Adrian Grenier made a name for himself as the likeably vapid mimbo Vincent Chase on HBO's Entourage.

Conceived on a commune in New Mexico, Grenier moved to Brooklyn with his mom as a baby and attended the LaGuardia High School of Music and Art and Bard College. Grenier earned his first acting work in indie flicks like 1997's Arresting Gena and 1998's The Adventures of Sebastian Cole, in which he played the son of a transsexual father. A year later, he hit the mainstream as the boy next door in the teen magnum opus Drive Me Crazy. He continued to appear in supporting roles in studio films—including Hart's War and AI—before landing his breakout role as Queens-boy-turned-superstar Vincent Chase on HBO's Entourage in 2004, leading him to parts in films like The Devil Wears Prada.

Yet like many a moderately successful actor before him, Grenier has parlayed his success in front of the camera into directing gigs, which, he says, don't require you to "go to the gym as much." He shot his first film before he earned his HBO fame, directing and producing A Shot in the Dark, a documentary about his search for his estranged father, John Dunbar. Grenier also made a short film, a black comedy called Euthanasia, and subsequently a doc that relied on his famous friends as subjects Teenage Paparazzo. If his budding filmmaking skills aren't enough, Grenier plays the club scene as the drummer in his band The Honey Brothers, who, according to the Village Voice, are "masters of Hawaiian-Applachian glam rock."—the cherry on top of the cliche sundae.

Grenier dated Melissa Joan Hart while the two were making Drive Me Crazy in 1999, and was recently linked to Kirsten Dunst, Sports Illustrated swimsuit model Melissa Keller, and pro-surfer Hannah Cornett. [Image via Getty]