Robert Colescott’s painting Death of Poet depicts a handsome man with an enigmatic smile staring contentedly through his memories of a mixed-up, yet satisfying life. In its way, it recalls the celebrated poet Paul Laurence Dunbar, who died in his 30s of acute alcoholism, the booze having been prescribed by a doctor to treat Dunbar’s coughing from tuberculosis.

At one point Death of Poet was vandalized, when some freak filled in the face of a white woman in the painting with black magic marker. There was always the element of a joyous vandal in Colescott, who died last night at the age of 83. His internalization of the caricatures with which White America tarred its black supplicants made a lot of liberal types uneasy, in a reaction similar to those towards Langston Hughes’ street philosopher Simple, Louis Armstrong’s Sleepy Time Down South or the broad comedy of Moms Mabley or Pigmeat Markham.

Colescott embodied the old saw that you gotta laugh to keep from crying because it hurts too much inside. Thus, tragedy was constantly peeking into his broad-brushed satire, like the sideways red head of a woman in his masterwork The Emergency Room at the Museum of Modern Art. The wide berth of his humor was a way of distancing himself from the presumptions and assumptions of his viewers: Crow in the Wheat Field at the Corcoran Gallery garishly depicts a ghostly van Gogh observing a black painter drawing a couple of dancing skeletons.

As with the rest of Colescott’s work, it’s hard to make any rational sense out of his vision, other than to drown in a kaleidoscopic swell of lushly colored pain. Colescott’s truest living descendant is William Pope L., the man who crawled up Broadway in a Superman suit and otherwise dramatizes the whole ridiculousness of being black in America. All those eyes looking at Barack Obama are staring out of a Colescott canvas: ugly laughter on one side of the seesaw balanced by a singular dignity on the other. What future circumstance will tip the scales?

CHARLIE FINCH is co-author of Most Art Sucks: Five Years of Coagula (Smart Art Press).