After boarding school in Williamstown, Massachusetts, and Bennington College, where he majored in drama and visual arts, Theroux moved to New York and found work bartending and painting lofts. He was discovered in a 1994 Off Broadway show playing the lover of Beatles manager Brian Epstein and made his film debut in the 1996 indie I Shot Andy Warhol. After a cameo in Zoolander, Theroux gained a mentor in Ben Stiller. “He was the first person to read half-started screenplays I was writing as a hobby,” Theroux says. They collaborated on the 2008 comedy Tropic Thunder, which co-starred Robert Downey Jr., who recommended Theroux to write the Iron Man 2 screenplay. If the stars align, Theroux says, he’ll direct Zoolander 2 from his own script.
“Writing provides great cover, so I can do the acting jobs I want,” says Theroux, popping a fresh piece of Nicorette gum—Hollywood dessert—into his mouth. “It’s harder and takes so freaking long, but to me it’s more satisfying. As a writer you’re the architect; as a director you design the interior; as an actor you are nothing but the leg of a table.”