When you watch the iconic TV show Sex and the City, you tend to gloss over some of the random men in the love lives of Carrie, Samantha, Charlotte, and Miranda. But a re-watching of this sexy classic tells us how far some of these actors have come! For more an actors who took on bit roles before making it big, click here.
#1 Bradley Cooper as Jake (Season 2)
Cooper plays Jake, a guy Carrie picks up at a bar when she was down in the dumps by her less than flattering New York magazine cover. Carrie promptly leaves him before they hook up, when she sees him holding the said magazine.
#2 Mark Feuerstein as Josh (Season 2)
Miranda dated Josh, played by Feuerstein and admitted to faking orgasms with him. Even after so many tries, she had to fake it one last time right before she ended it. Afterwards, Feuerstein starred in his own show, Royal Pains.
#3 Alan Cumming as Oscar (Season 4)
We must say, Cumming is quite more memorable for us, given his flamboyant character, Oscar, in the show. When Carrie is asked to be a “model” in a charity fashion show, Oscar first dressed her in a floral gown then switching her outfit later on to jeweled underwear. That wasn’t the only thing to worry Carrie, as she fell on the runway and became “fashion roadkill” when Heidi Klum had to step over her.
#4 Eddie Cahill as Sean (Season 3)
Cahill is a younger guy whom Carrie dates and reveals he’s bisexual. He later on became Rachel Green’s assistant on Friends, named Tag Jones.
#5 Clark Gregg as Harris Bragen (Season 3)
Gregg played a guy pretending to be a surgeon who was really working at the Foot Locker, whilst Miranda was pretending to be a stewardess. Nowadays, he is more known as Phil Coulson in Iron Man, Iron Man 2, Thor, The Avengers, and Marvel’s Agents of S.H.I.E.L.D.
#6 Justin Theroux as Jarod (Season 1) and Vaughn Wysel (Season 2)
In season 1, Theroux played one of New York magazine’s “30 Coolest People Under 30,” smarmy, but unforgettable—which explains why in Season 2 we remember him better as the memorable Vaughn Wysel. Wysel suffered from premature ejaculation, but Carrie really wanted to stay with him in spite of that because she fell in love with his super liberal Upper West Side mother and family.
#7 Gabriel Macht as Barclay (Season 1)
Since he appeared in the first episode of the first season, forgive us for not noticing the current leading man on Suits. Macht played the artist friend of Carrie, Barclay, who records his sex with models.
#8 John Slattery as Bill Kelley (Season 3)
Slattery plays an aspiring Manhattan City treasurer who dates Carrie and has a sex fetish. He wants her to pee on him. Now, Slattery is more known as part of the cast of Mad Men.
#9 Will Arnett as Jack (Season 2)
Will Arnett played a guy Miranda meets at a bookstore and likes having sex in public places. As it turns out, it has more to do with the fact that he lives with his mom rather than being kinky.
#10 Vince Vaughn as Keith Travers (Season 3)
While in Los Angeles, Carrie meets Keith Travers, touting himself as the agent of Matt Damon. As she goes to bed with him, she find out he’s just a house sitter for Carrie Fisher.
#11 Jim Gaffigan as Doug (Season 4)
Playing a cartoonist for the New Yorker that dated Miranda, Doug was eventually dumped for his tendency to go to the bathroom without closing the door (Even during no. 2! Yikes.).
#12 Craig Bierko as Ray King (Season 4)
Jazz player Ray, played by Bierko, dated Carrie for a while, especially since he gave her the most intense orgasms ever. At the end of it all, she broke up with him because of his ADD. Currently, Bierko is a well known Broadway star.
#13 Glenn Fleshler as Shmuel (Season 1)
Charlotte dated Shmuel, played by Fleshler, a Hadistic artist. Fleshler later played Errol Childress in the HBO TV show, True Detective.
#14 Dean Winters as John McFadden (Season 2)
Winters plays John McFadden, Carrie’s f*ck buddy who she tries to think she can possible have a relationship with. He’s now more known as the no-good pathetic ex of Liz Lemon on 30 Rock. Check out these times when Liz Lemon taught us a thing or two about life.
#15 Timothy Olyphant as Sam (Season 1)
Olyphant played Sam, a 20-something guy Carrie has fun with. Now, Olyphant stars in the FX show, Justified.