Julie Checkoway's remarkable, tightly focused documentary Waiting for Hockney stars Billy Pappas, a Maryland art school graduate who was making ends meet tending bar when, prodded and in part funded by a makeshift support group of family, friends, and boosters, he decided to concentrate on trying to perfect his skill and create a masterpiece that he hoped would enable him to launch a self-supporting career as an artist. After discussing it with Larry Link, an architect who took it upon himself to help him focus his energies (in part by loaning him thousands of dollars over the years), Pappas decided to gamble everything on a pencil drawing--a portrait of Marilyn Monroe. Determined to capture the face in as much naturalistic detail as possible, down to the last pore and follicle, Pappas re-taught himself how to draw, and then spent more than eight years on the portrait until he was satisfied that he'd created the most precisely detailed, "realistic" depiction of the iconic face that a human hand could produce. Then, after giving some thought to how best to capitalize on this achievement, he set about trying to attract the attention of David Hockney. He convinced himself that if he could show Hockney his work, and the established artist embraced it as he hoped he would, that would be that: his career would flow from that moment.

Checkoway's background is in radio production. She's worked on This American Life, and it shows; the movie, with its interviews and at-home glimpses of agreeably off-center but basically average people, and its jokey use of vintage film clips and the use of pop songs and novelty music to pace it, is a pretty fair movie equivalent of a TAL segment, more so than most of the stories that the TAL staff produced for TV when the radio series produced its own spin-off Showtime series. It's become fashionable to knock This American Life, but Waiting for Hockney demonstrates just how satisfying the show's approach can be, and also how sly and prickly it can seem when applied to certain subjects. Right from the start, it's clear that there's something not quite right about Pappas's quest. He doesn't show any interest in or even any awareness of the idea of using art to express his consciousness or to create a new way if seeing; his conviction that the way to prove himself by showing that he can draw more "realistically" than anyone puts him in the same relation to the camera that John Henry was in to the steam engine, and the results of that battle were declared a long time ago. It's telling that, looking to have his artistry certified by someone whose opinion counted, he zeroed in on a very famous, very rich artist whose own work gave no reason to think that he would be sympathetic to his aims. Checkoway never tips her hand, though; for most of the movie, it's possible to get caught up in Pappas's state of mind and think that maybe things will work out the way he dreams they might. It isn't until the movie is nearly over that the viewer may realize the degree to Checkoway's strategy is about capturing naivete and self-delusion as it's experienced from the inside. The fact is that, although Chekoway's intentions are clearly affectionate and humane, there was probably no other way for her to tell Pappas's story without condescension leaking in, especially when Pappas's mother is onscreen, praying for the best for her son and analyzing snapshots of the great Hockney examining the fruit of her son's labors. ("You can tell that he's just tickled pink.")

Waiting for Hockney runs just 75 minutes, and it may seem slight as you're watching it, but it expands in the mind later, and gets you to thinking about different notions of the meaning of art and different standards of achievement. Tellingly, one reason that Pappas chose to designate Hockney his ultimate arbiter, not just of his drawing but of how he'd spent eight key years of his life, seems to have been that he knew how to track down the writer Lawrence Weschler, who was one possible means of contacting the painter. It makes perfect sense that Weschler, who has written about the Museum of Jurassic Technology in Los Angeles and and an artist who draws his own currency, would find Pappas's portrait fascinating on a Ripley's Believe It or Not level to which Hockney would most likely be indifferent. Interviewed in the movie, Weschler expresses his disappointment that Pappas has to take such an all-or-nothing approach--why he can't take any satisfaction in the simple fact that he spent eight years doing a remarkable thing. He has a point. But Weschler isn't the one who has to go back to tending bar.