In the documentary Guest of Cindy Sherman, a confection of reality-show, confession, and celebrity gossip, we become acquainted with Paul H-O, the film’s narrator, subject, and co-director. Paul’s goofy New York cable-access show suddenly gains buzz when the famed feminist artist Cindy Sherman grants him an interview — and then she does several more, after years of avoiding interviews with journalists. “Gallery Beat,” Paul’s amateurish man-on-the-scene videos of his attendance of various New York art openings, oddly proves to be an outlet where Cindy is comfortable talking about herself and her work. She flirts with Paul, too. After she and Paul move in together, her career takes off. Something about Paul H-O — his plainness, his frank admiration of her — seems to liberate a somewhat guarded yet undisguised Cindy Sherman to shine in front of the camera instead of behind it. The rising tide of her popularity seems at first to lift both their boats, but his, not so much.

Part of our coverage of the Starz Denver Film Festival
Paul H-O, as the narrator, is not always unsympathetic; when he is, it’s because he lacks finesse with people. Yet he persists in filming, showing what’s in front of him, including the people around him, even showing how much they despise him or how superior to him they feel. “Oh, look. The barbarian is at the gate,” says one arrogant artist, staring into the lens with real vitriol, and you wonder what Paul must have done to arouse such ire.
Yet Paul’s humble efforts make you consider people and their relative worth as he describes the process of “going from the guy everyone wants to talk to to the guy almost nobody wants to talk to.” Turns out it is a rough job, being boy toy to Cindy Sherman. You don’t even get your own namecard; it’s just “Guest of Cindy Sherman” now. Also sucking air out of Paul’s room are an array of luminaries in many fields who dot the new couple’s landscape: writers, artists, filmmakers, film stars, publishers, moguls of all stripes, and jack-of-all-trades Steve Martin. Paul’s outsider status is his own limiting factor here; Paul is forever consigned to surfaces. In part it’s because no one sees him as an artist, and he’s also always behind a camera, never getting to know anyone better. Cindy and others complain: “I won’t do this on camera. It’s private,” she says. “Turn it off. No, it isn’t off! I see the red light!” (Moral: Never try to trick a visual artist.)
Paul plods along pursuing his passion for years, but drops “Gallery Beat” soon after he starts living with Cindy. A while later, he attempts to start a new version called, “Artlike,” but that goes nowhere.

Jeanne Tripplehorn, right, and guest
Paul opens up to some radio-show hosts, who invite him in for an interview on their show. WFMU radio’s Kelly & Bronwyn grill him: “So you knew she was famous before you moved in together, but now it’s not okay?”
He whines, “I know what it’s like to be the wife, now.”
They say, “That’s good! Why is it okay for women to experience this and not men?” They dub his dilemma “famous-girlfriend syndrome,” and Paul has what’s referred to in the publicity world as a platform for his position.
Stamps of approval come in the forms of brief interview segments agreeing with Paul’s central thesis featuring the actress Molly Ringwald and her husband, a writer whose name I didn’t get (See? It happens.), and David Furnish, partner of Sir Elton John. Furnish relates his humiliating tale of attending an event where he was relegated to a table by the door to the kitchen two rooms away from his extremely significant other. (How it went down: David lost it, Elton said, “I’ll fix it,” Elton spoke with their host, Uma’s card was moved to another table, and a hastily scribbled place card was whisked into David’s new spot.)
Because the graceless Paul H-O features so prominently in it, I kept fearing the film would lapse into something clumsy, something that would make me want to stop watching the film before it was over. But the narrative surprised me at those moments by pulling back from his particular brink of clutziness, and the story about this odd couple kept me on edge. Other tensions kept pulling me in, too: the tension between the sunny, pert faces of the “real” Cindy Sherman and the desperation in her portraits, and the class tensions that course through most scenes. Thanks to films like Junebug, we’ve all heard of outsider artists, but Paul H-O is outside everything here. He’s not a buyer or an agent or an artist. Paul becomes ever more conspicuous on the scene for what he is not; in the end, his claim to his role as partner to an artist is just about all he has left.
There was an abrupt moment at which I realized that the documentary I was watching was itself the culmination of the director/subject’s ambitions and the very documentary being discussed on camera. That moment signaled Guest of Cindy Sherman’s breaching of a line between self-reflexiveness and solipsism I had been expecting it to creep over. Make no mistake about it, that reminded me: this is an indie film, “hopelessly public access” at times, shot on various formats of video, half reality show and half documentary.
By the end of the film, it’s easier to find compassion for Paul as a regular guy with a passion for sticking his camera in the face of the art world but one who missed out the big financial wave of the last decade that jacked Cindy Sherman’s art prices into the stratosphere and allowed her to buy a house in the Hamptons but ultimately left him beached and picking sand out of his teeth. Yet Paul seems to remain upbeat if not always inspired about his prospects regardless of what is happening around him. He’ll find his way.
It’s harder, though, to fathom the appeal of the “supercharged” art scene, watching Julian Schnabel rip Paul a new one for doing his humble thing: “Now that I’ve seen your show, I think I should have been ruder before,” he spits at Paul’s everpresent camera. One agent’s phone rant about the dramatic cascading effect of her client’s five-minute interview with Paul is titillatingly awful (“Damien has a fitting at Armani, he rescheduled with Madonna because of your interview, and he was supposed to have tea at The Pierre with Gwyneth, but now....”), but when John Waters pops up to defend elitism in art, adding, “I think art for the people is a terrible idea,” I think those people probably deserve each other.
Paul is like a teenager finding his voice; you keep flinching at the awkwardness of it all, but you can’t help rooting for him. He is at his most perceptive when he is quizzing Cindy on her feelings about the characters in her portraits. “Do you like them, or do you not like them?” Habitually, she doesn’t reveal a lot, and turns the questions back toward him.
In the end, is there more to Paul than this story of his close brush with fame and fortune? We may have to wait for his next entrepreneurial effort to find out.