In the rear of Jessica Fredericks’ semi-basement Chelsea space, there hangs—or hung, during the gallery’s John Wesley miniretrospective this winter—a modest-size painting from 1976 entitled Princess Sacajawea Crossing the Snake. It depicts, in Wesley’s never-varying technique of flat shapes, delicate black outline, and matte, chalky color, a female in a leotard or bathing suit, seen in midair from behind, doing the splits, her arms extended groundward. The background consists of five horizontal bands: pale blue sky at top, then green distant “forest” (its upper edge is ragged, hinting at faraway treetops), next pale green ground on the far side of the river, the blue river itself (presumably the Snake), and, at the bottom, pale green field again (the ragged upper edge indicating grass along the near bank).

The question that immediately arises with this picture—or any other Wesley picture—is not What does it mean?, but Why did the artist want to paint it? There’s something in Wesley’s combination of rote, coloring-book method and deadpan approach to semisurrealist subject matter that makes you want to know more about his biography, personality, and motives and not a whole lot more about the iconography itself. Wesley is special in this way; you don’t ask the same of paintings by other “flat” painters. Who the hell wants to know what motivated Alex Katz to paint a particular picture? Or even Roy Lichtenstein? Wesley’s paintings are like little crime scenes: while the deeds done in these vignettes are certainly not run-of-the-mill and perhaps even macabre, they’re not nearly as fascinating as the possibility of catching the perp and making him confess.

Maybe there’s a clue to Wesley’s motives in Princess Sacajawea’s content, or in the iconography of the whole show. But, God, this can get complicated. Anybody can have any reason for painting anything. Some have simple reasons for painting simple things (Fairfield Porter, for example), simple reasons for painting complex things (Rene Magritte), complex reasons for painting simple things (Gerhard Richter), and complex reasons for painting complex things (Salvador Dali). Moreover, Wesley’s images are so varied, and weird: try a wall filled with gouaches depicting, in part, George Gordon Lord Byron as a Cranky Sailor, 1989, a nude Blondie apparently about to administer a blowjob to a nude Dagwood on a bed, Dagwood alone in a bathtub (the piece’s entitled B Musing about Charlotte Corday and the Course of European History, 1974), and a waterspout and empty dialogue balloon manifesting themselves in the sky above an ocean. What’s here doesn’t tell me anything except that I’m probably in the presence of a pretentious autodidact who’s got a generous enough sense of humor to make fun of pretentious autodidacticism. Three bigger canvases with simpler, visually more abstract, and less quirky content (a patterned yellow sofa in front of a window through which can be glimpsed the sail on a distant boat; a closely cropped, Titanic-esque ship plowing through gray water; and a fruit tree that looks more like Ken Price’s work than Wesley’s) imply mainly that the artist is interested simply in playing with the look of everyday things.

On then to the actual bio: Wesley was born in Los Angeles in 1928. His widowed mother bounced the family around from home to home and even put the young John in an orphanage for a year, reclaiming him once she remarried. After high school, Wesley couldn’t afford to be a full-time college boy, so he took a job as an aircraft riveter before laboring for five years, beginning in 1953, as an illustrator at Northrop, the defense contractor that produced, among other weapons, the XB-47 “Flying Wing.” It was during this half decade that he became interested in painting. In 1958, he was included in a local juried show, and the rest, as they say, is history. At the relatively ripe age of forty-three, he took his first trip to Europe, where he lived for some time with his second wife, Hannah Green, a writer. (He was briefly married to the Minimalist painter Jo Baer.) Green died in 1996, and Wesley now spends most of his time in New York. The story of Wesley’s life has amounted, in short, to the kind of slightly skewed narrative that indicates an artist, but it’s not exactly something out of Dickens.

Over the years, Wesley’s cartoony pop has had a cultish following and captured the attention of any number of critics: Brooks Adams, Peter Frank, Ken Johnson, Michael Kimmelman, David Pagel, Peter Schjeldahl, Sanford Schwartz, John Yau. (Wesley’s fey eroticism seems to appeal—surprise!—mostly to guys.) I think it’s the emotional blankness that attracts the critics. As for me, I’m something of an unreconstructed formalist in the sense that I believe, in the approximate words of the old Little Richard song, that it ain’t what you do, it’s the way that you do it. And I generally like Wesley’s slightly imprecise graphic precision (he probably had a real love-hate relationship with that Northrop job) and loopy pictorial codification. I also like the constant buzz of sex (in the daytime, between people like the Bumsteads, in clean little houses). But at bottom, Wesley seems the painter-equivalent of photographer Garry Winogrand, who once said that the reason he photographed something was to see how it would look photographed. Wesley dreams up his images, then puts them down in paint to see what they’d look like on a canvas.

Then again, as a little kid I lived in a pale green ticky-tacky house under the test-flight path of Northrop’s Flying Wings. When they would go over and (according to my mom) rattle the dishes inside the house, they looked real neat to me. But also, down deep, very, very scary.

Peter Plagens is a painter and art critic for Newsweek. With this issue, he rejoins Artforum’s masthead as a contributing editor.