By Stephen Saito

[For complete coverage of the 2008 Tribeca Film Festival, check out IFC's Tribeca page.]

Last year, when New York magazine celebrated Richard Avedon's portrait of a pensive Marilyn Monroe by publishing reinterpretations of the famous photograph, they probably didn't think to ask Billy Pappas for a contribution. A waiter and busboy from Baltimore, Pappas devoted almost a decade to painstakingly recreating the Avedon snapshot as a hand-drawn sketch, a labor he called his attempt "to take a drawing where Lindbergh took the airplane."

Pappas was brought back to earth when he decided it was time to introduce his piece to the art world. After rounding up a motley band of supporters to find a way to showcase his work, he settled on trying to get an evaluation from David Hockney. One would think that with a title like "Waiting for Hockney," the feature debut of director Julie Checkoway would be about Pappas' pursuit of the famed artist, but that's only half the story. What Checkoway discovered was a story as riddled with complexities as Pappas's intricate drawing of Monroe. While the documentary evokes the age-old discussion of what is art, "Waiting for Hockney" also asks the far more fundamental question of what it means to be successful. Recently, I asked a few questions of my own to Checkoway, a former producer for NPR's "Morning Edition" and "This American Life," whose film makes its world premiere in the Discovery section of this year's Tribeca Film Festival.

Why did Billy's story appeal to you?

I felt like I was meeting someone from my own family. I came from a big ethnic working class family that had aspirations of greatness as well, and when I met Billy, I was like "Oh my gosh, he's my brother or my father." And when I met his family, I thought "These are my people. I'm going to have to make a film about them." I'm obsessed with the way that suffused through our whole culture is this whole notion that you can come from nothing and become something, and that's not a bad thing. That's an American dream. But the thing that bothers me about contemporary culture is this notion that many of us walk around thinking that someone is going to save us from our ordinary lives. It's this "American Idol" syndrome.

I was talking to someone the other day who said he thinks the reason is that we've lost a sense of a road map for how a life can be lived, so all we have is this trajectory of being invisible and suddenly being incredibly visible and fixed and fine and redeemed. When that happens for Billy, I was really dubious, but I was also happy for him. At the same time, I'm almost 45 years old and I've had many of my own career ups and downs and dreams, so it'd be impossible for me to tell a story about fame that was in some way simplistic, because I think fame is really scary.

Since you'd never made a film before, how did this idea become a film?

I was doing freelance work for NPR in Baltimore when I encountered this story. 30 hours of audio later, I realized I had something that wasn't going to make it into a 20-minute slot and that was raising all these bigger issues and that was very visual, but I was in denial. My older brother, who's one of ["Waiting for Hockney"'s] producers, said to me, "You know, you really need to think seriously about whether you could make a film of this, because I'm telling you, it's a film." I was like, "Don't tell me that." [laughs]

It felt very assured for a first film, including your use of archival footage to illustrate how Billy's sketch evolved and his eventual pursuit of David Hockney. How did that come about?

I wanted to use the vintage footage to give the film this feeling of a caper, like it was antique in a way — not the film, but the behavior of these people seemed out of another century. It's like the 1930s — we're going to put a show on in the barn and, gosh darn it, we're going to be famous! That was what I wanted to get across — this hopefulness about America and "We can do it!" One of the things that didn't make it into the film [was Pappas's patron and primary supporter] Larry Link saying, "I'm the best mind of the 19th century," because he is completely retro in his desire to go back to the pencil. He's this dandy figure from the 19th century, and Billy is Horatio Alger, and it was stunning to me how they were still living out this story: "I'm going to come up from nothing and I'm going to be an oil baron."

As someone who needs to tell a story, was there ever a conflict with Billy and his team, since they might have a different agenda in promoting their artwork?

There are two questions in what you're asking and they're both good questions. The first is they totally used me [laughs], but because they're not stupid. There was a point at which we had to make it clear that the film was not an infomercial for Billy's piece. What was hard was that I loved Billy so much and I loved the piece — for journalistic integrity, I had to pull away from him and he had to pull away from me. I remember him saying "Look, I get it. My art is this portrait and your art is the film, and you just have to do your thing and I have to trust that maybe you'll present me well." And I didn't know if I was going to present him well.

There is a way in which, certainly, he and his team considered the film to be an advertisement for a portrait, but it's more complicated than that. He's sort of tied his hopes to the launching of the film to the reveal of the portrait, which is going to happen in New York the night of the [Tribeca Film Festival] premiere [on April 24th]. He waited for Hockney. Now, he's waiting for "Waiting for Hockney."

Has Hockney seen the film yet?

Yeah, he's been great. Initially, he didn't want us filming. Then he didn't want anything to do with the film at all. Then, of course, we had a lot of images of his we put in, and we started to vet them for public domain or fair use and finally our partners in New York said, "Just show him the film." And they showed [Hockney's former assistant] Charlie Scheips the film. He loved it and took it to London and showed it to David Hockney, and David Hockney will not endorse the film, but he adored [it]. Being a working class guy himself who came up from humble origins, the film touched him, and so he gave us full permission without having to pay to use images. He will not endorse it, and I completely respect that.

This film took four years to complete, including a hiatus for the birth of your daughter. Do you think that the changes that you went through over that period of time impacted the final cut?

Absolutely. Billy's narrative arc is not unlike my own. He practically bankrupted himself making this one piece of art. I wouldn't say I totally financially bankrupted myself, but I strained my family and myself for at least half the [length of] time that Billy did. There's a way in which his expectations and his desire for the portrait to come out and be seen and loved, and how he then responds to what happens to him, [that] made me that much more realistic about this being just a film. This whole film is about things being just what they are and not more than that. Was I inspired by him? I wouldn't do what he did, but in a way, by taking on something I've never done before, I certainly put myself in the same position. At the end of the day, I have kids, a husband, a house, a family, a full-time job — Billy, you know, he has the portrait. At one point, Billy said to me, "Julie, who would've thought it'd take you half as long to make this movie as it took me to finish 'Marilyn'?" [I said,] "It isn't funny. Billy." [laughs]

[Photos: "Waiting for Hockney," Littlest Birds Films, 2008]

For more on "Waiting for Hockney," check out the official site here.

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Jonathan Santini

very interesting stuff...