An author, poet, comedian, and radical performance artist, he is best known for works such as The Wedding of Everything (1983) and Pain Journal (1996). He also appeared in several music videos, including Nine Inch Nails' controversial piece, Happiness in Slavery.
He attended California State University, Long Beach and the University of California, Irvine. Early in his career, he joined The Groundlings, a Los Angeles-based improvisational theatre troupe.
He was the focus of the documentary, SICK: The Life & Death of Bob Flanagan, Supermasochist. He died of cystic fibrosis at the young age of forty-three.
He was born in New York City, and he grew up in Southern California. He was briefly married to Sheree Rose.
He was in the film, The New Age, with Peter Weller.