When Paul H-O, a celebrated figure of the 1990s New York art scene with his popular public access TV show “Gallery Beat,” got the chance to interview internationally renowned, press-shy photographer Cindy Sherman, he had little idea that their growing romantic relationship would ultimately lead to a feature documentary. Fifteen years-in-the-making, Guest of Cindy Sherman, which Paul H-O co-directed with celebrated documentary editor Tom Donahue (Keep The River On Your Right: A Modern Cannibal Tale, Naked States), is a piercing look into the New York art scene as well as a fascinating exploration of the nature of celebrity.

Featuring interviews with John Waters, Danny DeVito and other notable celebrities in the art and entertainment world, Guest of Cindy Sherman is sure to entertain both art fans and documentary lovers. Just before the movie’s release on March 27, 2009 in New York and Santa Fe, MM spoke with co-directors Paul H-O and Tom Donahue about their much buzzed-about collaboration.

Kyle Rupprecht (MM): Paul, what compelled you to make a documentary about your relationship with enigmatic artist Cindy Sherman? What makes her such a fascinating figure of the art world?

Paul H-O (PH): It just so happened that I was in a relationship with Cindy at the time—and the event (or incident) that compelled me to pen the story, Guest of Cindy Sherman, was a real dinner party I had attended with Cindy at the time. We’d been together for a few years and I knew the people who’d done the party and they sat me at the place that named the film (and I had a slight identity implosion).

Cindy is fascinating figure in the art world because she is so well-known and influential, yet famously press shy. Not only are she and the Metro gallery tight-lipped about Cindy, not even her assistants had seen her work in the studio. That makes her a very desirable subject for the press. (Think Tom Pynchon or J.D. Salinger.)

MM: Tom, at what point did you become involved as co-director of the movie?

Tom Donahue (TD): In late 2003, I got a call from Spencer Tunick (the subject of two docs that I edited: Naked States and Naked World). Spencer told me about “this guy, Paul H-O, who is sitting on some amazing footage.” He thought that if Paul and I teamed up, maybe we could figure a way to do something with it. So about a week later, we met. I screened highlights from the “Gallery Beat” archive and, of course, Paul’s interview material with Cindy and saw that there was something there. So it wasn’t long after that we decided to team up as co-directors and try to see if we could make something together.

The problem was that even though the material had a lot of possibilities, it wasn’t enough material to make a doc out of. There was an incredible first act (zany art world/boy meets girl) but that was it. About a month later, Paul had something happen to him that sent him into a psychological tailspin. And from that, we found our story’s center (and the title of the film). We built on it from there, conducting about 70 interviews and continuing to follow the events in the relationship and the art world over the next four years. We were working toward a finished product having no idea how it was going to end.

MM: You’ve worked as editor for over 10 years on many acclaimed documentaries. Did you find the transition from editor to director to be a difficult one?

TD: No, it’s not difficult. Having a comprehensive understanding about how a story is constructed is essential to the skill of directing. And that’s what you learn as an editor. Having been an editor for so many years, I was acutely aware of the material I needed to get in order to properly tell the story. Though, of course, like most docs (no matter how well directed), so much of it was still created in the editing room.

MM: Guest of Cindy Sherman revolves around the New York art world of the 1980s and ’90s. How do you feel the art community has changed since then?

PH: I was an artist until 1993, when I decided to quit being an artist. I said, ‘I am no longer an artist’ and the feeling was liberating. Of course I had discovered that cable TV enabled me to transfer that energy into a show I called “Gallery Beat.” I knew right away I wanted to do a humorous travelogue into the belly of the beast: NY’s gallery jungle.

The art community has changed more than once since I began reporting on it. In the ’80s it was East Village and art, performance and music all mixed up in a series of funky venues. In the ’90s the art scene moved to SoHo and the galleries were more upscale, but reflected the loft life artists created there. By the end of the ’90s the entire gallery system had up and moved itself into an artist-free zone in West Chelsea. It became larger, whiter and the austere shopping mall it is now that is only superseded by the major modern art fair—the ultimate superstore of art object knickknacks for rich people.

MM: What were some of the hardships along the way?

TD: I would say the breakup of the relationship threw the biggest wrench into the works. Though it also gave us our ending.

MM: What’s the best piece of advice you can offer aspiring documentarians?

TD: Find a great subject you can get access to and go for it. Don’t stop until you have the story, however long it takes. And get a great editor.