'Shadowman': How to Turn a Nearly Impossible Subject Into a Compelling Feature

When the Tribeca Film Festival was founded 16 years ago, it was intended to help celebrate New York City and revitalize lower Manhattan in the aftermath of the 9/11 attacks. As such, the festival always features some hometown tales—movies for New Yorkers and the people who love them. This year, Shadowman is one of those films. The documentary revels in the mystique of the gritty downtown early ‘80s art scene, the birthplace of now-legendary names Basquiat and Haring, and also of their contemporary Richard Hambleton, the "Shadowman" to whom the film’s title refers.

Filmmaker Oren Jacoby was born and raised in New York and lived in the Lower East Side when he was starting his film career. Describing the neighborhood during that period, Jacoby recalls, "You'd wander blocks and blocks and blocks and not see a soul," but you would regularly see Hambleton’s expressive street paintings on the walls. 

"You just have to keep going. You just have to be persistent. You have to let nothing get in the way."

"I was a young filmmaker trying to figure out how to make a film about New York and about how you interact with the landscape," says Jacoby. "It never occurred to me that those images were a way in to tell a story." More than 30 years later, he was invited to an art opening in that same neighborhood—now expensive and elite—and he recognized Hambleton’s signature brushstroke.

“Suddenly,” he recounts, “I saw there's the story here of the relationship of the art in the city. That's something that Richard understood instinctively at the very beginning of his career.” Thus, the filming of Shadowman began, ultimately resulting in a complex feature documentary about a self-destructive artist who keeps creating at all costs. 

No Film School spoke with Jacoby before the film’s world premiere at Tribeca 2017 about how to handle a subject who ranges from apathetic to difficult to impossible—and see your project through successfully, nonetheless.

No Film School: Where you think that street art and documentary work overlap?

Oren Jacoby: Street art recognizes that the street is the place for art because it catches us unaware. We're exposed to something and we have an immediate visceral reaction to it. If it's good, it engages us. That was the amazing thing about Richard's work. It engaged you and grabbed you, without you judging it and without it having the distinction of high art or low art. It penetrates your psyche in a certain way, and I think that's true of documentaries, too. I think when you see a good documentary, it reaches you in a different way because you have a different expectation than you do with the suspension of disbelief when you come into a feature film.

Street art is also about the context and the city or the environment we're in. For this film particularly and for other documentaries, I find you're conjuring up a kind of a world around the story you're telling. You have to evoke that world and place your story in the context. You do that with the kinds of shots you do in the environment or you do it with archival footage. 

"I had no idea what story I was telling when I started. I just knew this is so compelling."

Then, that brings in the element of time. This story is a wonderful story because it takes place over a whole career. Street art is fabulous because it's there on the street and it changes and it evolves and things happen to it and people tag it. Or times change and then it has a different meaning to you and you see it in a different context.

NFS: In crafting this story, how did you balance the physical beauty of the artwork and mystique of the city with the harsh reality of your protagonist’s life?

Jacoby: I don't think we were after a mystique. It was like, let's tell the story of what this thing was. Then, I guess inevitably in the choices you make, you're showing some things that are gritty and the underbelly, how it was kind of brutal and dangerous and there were crime and drugs.

People romanticize drug use and art. One of the things we realized is that we're telling a story that shows what drugs really do in the life of an artist and what their destructive potential really is and how invasive and problematic they are. 

You make certain choices, whether it's in an interview or a piece of archival footage or music, which obviously evoke different feelings, and you try to create a balance. Fellini was my favorite director growing up; part of my artistic identity yearns for a kind of nostalgia that you undercut with a cruel truth about what's going on. 

NFS: It seemed that over the course of Richard's career, many people could be perceived as taking advantage of him. As doc filmmakers, we also toe this line: are we taking advantage of a subject or are we trying to honestly portray their story? How did you grapple with those questions?

Jacoby: You look at the film and you ask yourself, are these people helping him or are they taking advantage of him? Are they looking out for their own interests or are they looking out for his interests? I can say this almost without exception: all of these people have been able to maintain relationships with Richard over long periods... they fight with him, they break up with him, but they somehow come back into his orbit. They love him in a way, even if they feel that he's burnt his bridge with them. 

Richard Hambleton of 'Shadowman'Credit: Hank O’Neal. Courtesy of Storyville Films and Motto Pictures

Jacoby: I think there is a very obvious parallel with me. I started to shoot this film without money or a backer or anything. I've been spoiled as a filmmaker for years. I've had backing and I've had producers and I've had budgets. In this case, I was just thrown in there because I was compelled by the story. There were these scenes that were unfolding of his interaction with the dealers who were developing his career. 

I couldn't believe what I was seeing when I was there recording the camera. It fit the rule that my old film teacher told me years ago: if you're making a documentary and you're in a scene where the fact that you have a camera there is more interesting than what's going on in the scene, then you should pack up your camera and stop shooting. What was going on was so much more interesting to them than the fact that I was standing there with a camera that they basically ignored me. 

"I started to shoot this film without money or a backer or anything."

With Richard, it was a very, very slow, odd development of a relationship, where I was there and he ignored me. He kind of tolerated me and didn't ever, 'till very, very late in the process, even give consent and sign a release to be in a movie. I was like his dealers. I was invested in him. I'd spent all this time. I'd spent some money. I was emotionally connected, involved in the story. I didn't know, would I ever be able to do it? 

NFS: It's clear that Richard can be erratic and difficult. Were there instances that you thought you might not be able to make the film?

Jacoby: Oh yeah. We started filming in 2010 from September to March, off and on. Then the pressure of the shows and the money that was coming in for this new show got to be so intense that he was taking large amounts of drugs, or at least that's what was reported to me because I was no longer able to get in to see him, either. He wouldn't open the door, he wouldn't return phone calls. There was no access. 

NFS: Just for you or for everyone?

Jacoby: Everyone except his buddies who he was hanging out with. I thought oh, I'll never be able to make this film and I stopped. Then several months later, there was a big show of his work at a Cannes Film Festival AMFAR benefit. I was asked to edit what I had shot so far into some kind of a sizzle reel, to show at the benefit to celebrate his art. So I was pulled back into it to do that and I thought, I guess there's good material here and this is an interesting story and there really is some interest in his art. 

Then they came back to New York for the last big show at the fanciest gallery on Park Avenue. All of New York turned up for this thing and I was there and they were showing our little sizzle reel in the show and I was filming all these movie stars and hedge fund guys and people coming to look at Richard's art. Then a couple months later, he was in Rikers Island because he hadn't paid a jaywalking ticket.

He'd been dropped by the art dealers who were working for him. I thought, oh my gosh, this is an incredible story. I can't let this go. Then I was able to get a little bit of funding, but still not able to really establish a relationship with Richard again. He was off the grid. I kept trying. Then he got evicted from his apartment for not paying his rent. We came and filmed the stuff being thrown on the street and so we made contact with him a little bit and he saw that we still cared about his story.

Oren Jacoby's 'Shadowman'

Jacoby: Finally, like six months after the eviction, we found out he was sneaking back into the place where he'd been evicted. The marshals had put a padlock on the front door but he somehow had a key to a back entrance into the basement into some little, hidden space where he was still painting six months later. He allowed us to come back and I went into that space with him and did a little more filming with him painting. 

Then, I started to build up a relationship again with him. In the meantime, over those six months, we had started to contact all these people who had worked with him and had an emotional connection to his story, and we pieced it together. We realized it was too good to ignore.

NFS: Unbelievable. 

Jacoby: But even when I found him again, I'd call him and he'd say, "Come meet me at this time," and I'd get there. I'd knock on the door and he'd open the door a crack and he'd say, "Go away. Come back in a half an hour." Half an hour later, he wouldn't answer. We'd sit in the car and wait.

“Every impediment to your film is actually what helps your film and makes it better.”

NFS: How did you ultimately convince him to sign the release and officially participate? 

Jacoby: We reached a certain point where he began to trust me. I helped him with a few practical things, like cashing a check because he didn't have a bank account at that point. He just trusted me. He said, "Okay, well, I'll sign the release." It was never like a thing of like, "Oh, now I trust you and you're the guy to do this." It was like, "Well, okay. Sure."

Here’s a funny story that was the great epiphany with Richard. After this difficult relationship, he's now so excited that the film is at Tribeca. I went to talk to him last week and he said, "You know, I never thought you'd make this movie. I never had any confidence you could do it. You had that cheap camera. I kept thinking, he wants to make a movie, why doesn't he buy a better camera?" It's so typical of what people think about movies and documentaries.

One day we were there filming and a CNN crew came in with like one of those big dorky, broadcast ENG cameras. Then he was all impressed because he thought, "Oh this is real. This is television." In a way, it's a secret weapon. That's why he didn't pay attention when I started filming: he didn't care because it was just this small, handheld camera. We started out with this Panasonic HVX 200 in 2009.

NFS: What advice do you have from this experience and others over your career in dealing with uncooperative or difficult subjects?

Jacoby: Well, to go back to Fellini, I ran across recently an interview with Fellini from the mid-’60s or early ‘70s where he talked about his work and he said, "I discovered that obstacles are my friends." Every impediment to your film is actually what helps your film and makes it better. 

Credit: Hank O’Neal. Courtesy of Storyville Films and Motto Pictures.

It goes back to that—you have this nostalgia for a story and you go in with this rosy picture, and then you discover the truth and you strip away your illusions about it. You just roll with what happens and it makes it [more real] and true. What really happens is 10 times more interesting, and this is something that I, to some degree, always fought as a director. Early in my career, I was lucky enough to befriend Ricky Leacock, one of the founders of cinema vérité, and he saw my films and sort of encouraged me. He was always angry at me because I had this feature filmmaker prejudice against documentary. I was trying to have too much control.

NFS: How did you get over that impulse to control everything?

Jacoby: The first film I did was in a small town. I was saying, "How do I find a narrative to show what life was like in a small town?" So I made up a story. There were two friends who get out of high school and they're trying figure out if they leave or stay. One wants to leave and one wants to stay. I found two friends who played on a softball team where I was filming this town. They agreed to do this. It wasn't really their story. I showed this to Ricky and he said, "You've got to let go. Let the people find a story." I didn't trust it.

I went through my career and, often, I would have a story to tell and I would go at it and tell that story. Here, I didn't know what the story was. I had no idea what story I was telling when I started. I just knew this is so compelling. I have to film it and I have to come back and film what happens tomorrow. After several months, I still didn't know what the story was. Eventually, the story tells itself. Then, all the obstacles move you to the appropriate way to tell the story in the right narrative structure. 

Director Oren Jacoby filming 'Shadowman'Credit: Courtesy of Storyville Films and Motto Pictures

NFS: I've definitely found that to be true, again and again. It's hard to tell yourself that when you're facing the obstacle, but it's true.

Jacoby: Yeah, that's the thing with cinema vérité. I always wanted to make a cinema vérité movie but I half-resisted it. We were saved by discovering this wonderful cinema vérité footage of Richard's early career and early life—footage of him painting, both on the street and then the studio. Then, amazing vérité footage shot by his landlord, who was an amateur filmmaker and artist.

“You have to keep doing something different or you get stereotyped as making a certain kind of film.”

NFS: What did you learn about your own craft from watching Richard and seeing how he makes his work at all odds?

Jacoby: I think that goes back to what we were saying about the obstacles: you just have to keep going. You just have to be persistent. You have to let nothing get in the way. 

The other thing about Richard is that he has a sort of defined very strong stylistic signatures in his career, but he hasn't been afraid to abandon those or leave those for a while and go into another impulse and do something courageous, whether that's a good thing or a bad thing. I mean, it was devastating in some ways for his career.

It's something that I've always found important to sustain my interest as a documentary filmmaker. You have to keep doing something different or you get stereotyped as making a certain kind of film. Then you get kind of stuck in a not-creative mode or it's harder to make fresh films because you feel like, oh, I've done that before. I learned documentary quickly because the first few things I did where I made a name for myself were about Russia. I worked on a big PBS series about Russia and I went to the Soviet Union with the BBC and directed three films for them. Then I came back and people here said, "Oh, he's the Russia guy."

Then I started doing jazz films. I did a film about Benny Goodman and then they said, "Oh he's the jazz guy." You have to sort of keep reinventing yourself or you get stuck. Then you just make a film that's different and try to show you can do it.

For more, see our complete coverage of the 2017 Tribeca Film Festival.