The ladies of Sex and the City dated a lot—I mean, that was kind of the point of the show, right? There were a few serious boyfriends and eventually, husbands, but the friends also went on lots of terrible flings and dates in between.
Since the show debuted fifteen years (today!), some of the guest stars who played those horrible guys have now gone on to A-lister status. It's so fun catching them in reruns, often with bad hair! Check out the list here.
Who was your favorite boyfriend on Sex and the City? Were you surprised about anyone on this list? What's your favorite episode? Tell us in the comments below or tweet us @OKMagazine.
1. John Slattery
The 'Mad Men' star memorably played a politician who requested a sex act too dirty for even that group of ladies to accept.
2. Andy Cohen
Look fast! Andy played a shoe salesman helping Carrie try on a pair.
3. Bobby Cannavale
Before he was on 'Boardwalk Empire,' he was the "funky spunk" guy. That's all we have to say about that.
4. Vince Vaughn
When the gals took a trip to LA, Carrie was romanced by Vince's character, who pretended to be a big Hollywood agent but was actually a celebrity dog-walker.
5. Ron Livingston
Ron played a proper boyfriend on the show, and he was pretty great at it—until his character broke up with Carrie on a post-it. Ouch.
6. Craig Bierko
He was Carrie's adorable rebound in season four, but you may know him now as a lauded Broadway actor.
7. Daniel Sunjata
You may have seen him on 'Law and Order: SVU' or 'Grey's Anatomy,' but he played a cute sailor who romanced Carrie during Fleet Week.
8. Justin Theroux
Jennifer Aniston's fiance is so hot, 'Sex and the City' had to have him twice. He played a cute guy at a bar, then an actual boyfriend for Carrie for one episode.
9. Bradley Cooper
The future Oscar nominee played a hot almost-love interest for Carrie. His hair was long and bleached blonde at the time!
10. Timothy Olyphant
Right around the time he was playing a vicious murderer in 'Scream 2' (spoiler alert?), he also had a hardcore make-out session with Sarah Jessica Parker for the show.
11. Michael Showalter
The comedian popped up as a friend of Carrie's ex-boyfriend, who got an earful after the guy dumped her.
12. Will Arnett
The 'Arrested Development' star was actually serious for once, as a guy who would only have sex outdoors.
13. Mark Feuerstein
Miranda rocked his character's world when she suggested to him that all women fake it in bed.
14. Jon Bon Jovi
You knew the show was getting big when they booked guest stars like this one! Who could forget his sexy game of Twister with Carrie?
15. Matthew McConaughey
He would later romance Sarah Jessica Parker in 'Failure to Launch,' but on the show he is one of the few who didn't date a main character. He was just interested in making Carrie's columns into a movie!
16. David Duchovny
The 'Californication' star appeared as Carrie's high school sweetheart... who's now in mental institution.