25 of Sex and the City's most famous guest stars

Nathan Lane had a memorable appearance in a 2002 episode of Sex and the City. Starring in season 5's "I Love a Charade," Lane played Bobby Fine, a lounge singer who has been friends with Carrie Bradshaw (Sarah Jessica Parker) 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.

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.

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 the photographer shooting nude pictures for Samantha Jones (Kim Cattrall).

Comedic actress 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 in 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.

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. He 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, who was played by Valerie Harper.

Following his turn as Mulder in 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.

Vince Vaughn played Keith Travers in "Sex and Another City," a season 3 episode in which the ladies travel to Los Angeles. While he 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.

At the height of her Charlie's Angels fame, Lucy Liu played herself in a season 4 episode entitled "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.

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.

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?'"

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.

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.

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 guy 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."

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.

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.

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 (Cynthia Nixon), but his exhibitionist tendencies become a problem.

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

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 became an issue for the lawyer, especially his habit of keeping the bathroom door open.

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 was raising money.

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.

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 ran into problems in the bedroom, despite trips to a health food restaurant.

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, as Sam is illegally posting flyers, but leaves her be once Sam explains that she is spreading the word against the philandering Richard Wright (James Remar).

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."

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.

In Sex and the City's second season, Carrie Preston appeared as interior designer Madeline Dunn. As she worked on Miranda's apartment, she met Miranda's friend Jeremy, going on to marry him just weeks later.