I fear clowns and have studiously avoided them for most of my life, ever since a little one-ring Italian circus set up on a vacant lot a block from the house I lived in when I was a tot. I haven't attended a circus since and can only surmise what sort of unspeakable terror I experienced that day, its memory locked deep within the vault of repression that sits just east of my heart. Maybe, like Larry David, I was hit by a clown wielding a rubber mallet, or, like Carol Burnett, I was shot by a clown with a parasol gun. Yes, it turns out that many popular purveyors of screen and television comedy share my fear. Some even profess to hate clowns. I can't say that I do, because I've never been sufficiently intimate with any of them. Hate, after all, is the next-door neighbor of love.

I might have thought I hated paintings of clowns, though, had I given the matter enough thought. The clown genre has an artistic pedigree, of course—Picasso, etc.—but it primarily crouches in the netherworld of superannuated pop imagery, along with palette-knife bullfighters and hazy views of Place Pigalle in early spring. The figure of the clown, freighted with goo and ick, essentially embodies kitsch. Listen to Jerry Lewis: "When we think of the bulbous red nose of a clown, we think of laughter. When I think of that nose I think of one of the great sad clowns, Emmett Kelly. He made pathos an art to me." That's it—a straight shot from laughter to pathos without so much as a cough in between. But kitsch has lately been redefined. I'm old enough to have faint memories of clown paintings on the knotty-pine walls of people's rec rooms, but in today's world the genre is more likely to evoke John Wayne Gacy, the serial killer who posed in a clown suit with Rosalyn Carter and went on to turn out clown paintings from his prison cell. The horror once latent in kitsch is now its chief distinguishing feature.

Diane Keaton has a remarkable nose for the exact moment when throwaway cultural artifacts of the past cross the zeitgeist line to achieve posthumous postmodern significance, and she has led several successful recovery missions (Still Life most of all, also Mr. Salesman and Local News). And she has a great eye, which saves this effort from mere stinking irony. The paintings are all by amateurs or unknowns and were acquired at swap meets and thrift shops, and those that have dates range from the early 1920s to the late '70s. Most of them are disquieting in ways that seem intentional. Very few, that is, exploit the alibi of ineptitude, and only a handful are routine or generic. Affects range from the queasy to the purulent to the psychotic. Some of the clowns are sad, some are mad, and a number are bad bad bad. If I were to hang any on my walls it would have to be in a very special room I only entered a couple of times a year.

There are your traditional Pierrot Lunaire–type cultured and tortured Euro specimens, distinguished by their conical hats, who were assigned the costume by hateful cosmic puppetmasters. There are your traditional American failures who woke up at the end of a three-week drunk to find themselves in clown suits. There are scary humanoids who live in boxcars and subsist on bananas and whose makeup is permanent. There are intergendered wraiths who never leave their rooms and perform only for their tiny dogs (one of them, circa 1950, looks startlingly like Michael Jackson in a garlic-clove head wrap). There are various felons on the lam who have found the perfect way to disappear. There are clown voodoo dolls flung contemptuously across the room to land all floppy on a shelf. Most oddly, maybe, there are two or three perfectly sober Rotarians who just happen to be wearing red noses and outlandish hats, as if their portraits had been improved by some latter-day vandal.

The painting styles are primarily what you'd expect, post-Kokoschka or post-Modigliani or something, although the earliest work, a rendering by one Paul W. Tucker of a pensive harlequin against an unusual backdrop of cornfields and cumuli, looks strangely late De Chirico. The cover image, by a certain Don Barclay, appears almost photographic from a distance, with a faint city-lights scrim behind the clown that makes it seem as though he is guest-hosting on The Tonight Show. The last picture, a deadpan rear view of a pinheaded clown with large, circular ears, looks convincingly like a collaboration between Philip Guston and Mad's Don Martin. Interspersed among the paintings are texts of various lengths by comedic figures. The old school (Lewis, Phyllis Diller, Dick Van Dyke) reveres clowns; the moderns (Woody Allen on down) revile them; a few (Roseanne, Michael Richards) get all mystical. Some of them can write, notably Bobcat Goldthwait, whose dry account of baiting the clown lobby while promoting his movie Shakes the Clown is the collection's keeper. By and large the texts are little more than celebrity blurbs, but hey, that's lit biz. The book will make a great gift item, for grandparents, goths, and cultural-studies faculty alike!

Luc Sante's books include Low Life: Lures and Snares of Old New York (Farrar, Straus & Giroux, 1991) and The Factory of Facts (Pantheon, 1998).