A new documentary film, Guest of Cindy Sherman, which premiered in theaters at the end of March, provides a behind-the-scenes look at the artist and the 1990s art world, as seen through the eyes of its star and co-producer, former artist and dedicated surfer Paul Hasegawa-Overacker. Centered around his romantic relationship with Sherman, the story begins in 1993 when Paul H-O, as he is familiarly known, got a video camera and launched his public-access TV show “Gallery Beat.” An irreverent and well-informed program, Gallery Beat featured H-O, along with A.i.A. staffers Cathy Lebowitz and Walter Robinson (who is now at Artnet) as they went to openings, chatted with artists, visited studios and humorously tracked all manner of goings-on in the New York art world. Throughout the documentary, such notables as David Ross, Roberta Smith, Jerry Saltz, Judd Tully, Charlie Finch, John Waters and Eric Bogosian, along with assorted friends and family, provide commentary about H-O and his TV show, his relationship with Sherman, and her work.

As H-O says in the film, Gallery Beat launched in the recession of the early ’90s, when “the art world was really friendly because everybody was pretty much broke” and half the galleries were going out of business. Viewers get to revisit the scrappy start, in 1994, of the Gramercy International Art Fair (at the then-downtrodden, now swanky Gramercy Park Hotel), for example, before it morphed into the Armory Show, and watch Tracey Emin and Jay Jopling, relatively unknown at the time, hang around their hotel room. As the film progresses, and the art world begins to overheat with money and celebrity, dealers and artists become less cooperative with the Gallery Beat crew and less tolerant of H-O’s in-your-face antics.

Along the way, H-O meets Cindy Sherman. After many months, because she is intrigued by H-O, she accepts his request for an interview. Following a series of flirtatious, squirm-inducing on-camera encounters with the paradoxically camera-shy artist, they begin to date, and H-O eventually moves in with her in 2000. He lives the high life for a while, attending A-list parties and jetting out to L.A. with the art-world elite on Eli Broad’s private jet. Soon enough, however, as his first TV show flounders in 2002 and a new one fails, the film becomes more about H-O’s bruised ego. After five years, as H-O and the relationship begin to crack under the strain of his feelings of inadequacy, he engages in avoidance through surfing. A pivotal moment for H-O was attending a gallery dinner at which, seated several tables away from his girlfriend, his place card read “Guest of Cindy Sherman.”

H-O then does a little soul-searching. He interviews other people on the topic of being a +1, including Eric Fischl and April Gornik, and Elton John’s husband David Furnish. Yet even after he is “downsized” in 2006—we see him inflating an airbed in his humble new digs—his admiration for Sherman never wanes.

Sherman, who had final approval on the film, issued a statement disavowing her role in its making when it screened at the Tribeca Film Festival last summer. She said, in part, “I apologize to all those who participated, thinking they were doing me a favor in giving interviews and otherwise assisting in the fabrication of this film. Against my better judgment, it was clearly unwise to cooperate with the project at its inception.” She needn’t worry. She remains an endearingly enigmatic figure whom H-O never topples from her pedestal. And H-O manages to weave in an intriguing overview of her career, particularly its early days. The film was completed before the current economic crisis, and H-O seems prescient when, lamenting what the art world has become, he says in a voiceover, “something’s gonna happen.” And then he surfs off into the sunset.

[Guest of Cindy Sherman, aFilmlike production co-produced by Tom Donahue, screened at Cinema Village in New York and at the Santa Fe Film Center, Mar. 27-31, and will appear on the Sundance Channel in coming months.]

For more on "Guest of Cindy Sherman," visit Art in America's coverage from the premiere party held at Tailor on Tuesday, March 24th.