Named for auteur d’excés James Toback, whose career since Fingers has been one big guilty pleasure, Nicholas Jarecki’s The Outsider is among the great docs about moviemaking; you’d compare it to Hearts of Darkness and Burden of Dreams if only Toback, a notorious gambler, had won the chips to indulge himself as thoroughly on location as his addictive personality would prefer. Here the indie hustler’s equivalent of directorial jungle madness is taking $2 million from British bankers on condition of starting to shoot a script, any script, in less than a month; a few short days into the two-week (!) production of When Will I Be Loved, Toback’s New Wave–in–New York ditty with Neve Campbell as a penthouse-lounging femme fatale, the filmmaker has eight uncast roles and a shitload of dialogue left to write. Pontificating off the cuff, Toback could be describing his own narcissist’s m.o. when, with characteristic modesty, he calls Loved an “exploration of sexual and psychological and philosophical capacity”—this before giving blow-by-blow direction to Frederick Weller and three nubile blondes for an endearingly gratuitous ménage à quatre scene in sunny Central Park.
Jarecki is allowed ample access to the crazy shoot, but he’s much less interested in the minutiae of guerrilla production than in the psychology of an obsessive artist and the genuine, infectious love it inspires in his collaborators. “I felt like Shakespeare didn’t die,” gushes Robert Downey Jr. of reading Toback’s The Pick-up Artist—in which, Downey adds, “I was essentially playing him.” Toback’s eclectic casting naturally extends to the doc, whose often hilarious talking heads include Brooke Shields, Norman Mailer, Brett Ratner, Bijou Phillips, and Mike Tyson—none of them as big a character as Toback, the sensitive pussy-hound with a bear-like physique, the player who wears both balls plus his heart on his sleeve. The doc’s climax—the outsider wandering midtown in search of distribution, Chicago’s “If You Leave Me Now” wailing on the soundtrack—is a tiny masterpiece of perverse pathos, as oddly moving as anything in Two Girls and a Guy.