Filmed over an 8-month period, The Outsider follows James Toback through all phases of the making of his new film (shooting, editing, scoring, and release). The movie develops through frank conversations with him about his obsessions (gambling, drinking, drugs, and sexual exploration) and how they manifest themselves in his films by interweaving clips from all of his movies. The film also contains candid, revealing conversations about film and life with Toback's collaborators including: Woody Allen, Robert Downey, Jr., Mike Tyson, Harvey Keitel, Neve Campbell, Norman Mailer, Brooke Shields, Barry Levinson, Jim Brown, Robert Towne, Brett Ratner, Roger Ebert, Bridget Hall, Damon Dash, Woody Harrelson, Bijou Phillips, Jeff Berg, Dominic Chianese, and Power from Wu-Tang Clan.
| Directed by | Nicholas Jarecki |