Prior to starring in films such as Trash and Women in Revolt in the early '70s, Woodlawn ran away from her Miami home at 15 and hitchhiked to New York City. This story inspired the first verse of Lou Reed's 1972 hit "Walk on the Wild Side: "Holly came from Miami, F.L.A. Hitchhiked her way across the U.S.A. Plucked her eyebrows on the way. Shaved her legs and then he was a she. She says, 'Hey, babe, take a walk on the wild side."
Following her work with Warhol and Morrissey, Woodlawn failed to find mainstream success. She appeared in a handful of independent films in the '90s, including Billy's Big Hollywood Kiss and Night Owl, and recently appeared as Vivian on the first season of Transparent.