Sex and the City was a groundbreaking show when it debuted two decades ago, and helped launch the careers of many actors — or reinvigorate those of others.
Most of the notable cameos came in the form of men Carrie Bradshaw (Sarah Jessica Parker) was dating. In celebration of the show’s 20th anniversary, here are a dozen famous faces that played Carrie’s love (or sometimes just sex) interests on Sex and the City.
Bradley Cooper
Appearance: “They Shoot Single People, Don’t They”
Before he was a leading man, Cooper made his television debut as one of Carrie’s makeout buddies, until he thrust an unflattering magazine cover of herself in her face. He directs and stars opposite Lady Gaga in the upcoming remake of A Star Is Born.
Timothy Olyphant
Appearance: “Valley of the Twenty-Something Guys”
Very early on in the series, Olyphant played a 20-something who hooked up with Carrie after a party. At first, she was attracted to his carefree attitude and lack of responsibility, but not his dirty apartment he shared with a roommate. Olyphant would later play the lead in Justified and The Santa Clarita Diet.
Jon Bon Jovi
Appearance: Games People Play
The legendary rocker appeared in Season 2. Carrie meets him in her therapist’s waiting room, and eventually dates and beds him. Unfortunately, she learns that he loses all interest in a woman after sleeping with her, which is why he’s seeking therapy.
Ron Livingston
First Appearance: “Hop, Skip and a Week”
Most fans know Livingston from the cult classic Office Space, but he played Carrie’s boyfriend Jack Berger for an extended arc in Seasons 5 and 6. As a fellow writer, he was her intellectual equal, but the two lacked the chemistry or “zsa zsa zsu.” They would find it eventually, but Berger became jealous of Carrie’s success and broke up with her … on a Post-It.
Justin Theroux
First Appearance: “The Monogamists”
Producers loved Justin Theroux so much that he appeared as two different characters. He first appeared as Jared, who flirts with Carrie in a bar. He appears a season later as Vaughn, who suffers performance issues in the bedroom. She dumps him after she realizes she loves his family more than she loves him. Theroux went on to star in Six Feet Under and The Leftovers.
David Duchovny
Appearance: “Boy, Interrupted”
Duchovny played Carrie’s handsome high school sweetheart. They immediately rekindled their spark, until Carrie learned he had admitted himself into a mental instutition. Duchovny would go on to star in Californication and reprise his career-making role in The X-Files.
Vince Vaughn
Appearance: “Sex and Another City”
The episodes where Carrie visits California are filled with celebrity cameos, with Matthew McConaughey, the late Hugh Hefner, and the late Carrie Fisher playing themselves. Vaughn played Fisher’s assistant Keith, who tried to pass himself off as a producer and her mansion off as his own. Fisher returns early and kicks both of them out.
John Slattery
First appearance: “Where There’s Smoke”
Before playing an ad exec on Mad Men, Slattery played an aspiring local politician on Sex and the City. He was handsome and confident, two qualities Carrie found appealing. Unfortunately, he had a watersports fetish, and her attraction dried up.
John Corbett
First appearance: “No Ifs, Ands, or Butts”
A furniture designer with a heart of gold, many thought Aidan was “the one” for Carrie. Unfortunately, her fear of commitment led to a broken engagement and eventual complete split. Corbett’s character has been a fan favorite for years; which did you prefer — long-haired Aidan or short-haired Aidan?
Mikhail Baryshnikov
First appearance: “One”
Legendary ballet dancer Baryshnikov was an unusual choice for Carrie’s lover: older, old-school, foreign. His character — Aleksandr Petrovksy — was so charming he even convinced her to leave New York for Paris. Carrie would learn that his passion for work exceeded his passion for her, and all his romantic gestures were simply too much to handle.
Chris Noth
First appearance: “Sex and the City”
Noth played “Mr. Big,” Carrie’s on-again/off-again boyfriend throughout the entire series. Introduced in the pilot, he had more appearances than any other guest star — 41 episodes in total. In the finale, he dashes off to Paris to rescue an unhappy Carrie from Petrovsky. In the first feature film, they are married. In the sequel, her fidelity is tested when she runs into Aidan.
Who was your favorite Carrie Bradshaw boyfriend?
