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):

Postcard (1906):

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.
And for examples of modern reproductions of these stereotypes (literally), see these: one, two, three, four, and five.
For examples and discussion of contemporary “blackface,” see one, two, three, four, five, and six. Also, bugs bunny.





