The 'Mad Men' star memorably played a politician who requested a sex act too dirty for even that group of ladies to accept.
Look fast! Andy played a shoe salesman helping Carrie try on a pair.
Before he was on 'Boardwalk Empire,' he was the "funky spunk" guy. That's all we have to say about that.
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.
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.
He was Carrie's adorable rebound in season four, but you may know him now as a lauded Broadway actor.
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.
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.
The future Oscar nominee played a hot almost-love interest for Carrie. His hair was long and bleached blonde at the time!
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.
The comedian popped up as a friend of Carrie's ex-boyfriend, who got an earful after the guy dumped her.
The 'Arrested Development' star was actually serious for once, as a guy who would only have sex outdoors.
Miranda rocked his character's world when she suggested to him that all women fake it in bed.
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?
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!
The 'Californication' star appeared as Carrie's high school sweetheart... who's now in mental institution.
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.