In 1999, Nicholas Jarecki graduated from NYU with a film degree, but no idea how to get a job making films. He rather ingeniously solved that dilemma by asking 20 established filmmakers, from John Schlesinger to Neil LaBute, to tell him how they got started in the business. "It was my mom's idea," Jarecki says over lunch at a midtown steakhouse. "I was complaining about how I couldn't get a job, and I told her that I just needed to get a bunch of directors in a room and ask them how they did it. And she said, "That would make a great book."

Published in 2001, Breaking In: How 20 Film Directors Got Their Start, described just that, and it bought Jarecki the opportunity he'd need to make his own directorial debut. One of the directors Jarecki interviewed was James Toback. The auteur behind such notoriously love-it/hate-it fare as Fingers, The Pick-up Artist and Two Girls and a Guy, the stories Toback told during his sessions with Jarecki were full of sex and drugs and crime and just a little bit of Dostoyevsky; maybe unsurprisingly he stood out to Jarecki as "having had the most interesting life" of anyone he’d interviewed. When the younger director heard a few years later that Toback was getting ready to shoot an erotic thriller in New York City, Jarecki left message after message for Toback, begging to be allowed access to the set. No response. Just about to give up, Jarecki placed one more call. It was the day before shooting was to start. Toback answered.  “He said, “Get your camera and come down tomorrow,” Jarecki recalls. “So I did.” The Outsider, which premiered at this year's Tribeca Film Festival, was thus born.

Toback had been given $2 million by foreign investors, on the condition that he complete a film in 21 days. That film, When Will I be Loved?, starred Neve Campbell as a sexually voracious trust-fundette who turns various tables on the creepazoid men her life who underestimate her. It opened in 2004 to disastrous box office and predictably mixed reviews, but made more than double its money back on home video -- proving the old adage that when it comes to home entertainment, a naked Neve Campbell never hurts.

Jarecki tracked the production from that first day (“Jim was literally writing the script on the way to the set with me in the car,” he says) to the film’s release. The Outsider, the result of that sanctioned stalking, comes off as something like a love letter – but when your subject is, to borrow a line Norman Mailer uses in the film, "half genius and half all fucked-up", the pledging of such love is a fairly fascinating pursuit.

In circles of everyday, cookie-cutter urban cineastes, pledging love for Jim Toback is not a popular thing to do. When I tell Jarecki that my own academic interest in Toback was scoffed at in film school, he’s quick to jump to the other filmmaker’s defense. “That’s just insane,” he says, shaking his head. "I think it's juvenile not to regard Jim's work as worthy of study and debate. He's one of the rare filmmakers addressing adult themes and issues in today's cinema, gray areas, questions of morality, the valence of 'right'.  As a filmmaker he functions in the theater of ideas. That's so obviously worth a serious look. I think it's just knee-jerk prudishness to dismiss his films outright. Have the people dismissing them even ever watched them?"

“Insane”, perhaps, but Toback’s trouble with the critical establishment is well documented. Most recently he exchanged barbs with Entertainment Weekly’s Lisa Schwarztbaum, who called When Will I be Loved? “a muddled bitch-in-heat fantasy” (Roger Ebert, on the other hand, called it a masterpiece). It doesn’t surprise me that the man who drops dirty bombs like Black and White would inspire strong reactions. Of course some professional critics would take great joy in puncturing the bloated aspects of Toback’s ventures – with a filmmaker so willing to present himself on a platter, there are just so many pithy possibilities for the teardown. What ends up being most surprising about The Outsider is not just that it obstinately avoids the practice of such criticism, but that it has very little concern for Toback’s detractors one way or another.

Spend a little time with Jarecki and flashes of Tobackian wit pop out every now and then. When our waiter drops the check with the words, “It’s been a pleasure,” Jarecki cocks his head and says, “Really, Steve? Has it been “a pleasure”? I reserve the word “pleasure” for things like sex, chocolate, crack cocaine.” It doesn’t come as a shock to hear that Jarecki responds to Toback on a personal level. “I do, I really like the guy,” Jarecki says. “Jim and I definitely became friends.” That friendship steers The Outsider into very insider territory, and though the critical distance precluded is occasionally missed, there’s certainly something to be said for the access and intimacy the friendship helps Jarecki obtain. Most of the interviews have a clubby, friends-sitting-around bullshitting feel that is sorely missing from most celebrity documentaries. Toback’s friends trust Jarecki because they know Jim trusts him.

Once allowed into the inner circle, Jarecki exposes Toback’s uncanny ability to draw in fellow half-genius/fuck-ups.  From Bijou Phillips to Mike Tyson, from Brooke Shields to various members of the Wu-Tang Clan, Toback has patched together some kind of ad hoc family of outsiders, out of which the only immediately discernible common denominator is the level of devotion each member beams towards the auteur. Some of these de facto siblings make it clear that they’ve chosen to be there – when Neve Campbell, for example, explains that she simply “wasn’t happy” making bad movies just to pay for a lifestyle, you actually believe her – but what’s really interesting are the actors who have found a home working for Jim after having fallen from some kind of mainstream sphere of success.

In many cases, this devotion is so unfettered that it almost critiques itself. “He’s one of the greatest directors of all time. Everyone knows that,” declares bad-girl former model Phillips, her tone of voice somewhere between a squawk and a coo. In another scene, Brooke Shields gazes up at Toback as he praises her performance in Black and White. Jarecki’s camera pulls in on the actress, as her face begins to disfigure with humility. As she fights back tears, one almost gets the sense that, to the right actress, praise from James Toback is akin to a kiss from some kind of God.

None of this would work without counterpoint, and the profiterole of praise whipped up by a handful of actresses gets its puncture in the form of testimony from one of Toback’s most frequent collaborators. “[Jim’s] a genius and he’s a retard,” says Robert Downey, Jr, in a fierce, rapid-fire, intensely felt monologue. I mention to Jarecki that Downey seems to be the interviewee with the widest range of emotions towards Jim. “I think that’s absolutely correct,” he says. “Downey and Toback are kindred spirits. They share a bond of madness; they've both been through the fire in their own ways. It's that special bond that lets them do such intriguing, visceral work together."

Working on a film clearly does something to Toback. He gets caught up in the mad rush of it all, he feeds on the mutual appreciation swirling around both cast and crew, he gets high on making it up as he goes along.  By the time When Will I Be Loved? is finished, Toback seems almost invincible. After the film wraps, Jarecki captures Jim striding down a Manhattan street, announcing to a cell phone that he is “either totally insane, or" this film is the best work he’s ever done.

Cut to distribution hell – meeting after useless meeting, phone call after dissillusionary phone call, and soon that either/or statement of sanity comes back to haunt Toback. Distributors don’t want to get into to business with him; his films are notoriously hard to market and, theatrically speaking, haven’t historically done well. Loved eventually gets picked up by IFC Films, but it’s not a process exited from without a good deal of frustration. “I know probably 1000 people,”  Toback says, livid over being told that the audience for his work is too small. “They would respond to this film.”

That, in the end, may be the problem: James Toback makes films for the 1000 people he knows, but he’s caught up in a racket that counts its customers in considerably higher digits. Sometimes these films are very good and deserve to be seen by a much wider audience, but he’s not going to compromise in any way in order to make his work (or, for that matter, his life) commercially palatable in any way. The Outsider ends up being a portrait of an artist making art-for-arts-sake from within one of the biggest import/export industries in the world. Unlike virtually any other celebrity profile, it’s tinged with the unavoidable yet bittersweet notion that going one’s own way might be the hardest way of all, and at the same time, is still absolutely the only option.