With The Outsider, cinematic badboy James Toback gets in front of the camera for first-time filmmaker Nicholas Jarecki.

“Who is James Toback?” That’s the question documentary filmmaker Nicholas Jarecki poses in The Outsider, a freewheeling and highly watchable portrait of the director of idiosyncratic films like Fingers and Black and White.

Jarecki introduces his subject, the Oscar-nominated screenwriter of Bugsy, on the set of a 2004 film for which Toback had high hopes. When Will I Be Loved, which starred Neve Campbell as a young woman on the make, would, like many of Toback’s films, be a minor presence at the box office. But because the movie pivots on one of Toback’s pet subjects — sexual exploration — it serves as a handy launching point for an overview of the director’s interesting, if inconsistent, career.

If you’ve watched his movies, then to an extent you know Toback. His script for The Gambler, the 1974 film that starred James Caan as a gambling-addicted professor, famously grew out of Toback’s compulsive betting. The Pick-up Artist(1987) and Two Girls and a Guy (1997) are, on certain levels, replications of his checkered relationships with women. Harvard Man (2001) is a fictionalized version of his LSD-taking college days. And like almost all of his films since, Fingers is fascinated with sexual transgression and liberation.

Toback has always chosen to tell personal stories and accept the smaller audiences that come with them. There might not be a more proudly autobiographical filmmaker working today — a point Jarecki makes in dozens of interviews with people such as Robert Downey Jr., Barry Levinson, Woody Allen, Mike Tyson, Harvey Keitel, Roger Ebert, Brooke Shields, Robert Towne and Jim Brown, the football legend and longtime Toback friend.

The Outsider (Outsidermovie.com) opens Fri., June 16 at Cinema Village (Cinemavillage.com) in Manhattan.

Filmmaker: Nicholas, one of the techniques you use in the movie is to ask people, “Who is James Toback?” So let me ask you that.

Jarecki: James Toback is a fusion of two distinct personalities, one a refined, highly educated, highly intelligent aesthete, one a compulsive, neurotic gambling maniac who delights in taking huge risks. Both of these halves form an interesting filmmaker.

Toback: And I would say James Toback is in perpetual motion, usually in progress, sometimes in regress.

Filmmaker: Were you hesitant, James, to let him tail you and talk to your friends and make a film about you?

Toback: I had only one minor hesitancy. I felt from the interview we had done for his book [Breaking In: How 20 Film Directors Got Their Start] that his good intentions, seriousness and intelligence were not in question at all. My only question, not having seen anything he’d shot, was did he have any considerable cinematic skill? I can’t stand watching movies — unless it’s a stupid comedy, which I have a weakness for — that are made by people without any real cinematic finesse. And I thought to have one movie made about my work, which is all that is likely to happen in a lifetime, if that, it would be unfortunate if it were done clumsily. That I simply couldn’t know until he’d done it.

And then I was very, very pleased from the first, because Nick showed me a bit that he’d put together.

Jarecki: I’ll never forget that day. Jim watched it, and at a certain point I just saw this huge sigh of relief.

Toback: It ended up that it was going to be helpful for the movie to have a lot of people [from the film world] participate. By that time I was certainly sufficiently excited about the film that I felt no hesitation in telling people who called me to go ahead and do whatever they wanted and say whatever they wanted to say. Some were a little reluctant to do it. Harvey Keitel really only wanted to do it if I were going to be there…. There’s a thing that [Jarecki] captures with Harvey; with Downey; with Brooke; even though it’s quite brief, with Bijou Phillips; with Roger Ebert; with Tyson; with Jim Brown. These are very impressive portraits of these people.

Filmmaker: James, your personal history — with drugs and women and gambling — has become the stuff of most of your movies. Which is why Woody Allen, when speaking to Nick, described you as one of our most personal filmmakers. Can you imagine being any other way?

Toback: No, I can’t imagine my being any other way even if I wanted to be another kind of director, because I wouldn’t be any good at it. I was talking throughout the making of X-Men: The Last Stand to [the film’s director] Brett Ratner. Brett’s a good friend of mine. I was, let’s say, aware of how he was being observed and communicated to [by 20th Century Fox] during the making of that movie. I couldn’t do that.

It’s great to have $200-and-something million to make a movie, but my idea of money in relationship to a movie is to receive it, make the movie while spending it and then show it to the person who financed it — not to be talking to the person. I have a total openness with everybody who’s actually working on the movie and a total shutout of anyone who’s not working on the movie with me. The idea of allowing the nervous dread of outsiders with a stake in the movie to intrude on your consciousness while shooting a movie is inconceivable to me. And I think the price that you pay, which is making a movie for infinitely less money, is worth it. It is for me. It’s a limitation. But I thrive on this.

Filmmaker: Film historian David Thomson, in The New Biographical Dictionary of Film, says your first movie, Fingers, is your best. I wonder if you agree, and also if you look at your career in this way, ranking some movies ahead of others.

Toback: I think that my best movies — and I wouldn’t put one above the other, necessarily — are Black and White, Two Girls and a Guy, Fingers, When Will I Be Loved and Harvard Man.

Filmmaker: Do you agree with Jim’s hierarchy?

Jarecki: I would expand to say the two films that Toback left out were The Gambler and Bugsy. And actually the way I became interested in Toback was through The Gambler, which I regard as the greatest movie on gambling in cinematic history. From my perspective, Bugsy is also one of the best Hollywood scripts in a long time. I am not sure that I want Toback to have directed Bugsy because I like it how it is. It would be a different movie. I’d like to see that movie also, but I wouldn’t want to erase the one that exists in order to get it. Because I think the one that exists is an interesting fusion of his sensibility with two other people’s, Warren Beatty’s and Barry Levinson’s.

Filmmaker: I read in Salon and maybe you still do this, that you approach 50 people a week, by your estimate — 40 of whom are female — and ask them if they’d ever thought about acting. Is that true?

Toback: It might be a bit of an exaggeration, but I’ve always felt that casting should be an informal, impulsive intuitive process and not a formal one that involves choosing people from a preordained pool of actors. If you’re talking about the stage, yes, training is needed, study is needed, craft is needed. Film, in its nature — not the way I make film, the way film is — is so broken up into pieces, is so fragmented, that to give a quote-unquote “performance” is a practical impossibility. You cannot give a performance because what you are doing is not performing. What you are doing, over a period of days, weeks or months, is providing a director with an infinite number of options, which, if he’s as good as he should be, he will be able to take and fashion a performance from.

By that logic you want to use people who stimulate you and excite you and intrigue you in ways that have nothing to do necessarily with a performance they gave somewhere else. Something about them: a look, a smile, a way of walking. Some of the best people I’ve used I’ve met in utterly random situations…. I met Carole Francis on the street, the girl who was with Jim Brown and Harvey Keitel in Fingers. There are a hundred beautiful, pretty blonde girls you can see week after week on the street. There was something about her right away that I knew would just fit and work. Tisa Farrow (who was also in Fingers), she’d acted a little bit, but I didn’t meet her as an actress. I basically picked her up. I just thought that she had something in her eyes that was kind of haunting.

I think the idea of acting as a profession in relation to movies is suspect. It is something that you can’t really do for more than bits and pieces. And a lot of well-trained stage actors hate to hear that. But they’re also very frustrated by film acting, most of them, because of that. You can’t say acting is acting. I think stage acting has much more to do with performing on the stage — whether it’s singing, stand-up comedy, other forms of live, continuous performance — than with film acting, which is another activity entirely, and which is suited to all kinds of people who have not had the training.

Filmmaker: One of your producers uses the word “impossible” when talking about marketing his movies.

Toback: I disagree with that. He says that in the movie. I think that it is difficult to market them, and the marketing mentality in Hollywood really recoils at difficulty. They want movies that are going to market themselves. But the fact is, there is a way of marketing good movies. Because most movies are bad, and by the time that people catch up with them they resent having been hustled. So if you actually deliver a movie that an audience will respond to, you should be able to find a way. Obviously some are much easier than others.

Filmmaker: Nick, how did you get Woody Allen to talk on the set of Melinda and Melinda?

Jarecki: A great stroke of luck. It turned out that Brian Hamill, who was Toback’s still photographer and good friend, also happens to be Woody’s still photographer and good friend. I thought it was critical to get Woody, because he’s so similar to Toback. Obviously their films are completely different, but they’re both New York filmmakers who tell personal stories and have had long careers and are controversial personalities. So I said to Brian, “What do you think about broaching the subject with Woody?” He literally called me back an hour later and said, “Woody said be here tomorrow morning.” He has such an interesting perspective, as does Jim, on independent filmmaking. What he said about Jim’s films is that they’re not factory-made.

Filmmaker: Robert Downey Jr., in the movie, and David Thomson, in his book, both note that when you were younger, Jim, you thought you wouldn’t make it to middle age.

Toback: Nor did I have any desire to. I used to think that I was going to be dead at 26 — that was the age.

Filmmaker: And now you’re 61. Surprised?

Toback: I might as well be 133. Sixty-one is so absurd to me that I’m embarrassed to say I’m 61. Not embarrassed because it’s too old, embarrassed because it’s not even in the zone of possibility. I remember as if it were yesterday my father’s 50th birthday. At 50 he looked like a handsome 35-year-old guy. I remember thinking, How can I have a father so old? It was just mind-boggling that I was connected to somebody who was 50 years old. And I’m 11 years older than that. It’s ridiculous. But now that I am 61 it’s not actually as bad as I thought it would be. I’d rather be alive than dead — let’s put it that way.

Filmmaker: What’s next for both of you guys?

Jarecki: I’m doing a fictional film called The Informers, which I wrote with Bret Easton Ellis, based on his best-selling book of the same name. It takes place in L.A. in the ’80s. It’s a multi-plot story like Boogie Nights, Short Cuts, about a studio executive, a cocaine dealer, a mistress, a rock star, a vampire and a kidnapper.

Toback: If you have a loaded pistol, I will put it to my head and force myself to decide which of the three movies I’ve been toying with that I’m finally going to move ahead with. But short of that, I may delay a little longer before deciding.