Filmmaker Nicholas Jarecki offers a celluloid portrait of a cinematic mastermind at work in this documentary shot over an eight month period and following director James Toback through each phase of production of his 2004 thriller When Will I be Loved. From pre-production to final cut, Jarecki follows the existential-minded director through the entire process of making a movie as Toback opens up to the camera to discuss a variety of deeply personal matters and explore just how they have manifested themselves in such films as Love and Money, The Big Bang, and Black and White. Candid interviews with such well-known Toback collaborators as Woody Allen, Robert Towne, Harvey Keitel, Roger Ebert, Brett Ratner, show just how much impact the well-respected filmmaker has had in Hollywood despite his stubborn refusal to fit into the commercialized mold so frequently associated with the showbiz mecca.