NEW YORK (Modern Painters)—"Freedom produces jokes, and jokes produce freedom," said philosopher Jean-Paul Richter as quoted by Freud in his 1905 study of jokes. It is a simple, seemingly innocent conceit, but also misleading. To tell a joke, one must follow a script—the jokes success lies wholly in the delivery. And the idea has a sinister undertone. Freedom, after all, does not necessarily equal benevolence, and jokes can be cruel.

In a work that appeared in last year's Whitney Biennial, there were 24 30-by-40-inch prints, unframed and pinned to the wall in a grid; each showed a pixilated blow-up of a young man standing in front of a curtain, shaggy blond hair hanging in his eyes. He is posed differently in each, sometimes holding what appears to be a hand puppet, his figure partly obscured by collaged cutouts and doodles in tempera paint, graphite and magic marker.

It is a subtle, black-and-white piece, and, when juxtaposed with some of the more bombastic work in the biennial, it was easy to overlook. But its unassuming nature is part of its appeal, and on closer scrutiny the gridlike arrangement, similar to a storyboard for a film, congeals into an absorbing study of narrative. Yet it is impossible to determine any sort of trajectory.

The title offers a hint, So There's This Pirate . . . , but the ellipses inform us that, although the performer is likely telling a joke (one that seems vaguely familiar), we'll never know the punchline. By depriving us of the outcome, the piece keeps us in a perpetual state of limbo, delaying any possibility of satisfaction, or, to return to Freud, freedom.

The performer in So There's This Pirate . . . is artist Jay Heikes, based in New York and Minneapolis, and only upon further investigation does one learn that the images are stills derived from a video he made in 2005.

In that video, which is not part of the artwork, Heikes tells a joke involving not only a pirate, but also his loyal if insubordinate companion, a parrot. The video provides Heikes with raw material to make the Pirate drawings, and the artist is continually embellishing and adding to the joke and recording the results on video to generate new stills, which in turn bear new graphic embellishments.

"By telling the same joke over and over, I've realized its rigid structure allows me to find totally new directions every time I make the delivery—like the splats and circles that relate to art movements such as Pop Art and Expressionism," Heikes stated recently in an exhibition brochure for a group show at the Walker Art Center. The latest iteration of the piece, which will be on view in a group show at Marianne Boesky Gallery in New York this October, includes a bit of pyrotechnics involving a candle and some spray adhesive.

Having already invoked Freud, it would be easy to slap a psychoanalytic reading on another work by Heikes, the 2005 sculpture The Hill Upstairs, which is installed in an administrative office at New York's P.S. 1 Contemporary Art Center.

It might take a few moments to find the piece, since it hangs overhead. It consists of a section of drop ceiling that measures roughly 25 by 30 feet and projects about two feet down from the actual ceiling. The tiles are pockmarked and flimsy—as they are in all drop ceilings—but a faint pink fluid seems to have seeped into the porous material.

Since the ceiling is false, its rigid structure intended to conceal something unsightly (wiring and heating ducts, for example), the leak might seem an ugly and potentially menacing intrusion. But that kind of interpretation would disregard the formal qualities of The Hill Upstairs, which would be a shame.

The stain, derived from coffee and beet juice, spreads over the cheap, oppressive tiles to surprisingly sensual effect, and it lends them a weird kind of dignity; given the work's reference to Minimalism—the repeating forms, the grid—its use of materials evokes the way that Donald Judd's sculptures elevated aluminum and plywood to the same status of precious materials such as marble.

But more than Minimal art, the comic seems, at this point in Heikes's development, his primary inspiration. When Heikes adopts the comedian as an alter ego, the connection becomes inevitable between the Laugh Factory and the art gallery: the stand-up comic stands in for the artist presenting his work to the public via talks, symposiums, statements and interviews.