The picaninny (It is also spelled pickaninny and piccaninny) was the dominant racial caricature of Black children for most of this country's history. They were "child coons," miniature versions of Stepin Fetchit. Picaninnies had bulging eyes, unkempt hair, red lips, and wide mouths into which they stuffed huge slices of watermelon. They were themselves tasty morsels for alligators. They were routinely shown on postcards, posters, and other ephemera being chased or eaten. Picaninnies were portrayed as nameless, shiftless natural buffoons running from alligators and toward fried chicken.

Source: Dr. David Pilgrim, Professor of Sociology
Ferris State University
She was one of the blackest of her race; and her round, shining eyes, glittering as glass beads, moved with quick and restless glances over everything in the room. Her mouth half open with astonishment at the wonders of the new Mas'r's parlor, displayed a white and brilliant set of teeth. Her woolly hair was braided in sundry little tails, which stuck out in every direction. The expression of her face was an odd mixture of shrewdness and cunning, over which was oddly drawn, like a veil, an expression of the most doleful gravity and solemnity. She was dressed in a single filthy, ragged garment, made of bagging; and stood with her hands demurely folded in front of her. Altogether, there was something odd and goblin-like about her appearance -- something as Miss Ophelia afterwards said, "so heathenish..."
by Tom Winston April 4, 2005
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Once a term of affection by a black mother for a black child, the word pickaninny is now considered a racist slur. Pickaninny is in actuality a contraction of "Pick a ninny" with "ninny" also being a contraction of the word "Nincompoop"
While watching thier children playing with some other kids, one black mother asked another "Who is the father of that child?". The other replied "Pickaninny" (Pick a ninny).
by WordSmith1965 December 11, 2012
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If you know what a honkey whisperer is and you know what a Pickaninny is? This has "what you talkin bout Willis" all over it!

A Honkey Whispering Pickaninny is a small version of a a Honkey Whisperer!
Emmanuelle Louis was the best Honkey Whispering Pickaninny that ever graced a camera!
by Sean Day Lou Swahili Swag September 3, 2016
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