You probably would never have heard of Billy Pappas if it weren’t for Julie Checkoway’s documentary Waiting for Hockney, which played at the just-finished Tribeca Film Festival. I certainly wouldn’t have.

I got a copy in advance from a film publicist looking to see what an "art critic’s take" on the film would be. As a documentary, it’s a solid entry into the follow-an-eccentric-around-and-see-what-happens genre. But as food for thought about the venerable, though still vital, question of the sociology of art, it got the wheels in my brain turning.

I’m going to go ahead and spoil the plot, to get to the point. The film centers around Pappas, an artist from Baltimore who spends eight-and-a-half years making a single hyper-hyper-detailed 14 x 17 in. graphite drawing of Marilyn Monroe’s face, based on the famous Richard Avedon photo.

The artist we meet in the movie is a preternaturally likable character, self-aggrandizing but also a straight-shooter. We glean that he studied drawing at the Maryland College of Art, and has been in a single New York group show, at the Society of Illustrators, but is otherwise a foreigner to the art scene. He seems driven by the desire to do something great, though he is self-conscious that, in his own estimation, he looks and sounds more like a bartender than an artist.

It was while he was working as a waiter that he met the architect Larry Link, a bowtie-sporting eccentric. Their talk somehow turned to art, and Link, impressed by Pappas’ enthusiasm, took him under his wing. What Link’s motivations were, it is hard to say, but you get the idea that he saw in Pappas a way to test out a kind of quixotic thesis about drawing.

Each month, Pappas received envelopes of money from Link as he labored to complete his opus, Marilyn, painstakingly elaborating the surface, millimeter by millimeter, working with lenses strapped to his eyes, at 20-times magnification. Once the piece was finally completed, he insisted that viewers wear surgical masks to look at the drawing, to avoid upsetting the delicate detail.

The movie begins after the actual process is finished. Pappas, we learn, has latched onto the notion that David Hockney is the person who will most understand his work, and we follow him as he attempts to set up a meeting with the famous painter who, he believes, will rocket him to the "next level."

For the first three-fourths of the film, as we approach the inevitable encounter with Hockney (which occurred in 2004), it builds Pappas up as an eccentric, if lovably mensch-like, genius. You meet his endearing family. We watch his mother, Cookie, bake a cake for Billy to take with him to Los Angeles for his meeting with Hockney. We meet his admirers, including "Brother Rene," a priest and high school principal, who accompanies him to L.A. and lingers in the background inexplicably. You listen to Pappas expound on what makes himself tick. If you are a half way cynical person, you start to roll your eyes at all the myth-making.

Then he meets Hockney. The encounter is unfilmed (apparently, the elder artist wouldn’t have it). Leaving, Billy and his entourage glow about how much Hockney loved the work, and how Hockney will become his champion. Portending bad things, however, we see the inscription Hockney left in an art book he gave his admirer: "For Billy with thanks and admiration for showing me your terrific drawing."

The film then cuts to four months later. Nothing has progressed for Pappas. Hockney won’t return calls. The filmmaker returns to interview Hockney’s cohort, Charlie Scheips, about what happened: "I was a little bit underwhelmed immediately," he reports of his encounter with the drawing. "Why did he pick Marilyn Monroe?" he asks, with obvious disapproval. He quotes Hockney’s impression afterwards: "’It’s still that fucking photograph.’"

Here, in effect, is the "art critic’s take." It’s bad. Unsophisticated. It is stinging to hear voiced exactly the jibes that may have floated through your head as the film was building Pappas up. Most damning is the casualness of Scheips’ dismissal: "There was a bit of naiveté there, the naiveté of not having been part of the art world." All the hot air pumping up the encounter drains from the film. Pappas’ drawing, pitched almost as a way to pry open the closed doors of art through sheer strength of effort, to "set the art world on its ear," in Link’s words, simply bounces off the institution, which moves on, impermeable.

Pappas owes $300,000 to Link for the years of support. Now 37, we watch him return to work as a bartender. He is heart-breakingly gratified as he counts out $40 from a shift’s work. The film ends with Pappas, sitting once more in his studio, in front of what looks to be the ragged start of a nude self-portrait. "It’s all done, except for the face," he explains, an admission that belies his eternally hopeful demeanor, telegraphing the trauma that the reception of the lavishly detailed Marilyn has inflicted on his ego. And that’s the end.

Glimpsed in the movie (its first appearance for the viewer stands in for the off-screen encounter with Hockney), Pappas’ image of Monroe’s face has a weird, undead quality that comes, perhaps, from the undifferentiated level of scrutiny across its surface. But since the drawing has a higher resolution than the photo it was based on ("10,000 DPI," Link brags), the artist’s creativity presumably really expresses itself at the level that film has the most difficulty capturing -- where the intricate physiognomic details are actually composited from observations of other models.

There is, however, the narrative surrounding the work to judge -- every artwork, of course, needs some kind of narrative to make sense of where it fits in with the world. It may be in the future hard to separate the meaning of Pappas’ opus from the story produced by Checkoway. In fact, long before Waiting for Hockney went to Tribeca, in 2005, the New York Times published an article on the film’s making that began with the questions: "How close is too close? Is there a point where nonfiction filmmakers, like their cousin journalists, face what Janet Malcolm would call that eventual ‘moral impasse’ of objectivity and exploitation?"

It is notable, then, that the more you think about the film, the less you get the man it is presenting. Like his image of Marilyn itself, Pappas appears, on the surface, very, very familiar -- he’s a guy from the neighborhood, and is nothing if not direct. However, the closer you look, the more confounding he becomes. Critic Lawrence Weschler, who figures in the film as the connector between Pappas and Hockney (and who has made a career exploring this kind of liminal creativity) is pictured musing of the drawing, "Is it art? Is it outsider art? Is it the most ecstatic endeavor in the history of scientific illustration? Is it insanity?" Hyperbole aside, this undetermined status sums things up.

It is not outsider art, first of all, not just because Pappas is so relatable, but because his intent is so clearly social. Marilyn is quite clearly in some kind of self-conscious dialogue with convention, sapping our ability to appreciate Pappas for eccentricity alone (the character we meet is more "quirky" than eccentric, putting on lipstick to use his own lips as a model for Marilyn, or goofily crafting an enormous lens to mail to Hockney to get his attention). Compare Pappas’ work to the intricate paintings of an authentic weirdo like Chicago’s Ivan Albright -- who, if not an "outsider" proper, seems to be part of a tradition of one -- and the latter’s creepy, melancholy world seems to justify the obsession involved. As to why Pappas selected his particular subject, all Waiting for Hockney gives us is a single line of dialogue from the artist: "I was thinking about taking a very famous person and trying to bring that famous face something it couldn’t otherwise have."

On the one hand, it would seem, Monroe’s face symbolizes blue chip "Art," courtesy Andy Warhol, so the choice reflects Pappas’ desire to insert himself into that world of high-visibility culture. On the other hand, the Avedon photograph, despite its cachet, has lodged itself far into the popular mind, beyond the cliquish art world. Marilyn is a popular icon. The choice encapsulates Pappas’ own particular, suspended, inside-outside position.

But the biggest mystery of the film is the one its title would seem to offer to explain: Why David Hockney? Why Hockney instead of, say, Chuck Close? Or Robert Longo? Or Marilyn Minter? Hockney’s name seems to have entered Pappas’ consciousness via Gary Vikan, the director of Baltimore’s Walters Art Museum and a sympathizer. But how Pappas connects his own work to the British artist is a mystery. The only clue is that it has something to do with Hockney’s interest in optics.

It’s not as if hyper-representational graphite drawing is totally beyond the pale for contemporary art -- a successful young artist like Karl Haendel (b. 1976), for instance, makes exactly that. Haendel had solo shows at L.A.’s Ana Helwing in 2003 and 2005, on either side of Pappas’ rendezvous with Hockney in the Hollywood Hills. What is missing is the irony towards the medium that marks Haendel as part of the club. On the contrary, it is Hockney as Traditionalist that seems to speak to Pappas -- he repeats a phrase he associates with Hockney, "To the Hand, the Eye and the Heart" -- despite the fact that his own work would seem to imply an appreciation of an almost cyborg-like precision. Billy Pappas is not outside convention, but he’s not in a comfortable relation with it either; he approaches it at a random, unstable angle, with no real place to land.

The upshot, finally, is that Pappas has produced a sort of abject image. Not just in the sense that Weschler notes in the Times article, that the closer one gets, the more its detailed attention to (for instance) hair growing out of pimples becomes inexplicable and repellent. There is no place for the work to fit into exactly. Guys like Pappas only get to be artists if they don’t want it. Again, Weschler from the Times: "Depending on how you look at it, he's insane or stupid. Or it’s a really enthralling adventure. And it is both; it goes back and forth between the two."

Pappas’ project provokes this kind of vacillating judgment for a simple reason: The codes that determine whether an artwork is "good" are attached to institutions and traditions which are semi-autonomous from the way people think of art socially, and more cramped. Pappas has clearly done something, maybe even something great -- you do leave the film wanting to see the work in real life -- it just hits a button that doesn’t plug into anything. Marilyn is a signifier in search of a signified.

I disagree with Weschler’s conclusion, which also seems to be the film’s conclusion, that Pappas should just be happy with the achievement of having made the drawing itself. Of course recognition is important. As a critic trying to evaluate such things honestly, you’re stuck with two contradictory positions. On the one hand, it would be great if the kind of specialized knowledge Pappas’ work seems to lack was more widely available (is there another field, besides the presidency, where having gone to Yale is quite so important to success?). On this level, Billy’s plight in Waiting for Hockney is an argument for the wider dissemination of the virtues of High Art. On the other hand, you wish that High Art was itself a bit more expansive and less specialized in the first place, and Waiting for Hockney is a tale of how limiting it is to define artistic value in those terms.

The film makes you think of all those people doing remarkable things in their basements, the dark matter of creativity without a proper name. But then again -- and at the same time -- as an esthetic-conceptual project, the more I think about Billy Pappas’ Marilyn the more the thought occurs to me: Isn’t pressing buttons in your head that you didn’t know were there exactly what "art" should do? I suppose it awaits an encounter with the actual work to know for sure.

BEN DAVIS is associate editor of Artnet Magazine. He can be reached at