Outside of the Law & Order extended universe, no show’s casting decisions have the level of “hey, it’s that guy!” as those guest stars on Sex and the City. Just as nearly every established actor has popped up as a Law & Order criminal, nearly every struggling male actor in the ‘90s had a turn as a guy that held Carrie’s interest for five minutes — before she got bored and returned to her toxic relationship with a man who absolutely smelled like an old shoe filled with scotch.
Many men who momentarily held Carrie’s attention went on to have storied careers — something that sadly cannot be said of all of the series’ heroines. Sure, Miranda hooked up with Will Arnett and Jim Gaffigan, and a pre-fame Bobby Cannavale played Samantha’s “funky spunk” lover with an appropriate amount of shame in his eyes.
But Carrie regularly hung out with the stars of tomorrow: she made time with pee-loving-politician-turned-Roger-Sterling John Slattery and Dean “Dummy” Winters. She let Justified’s Timothy Olyphant make her toilet-paper coffee. And she dumped future Oscar-snubbed auteur Bradley Cooper on the curb, presumably due to his weird ratty Taylor Hanson wig.
However, only one actor has the distinction of losing Carrie’s interest twice. That honor goes to noted actor, screenwriter, abs-haver, and former Anistonian Justin Theroux. In Season 1 Episode 7, “The Monogamists,” Theroux plays Jared, a man at a bar wearing a hideous choker, who babbles about his novel and how hot Carrie is, presumably so no one brings up his choker (it might be two chokers? Either way, there are 100% some shark teeth hanging from it).