He graduated from Terra Nova High School in San Francisco in 1982. Early in his career, he was a writer and cast member on Saturday Night Live.
He played the title character in the 1999 film Deuce Bigalow: Male Gigolo and its 2005 sequel Deuce Bigalow: European Gigolo.
He was married to London King from 1988 to 1990, and in 2011, he married Patricia Azarcoya. He and London had a daughter named Elle, who became a singer. He had another daughter named Miranda with Patricia.