25 of the most famous guest stars on 'Sex and the City’

Matthew McConaughey, Jennifer Coolidge, and Bradley Cooper on 'Sex and the City'. Photo:
HBO (3)

Sex and the City featured a surprising number of famous guest stars over its six seasons. Now that HBO's seminal comedy is streaming on Netflix, fans who watched the show as it aired in the early-2000s and new viewers alike are discovering just how many recognizable faces appeared in an episode or two. Quite a few popped up as flings for the core four of Carrie (Sarah Jessica Parker), Samantha (Kim Cattrall), Miranda (Cynthia Nixon), and Charlotte (Kristin Davis), while others played exaggerated versions of themselves. Then there were the one-offs any SATC fan will never forget, such as Kristen Johnston and her...rather abrupt exit.

If you couldn't help but wonder who to look out for on your next binge, here are EW's picks for the most famous guest stars on Sex and the City.

01 of 25

Nathan Lane (Bobby Fine)

Sarah Jessica Parker and Nathan Lane on 'Sex and the City'. HBO

Nathan Lane had a memorable appearance in a 2002 episode of Sex and the City. Guest-starring in season 5's "I Love a Charade," Lane played Bobby Fine, a lounge singer who has been friends with Carrie for years. Carrie is in for a surprise when she learns that Bobby is not only straight, but marrying socialite Bitsy von Muffling (Julie Halston) in a big Hamptons wedding.

02 of 25

Kristen Johnston (Lexi Featherston)

Kristen Johnston on 'Sex and the City'. HBO

Kristen Johnston came in and went out with a bang during Sex and the City's sixth season. The 3rd Rock From the Sun star played Lexi Featherston, a former party friend of Carrie's who springs back up in "Splat!," one of the show's final episodes. She runs into Carrie at a party and finds herself camped out by a window when smoking isn't allowed inside the home. She yells, "When did everybody stop smoking? When did everybody pair off? This used to be the most exciting city in the world, and now it's nothing but smoking near a f---ing open window. New York is over. O-V-E-R. Over. No one's fun anymore. What ever happened to fun? God. I'm so bored, I could die," and then does just that when she falls out of said window.

03 of 25

Tony Hale (Tiger)

Jeff Forney and Tony Hale on 'Sex and the City'. HBO

A few years before he became Buster Bluth on Arrested Development, Tony Hale picked up a small role on Sex and the City. He played Tiger, an assistant who helps out a photographer shooting nude pictures for Samantha.

04 of 25

Jennifer Coolidge (Victoria)

Jennifer Coolidge on 'Sex and the City'. HBO

Comedy icon Jennifer Coolidge brought the jokes to "The Perfect Present," a season 6 episode of SATC. The same year that she appeared as Stifler's (Seann William Scott) mom in American Wedding, she played Victoria on the HBO show, a casual friend of the foursome who has recently gone through a breakup. She copes by making outrageous handbags and throws a purse party in an attempt to make some money.

05 of 25

Justin Theroux (Jared/Vaughn Wysel)

Justin Theroux and Sarah Jessica Parker on 'Sex and the City'. HBO

Early in his career, Justin Theroux played two different characters in Sex and the City's first and second seasons. He first took on the role of Jared in season 1's "The Monogamists," playing an author who is friends with Stanford (Willie Garson) and interested in Carrie. Theroux later found himself by Carrie's side once more as Vaughn Wysel in season 2's "Shortcomings." He played an author again, this time one who writes short stories and comes up short in the bedroom with Carrie. Fans remember Vaughn for his charming family, complete with his mother, Wallis (Valerie Harper).

06 of 25

David Duchovny (Jeremy)

David Duchovny and Sarah Jessica Parker on 'Sex and the City'. HBO

Following his turn as Mulder on The X-Files, David Duchovny appeared as Jeremy in "Boy, Interrupted," a season 6 episode of SATC. He played Carrie's high school sweetheart who reconnects with the leading lady in New York City. Their renewed connection is thrown off when Jeremy reveals that he's only in the area because he's been staying in a mental institution in Connecticut.

07 of 25

Vince Vaughn (Keith Travers)

Vince Vaughn played Keith Travers in "Sex and Another City," a season 3 episode in which the ladies travel to Los Angeles. While Keith tells Carrie at a movie premiere that he's there representing Matt Damon, it later comes out that he's actually a personal assistant without all of the real estate and connections he hyped.

08 of 25

Lucy Liu (Herself)

At the height of her Charlie's Angels fame, Lucy Liu played herself in the season 4 episode "Coulda, Woulda, Shoulda." She enters the picture as a potential client for Samantha, but exits soon after when it comes out that Sam dropped Liu's name and was unprofessional when attempting to get her hands on a Birkin bag.

09 of 25

Sarah Michelle Gellar (Debbie)

Sarah Michelle Gellar on 'Sex and the City'. HBO

Doing right by L.A., SATC's two-episode California arc was chock-full of celebrities. Sarah Michelle Gellar appeared in "Escape From New York," the first of the two installments. She played Debbie, a junior development executive who is interested in turning Carrie's columns into a movie.

10 of 25

Matthew McConaughey (Himself)

Matthew McConaughey on 'Sex and the City'. HBO

Joining the L.A. episodes, Matthew McConaughey played himself in "Escape From New York." He appeared in the season 3 episode after Debbie (Gellar) says he's interested in Carrie's potential big-screen adaptation. He sits down with the writer for a meeting, saying of Mr. Big (Chris Noth), "Look at him. He is such a great guy. I mean, I don't know anybody any cooler than Mr. Big. The only question is, really, 'What the f--- is Carrie's problem?'"

11 of 25

John Slattery (Bill Kelley)

John Slattery and Sarah Jessica Parker on 'Sex and the City'. HBO

Long before he was a Mad Man, John Slattery was Bill Kelley, a politician in Sex and the City's third season. He appeared in two episodes, wooing Carrie at a FDNY calendar show in Staten Island before the two parted ways.

12 of 25

Timothy Olyphant (Sam)

Timothy Olyphant and Sarah Jessica Parker on 'Sex and the City'. HBO

One of Timothy Olyphant's very first roles was that of Sam in "Valley of the Twenty-something Guys," a season 1 episode of SATC. He takes on the job of being Carrie's twentysomething guy, spending the night out with her as she mulls over her feelings for Mr. Big.

13 of 25

Alanis Morissette (Dawn)

Alanis Morissette and Sarah Jessica Parker on 'Sex and the City'. HBO

Alanis Morissette locked lips with Carrie as Dawn, a character in season 3's "Boy, Girl, Boy, Girl...". She meets Carrie through Mark, a bisexual man whom Carrie is dating. The two attend the same party, where a game of Spin the Bottle leads to same-sex kisses and a new understanding for Carrie that "gender is an illusion."

14 of 25

Bradley Cooper (Jake)

Bradley Cooper on 'Sex and the City'. HBO

A then-unknown Bradley Cooper picked up his very first acting credit as Jake in "They Shoot Single People, Don't They?" — an episode in Sex and the City's second season. Carrie is feeling insecure after an unflattering magazine shoot, but bumps into Jake on a late night out. While the two initially hit it off, he finds the magazine at a stop for cigarettes and prompts Carrie to leave with his confrontation.

15 of 25

Kat Dennings (Jenny Brier)

A young Kat Dennings was a force to be reckoned with in SATC's third season. In her very first onscreen role, Dennings played Jenny Brier, a 13-year-old girl who enlists Samantha's help in "Hot Child in the City" for an over-the-top bat mitzvah.

16 of 25

Will Arnett (Jack)

Will Arnett made one of his first onscreen appearances in season 2's "La Douleur Exquise!" as Jack. He played a man who is involved with Miranda, but his exhibitionist tendencies become a problem.

17 of 25

Geri Halliwell (Phoebe)

Geri Halliwell on 'Sex and the City'. HBO

Geri Halliwell — a.k.a. Ginger Spice — made a brief but impactful appearance in Sex and the City's sixth season. In "Boy, Interrupted," she played Phoebe, a friend who runs into Samantha on the street and encourages her to join the SoHo House.

18 of 25

Jim Gaffigan (Doug)

Jim Gaffigan and Cynthia Nixon on 'Sex and the City'. HBO

Comedian Jim Gaffigan picked up a gig as Doug in Sex and the City's season 4 episode "Defining Moments." He entered the gang as a new boyfriend of Miranda's. His lack of boundaries soon becomes an issue for the lawyer, especially his habit of keeping the bathroom door open.

19 of 25

Elizabeth Banks (Catherine)

Elizabeth Banks on 'Sex and the City'. HBO

The year before she played Lindsay in Wet Hot American Summer, Elizabeth Banks had a bit role as Catherine in season 3's "Politically Erect." She played the fiancée to a guest at a political fundraiser where Carrie's then-boyfriend Bill Kelley is raising money.

20 of 25

Alan Cumming (Oscar)

Sarah Jessica Parker and Alan Cumming on 'Sex and the City'. HBO

Alan Cumming graced SATC with his presence in the fourth season. Appearing in "The Real Me," he played Oscar, a fashion designer who is dressing Carrie for a runway show.

21 of 25

Bobby Cannavale (Adam Ball)

Bobby Cannavale on 'Sex and the City'. HBO

Though Bobby Cannavale's SATC character had the full name of Adam Ball, he is better known as the man with "funky spunk." He's dating Samantha, but the two run into problems in the bedroom, despite trips to a health food restaurant.

22 of 25

Chandra Wilson (Police Officer)

Chandra Wilson and Kim Cattrall on 'Sex and the City'. HBO

Years before she made her way to Grey Sloan Memorial Hospital, Chandra Wilson played an unnamed police officer in "Anchors Away" during SATC's fifth season. She confronts Samantha, who is illegally posting flyers, but leaves her be once Sam explains that she is spreading the word against the philandering Richard Wright (James Remar).

23 of 25

Jon Bon Jovi (Seth)

Sarah Jessica Parker and Jon Bon Jovi on 'Sex and the City'. HBO

Jon Bon Jovi took time out of his recording career to film "Games People Play," a season 2 episode of Sex and the City. He meets Carrie at a therapist's office and the two are drawn to each other in the worst ways, as Carrie realizes she chooses the wrong men and Seth admits, "I'm really f---ed up about women. After I sleep with them, I completely lose interest."

24 of 25

Andy Cohen (Shoe Salesman)

Andy Cohen and Sarah Jessica Parker on 'Sex and the City'. HBO

One of Sarah Jessica Parker's best friends, Andy Cohen appeared in the season 6 episode "Let There Be Light." He played an unnamed shoe salesman who helps Carrie out on a trip to a department store where Charlotte is going blindfolded in her first step to help the blind.

25 of 25

Carrie Preston (Madeline Dunn)

Cynthia Nixon and Carrie Preston on 'Sex and the City'. HBO

In the season 2 episode "The Chicken Dance," Carrie Preston appeared as interior designer Madeline Dunn. As she works on Miranda's apartment, she meets Miranda's friend Jeremy, going on to marry him just weeks later.

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