Appeared in: season 3, episode 13 Gellar made a noticeable cameo when she played Carrie’s loud agent Debbie who tried to get her to sign a movie deal based on her life.
Bradley Cooper
2
Appeared in: season 2, episode 4 Cooper played Jake, Carrie Bradshaw’s love interest after a failed photo-shoot brought her self-esteem way down.
Justin Theroux
3
Appeared in: season 2, episode 15 Theroux perfectly embodied the awkward writer, Vaughn, who went out with Carrie several times. And all could’ve ended well if she hadn’t hit it off better with his mother than with him.
Elizabeth Banks
4
Appeared in: season 3, episode 2 In an if-you-blink-too-fast-you’ll-miss-it moment, Elizabeth played a helpful party guest who gave a distressed Charlotte some much-needed dating advice.
Vince Vaughn
5
Appeared in: season 3, episode 14 The charismatic Vaughn was lucky enough to be Carrie’s fun fling while in LA, but she quickly discovered he was actually a wolf in sheep’s clothing.
Kat Dennings
6
Appeared in: season 3, episode 15 Dennings portrayed a 13-year-old socialite who made Samantha run around New York trying to throw her a perfect birthday party.
Timothy Olyphant
7
Appeared in: season 1, episode 4 In season 1, Carrie was still torn between dating older men and having fun with twenty-something-year-old guys. Olyphant’s character helped her say goodbye to younger men once and for all.
David Duchovny
8
Appeared in: season 6, episode 10 Duchovny appeared as Carrie’s high school boyfriend she kept having second thoughts about. Their reunion brought back old feelings and new discoveries.
Heidi Klum
9
Appeared in: season 4, episode 2 Klum played herself as she strutted down the runway alongside Carrie in an empowering fashion show.
Lucy Liu
10
Appeared in: season 4, episode 11 Liu also made a cameo as an exaggerated version of herself who contemplated hiring Samantha as her main PR person.
Jennifer Coolidge
11
Appeared in: season 6, episode 3 Coolidge gave our 4 main ladies a hard time when she invited them to her party that turned out to be an excuse to sell her unusual purses.
Matthew McConaughey
12
Appeared in: season 3, episode 13 McConaughey had a lot of fun playing a version of himself who wanted to become Mr. Big in a movie adaptation of Carrie’s life.