For years, rerun-obsessed corners of the internet have been plagued by a persistent mystery: If the powers that be behind Sex and the City were aware that they'd cast Justin Theroux in two different guest-starring roles in back-to-back seasons—both writers, and both attempting romance Carrie Bradshaw throughout their designated episodes—and, if so, why they made this bold, reality-defying decision. Finally, more than two decades after his first cameo aired, Theroux himself has cleared up the conundrum.
In a new episode of PeopleTV's "Couch Surfing," Theroux revisited both of his SATC appearances. "Sex and the City was one of those shows that they burned through every actor in the first couple seasons, I guess. It's like Law & Order: It's kind of a rite of passage, you have to do Sex and the City," he said, though he noted that he's actually never guest-starred on an episode of Law & Order—perhaps exempted from this particular tradition because he doubled up on his SATC allotment.
Theroux went on to explain that when the showrunners approached him about doing a second episode, he readily agreed. "They said, 'Well, we have to figure out a way to make you look different.' So we were like, 'Let's just shave my head and have short hair,'" he recalled, joking, "So, that was me diving into the role."
To be fair, Theroux's SATC characters look about as different as one person can without undergoing a total physical overhaul. In the season one episode "The Monogamists," he played Jared, an up-and-coming author and acquaintance of Carrie's friend Stanford who wears ostentatious patterned clothing and stacks of shark-tooth necklaces, and says things like "groovy" and "ciao." His interaction with Carrie lasted less than a minute, in which he had time to brag about the "kickass review" his book had just received, suggest Carrie write about him for her next column, and smirk as Stanford revealed that Jared had just been named one of New York magazine's "30 Coolest People Under 30" in the city. Needless to say, Carrie did not end up attending the party he invited her to, and that was the end of Jared.
Only a few episodes later, in season two's "Shortcomings," Theroux has been transformed into Vaughn Wysel, a short-story writer who, like his predecessor, is being profiled in a major magazine, this time in a fashion spread for GQ. Though Vaughn is much more tolerable than Jared—he wears monochrome black outfits, nondescript wire-rimmed glasses, and, yes, that infamous buzz cut—Carrie still ends up calling things off before the episode's end, once she realizes that she likes Vaughn's family more than she likes him, and that they're unable to work through his problems in the bedroom. "I'm a premature ejaculator in this episode of Sex and the City and I'm clearly hung up about it—typecasting!" Theroux joked about his character on Couch Surfing, before hastily assuring viewers that that's not actually the case.
Revisit Theroux's double star turn on SATC in the videos below.