spine. At their first meeting, Lily got right to the point: "Is it hopeful? What's the message? What's your point of view, after all the break ups and disappointments and train wrecks? You still believe he's out there, right?" That gasp you heard? Millions of people asking why after all these years, Lily still knows what they're thinking.
Amy Sedaris (Season 5)
When she was not finishing Lily's sentences, Courtney (Amy Sedaris) was busy introducing future lovers to each other. Case in point: Carrie and Berger, who met while Carrie was in a book meeting with Courtney at her office. Hard to believe this relationship eventually ended with a Post-it note by way of The Hamptons, motorcycle rides, and a white noise machine that only took Carrie to the rainforest.
Eddie Cahill (Season 3)
Before he was Tag on Friends, Eddie Cahill played Sean, Carrie's bisexual "generation-something else" fling that she met at a party celebrating his "internet magazine… that I still couldn't find on my computer." Carrie Bradshaw and her internet talk! Despite the fact that they had a great time on her ice skating date (she smoked and drank on the ice like a rebellious young!) Carrie was not prepared for where he took her to next: a party attended by the next SATC guest star on this list...
Alanis Morissette (Season 3)
... Alanis! On "Boy, Girl, Boy Girl.." the Canadian singer played Dawn, who kisses Carrie in a game of spin the bottle. Following the experience, which "wasn't bad, kind of like chicken," Carrie went home and confirmed that she was indeed "too old to play this game." Other than Carrie's giant flower brooch (which of course got an update in one of the movies), this kiss was a shining moment for the episode.
Andy Cohen (Season 6)
To give back, Charlotte volunteered to be a guide for the blind on season six. Part of her training required walking in public with a mask and a guide to experience what the blind experience. Enter: Carrie, who fails miserably as Charlotte's guide. I guess this is why you shouldn't perform these training exercises at a Barneys, especially with stellar shoe salesmen like this one, played by SJP's real-life BFF Andy Cohen, around.
Kat Dennings (Season 3)
There was no one better than Kat Dennings for the role of Jenny Brier, a bratty, lip-gloss wearing 13-year-old who asks Samantha to plan her Bat Mitzvah on season three. When Samantha hesitates, Jenny name drops Carson Daly and "The Clintons" (who "of course can't make it") before casually revealing her bank account: "We'd be lucky if we can swing this for under a mil." To which Samantha responds, "We'll never get *NSYNC."
Bobby Cannavale (Season 3)
On an episode titled "Easy Come, Easy Go," Samantha has a fling with Adam, a director who has well, funky spunk. When he says she's just trying to avoid blowjobs and that they're "easy," Samantha, arguably the best sex-ed teacher (and life coach) on TV, launches into one of the most memorable SATC speeches: "I love giving head. Easy? You men have no idea what we're dealing with down there. Teeth placement, jaw stress, suction, gag reflex, all the while bobbing up and down trying to breathe through our noses. Easy? Honey, they don't call it a job for nothing." Mic. Drop.
Margaret Cho (Season 4)
On season four, Margaret Cho played Lynne, a fashion show producer who recruits Carrie to walk in a show that features New Yorkers and models alike. "No one is more New York or has more style than you," she says on the episode, "The Real Me." When Carrie hesitates, Lynne delivers another convincing command: "You're fucking doing my show. If I have to hunt you down, skin you alive, and have one of the models fucking wear you." The only problem with this character was that there was not enough of her. Imagine her having a showdown with Samantha?
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