It's not that James Toback has never ventured into Hollywood. He wouldn't claim that he has all ill-will against the industry - he's got the script for Bugsy and Warren Beatty's friendship to speak to that - but he's got that "independent spirit" if you will. He's made some movies that, frankly, some of us just haven't seen or aren't available (Exposed and The Big Band come to mind). And in 2003 he got the opportunity to make any movie he wanted, as long as it was for two million, and came up with When Will I Be Loved, a quickly-baked romantic drama starring Neve Campbell. It was shot in eleven days, and it took a while to find a distributor. Toback is told at one point, "people still look for the new Quentin Tarantino." He ain't it.
The Outsider has the potential to look at Toback a little *too* favorably or with a little too much reverence to his pretensions. But thankfully the interviews and clips and Toback himself are quite candid about the man-myth-legend himself. He's a compulsive gambler and has never quit (although he has quit cigarettes cold turkey), and is described by Robert Downey Jr as "a genius and a retard", as someone who is quite brilliant but can be pushy on the sets of his movies. And yet one sees how dedicated Toback is to his craft, of exploring the themes in his movies (sexuality, obsession, madness, excess) and it's great to see him still working even if not all of his films are successes or if he gets it all out to audiences (Harvard Man, for example, was a true flop).
And entertaining are hearing the anecdotes and stories Toback has to tell, or those around him. There's a rapper, for example, who helped produce his film Black and White who talks at length about the use of the "N" word and how Toback actually *is* one to him, but in the friendly sense of the word (i.e. not "you white man" but "Hey, my N***a!). We also hear about his use of LSD, his friendship with Jim Brown, his idol Norman Mailer, and just see the rigorous and very on-the-fly process of When Will I Be Loved. It actually made me appreciate the film he made a little more (when I saw it I found heavy flaws among its virtues). For what it's worth, The Outsider shows Toback as an artist with something to say, even if his "brand" is not what Hollywood always, or rarely, wants. It's entertaining and informative.