In 1987, after ten years of appropriating photographs culled from popular culture, Richard Prince began his first forays into a dialogue with high art culture as a source with these initial paintings. Prince began making these small paintings as works for himself, not for the public, before engaging on a long series of paintings that continue to evolve today. These first paintings are rare and seminal and Five Jokes Painted to Death is an important example.
Five Jokes Painted to Death plays upon the tradition of painting as a labored and heroic exercise. Prince uses the joke to subvert the reverence of the viewer for the paintings while painting itself sometimes obscures and subverts the joke. This series of four paintings is unusually complex for such early works. The first canvas contains one joke, partially obscured, while each of the following canvases has a joke which has been painted over and then overlaid with another joke that has been partially painted over. In this way Prince creates tension between the joke subverting the painting and visa versa. Finally, Richard Prince intended, as part of the joke of the series as a whole, to leave out a fifth canvas.