Bradley Cooper
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
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
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
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
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
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.
Sarah Michelle Gellar
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.
David Duchovny
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
Appeared in: season 4, episode 2
Klum played herself as she strutted down the runway alongside Carrie in an empowering fashion show.
Lucy Liu
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
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
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.
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