 The Outsider gives a very inside look at what it means to be a filmmaker. Jarecki follows legendary writer/director James Toback (The Gambler, Two Girls and a Guy, Bugsy) through the insane making of his recent thriller When Will I Be Loved starring Neve Campbell. The documentary chronicles all phases of Toback s wild filmmaking journey as he shoots his movie in 12 days without a script and battles to get it distributed. Candid interviews with Woody Allen, Robert Downey, Jr., Mike Tyson, Harvey Keitel, Norman Mailer, Brooke Shields, Barry Levinson and more reveal the complex life and work of this compulsive gambler and exceptional film talent.