Minstrelsy is a form of entertainment, popular from the 1830s till the early 1900s in which white, and later black, people painted their face black and performed a caricature of blackness. The images below (borrowed from Jim Crow History and Wikipedia) are original advertisements for minstrel shows.
Haverly’s United Mastodon Minstrels (circa 1877):
Oliver Scott’s Refined Negro (1898):
Al W. Martin’s Uncle Tom’s cabin (1898):
Wm. H. West’s Big Minstrel Jubilee (1900):
For more caricatures of black people in U.S. history, see these posts: one, twp, three, four, five, six, seven, eight, nine, ten, eleven, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, and twenty.