The Guilt of Gold Teeth

A grinning skeletal figure in a black top hat stands at the center of this large canvas, arms stretched wide like a scarecrow, with red paint dripping down its body like blood. Painted by Jean-Michel Basquiat in 1982, "The Guilt of Gold Teeth" comes from the peak of his short but explosive career. The title sits scrawled at the bottom, and the whole surface swims with letters, numbers, dollar signs, and half-erased words. That figure at the center is often read as a shaman or trickster, a menacing presence that pulls together Basquiat's interests in death, wealth, and the way both haunt human life.

Basquiat started out spray-painting cryptic poetry on New York City walls under the tag SAMO before he ever picked up a canvas, and that raw street energy never left his work. The crossed-out text here is a signature move of his. He believed that covering something up actually made people look at it harder. Words like "PESO NETO," Spanish for net weight, nod to his Puerto Rican and Haitian roots and to ideas of value and what things are worth. Rising fast in the early 1980s art world, he died at just 27, which makes paintings like this one feel loaded with the very mortality that stares back from the skull's gold teeth.