11. Michael Ray Charles, The Pursuit of Happiness from the series Forever Free
It’s easy to forget how edgy Michael Ray Charles’ Forever Free paintings were decades ago, when the art market was not rewarding black artists for making art about “the black experience” to the extent that it has in more recent years. Charles’ minstrel character, based on advertisements and pop culture, inspired Spike Lee’s 2000 film Bamboozled, about a blackface TV show that becomes an unexpected hit. (Charles served as an advisor on the film.) Crisp and graphic, this deliberately beaten-up image questions the hollow promises of consumer culture, to say nothing of the Emancipation Proclamation and the Declaration of Independence.
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