Born on November 5, 1968, in Daly City, California, the son of actors who divorced when he was five years old. He was raised by his father, Pete Rockwell, in San Francisco while his mother, Penny Hess, stayed behind in New York (he spent his summer vacations with her). Rockwell had what The New York Times described in 1998 as a "footloose upbringing" and, at age 10, made his brief stage debut playing Humphrey Bogart in an East Village improve comedy sketch starring his mother.He attended School of the Arts High School (San Francisco) with Margaret Cho and dropped out before graduation. He later received his high school diploma after his parents enrolled him in an Outward Bound-style alternative high school called Urban Pioneers because, as Rockwell explained, "I just wanted to get stoned, flirt with girls, go to parties." The school, the actor said, "had a reputation as a place stoners went because it was easy to graduate", but the program ended up helping him regain an interest in performing. After appearing in an independent film during his senior year, he graduated and moved to New York to pursue an acting career.
Rockwell has never been married, and stated in a 2007 interview, "I definitely don't want to become a parent. It's not my bag."
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