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Pickaninny (also picaninny, piccaninny or pickinniny) is a term in English which refers to a racist and derogatory caricature of dark-skinned children of African descent. It is a pidgin word form, which may be derived from the Portuguese pequenino (a diminutive version of the word pequeno, "little"). In modern sensibility, the term implies a caricature which can be used in a derogatory and racist sense. According to the scholar Robin Bernstein, who describes the meaning in the context of the United States, the pickaninny is characterized by three qualities: "the figure is always juvenile, always of color, and always resistant if not immune to pain". These three qualifiers demonstrate the dehumanizing nature of the pickaninny caricature and are reflective of the predominantly colonial society in which its use was popularised, where Portuguese values predominated. 
Although the Oxford English Dictionary quotes an example from 1653 of the word "pickaninny" used to describe a child, it may also have been used in early African American vernacular to indicate anything small, not necessarily a child. In a column in The Times of 1788, allegedly reporting a legal case in Philadelphia, a slave is charged with dishonestly handling goods he knows to be stolen and which he describes as insignificant, "only a piccaninny cork-screw and piccaninny knife — one cost six-pence and tudda a shilling..." The anecdote goes on to make an anti-slavery moral however, when the black person challenges the whites for dishonestly handling stolen goods too - namely slaves - so it is perhaps more likely to be an invention than factual. The deliberate use of the word in this context however suggests it already had black vernacular associations. In 1826 an Englishman named Thomas Young was tried at the Old Bailey in London on a charge of enslaving and selling four Gabonese women known as "Nura, Piccaninni, Jumbo Jack and Prince Quarben".
In the Southern United States, pickaninny was long used to refer to the children of African slaves or (later) of dark-skinned African American citizens. While this use of the term was popularized in reference to the character of Topsy in the 1852 book Uncle Tom's Cabin, the term was used as early as 1831 in an anti-slavery tract "The History of Mary Prince, a West Indian Slave, related by herself" published in Edinburgh, Scotland. The term was still in some use in the United States as late as the 1960s.
In literature, films, and music
Many old lullabies have the word "pickaninny" in them — used as an affectionate term for babies — often interchangeable with a child's name, i.e.: to personalize the song many families have substituted the children's name. "It's time for little Pickaninnies to go to sleep."
Samuel Foote's 1755 nonsense prose includes: "there were present the Picninnies, and the Joblillies, and the Garyulies, and the grand Panjandrum himself...."
In the 1931 film, 'The Front Page', one of the reporters played by Frank McHugh, calls in a story to his newspaper about a colored woman giving birth to a pickaninny in the back of a cab. The term is used twice in the scene.
The original version of the 1914 lullaby "Hush-A-Bye, Ma Baby" (The Missouri Waltz) contains the line "when I was a Pickaninny on ma Mammy's knee." When it became the state song of Missouri in 1949, the word "pickaninny" was replaced with "little child." 
The term is used in the fourth verse of the Jimmie Rodgers tune "Peach Pickin' Time in Georgia". "When the picannies pick the cotton, I'll pick a wedding ring."
In Flannery O'Connor's "A Good Man Is Hard to Find", the grandmother uses the term: "'In my time,' said the grandmother, folding her thin veined fingers, 'children were more respectful of their native states and their parents and everything else. People did right then. Oh, look at the little pickaninny!' she said and pointed to a negro child standing in the door of a shack. 'wouldn't that make a picture.'"
Throughout his 1935 travel book Journey Without Maps, British author Graham Greene uses "piccaninny" as a general term for African children. In Margaret Mitchell's best-selling 1936 epic Gone with the Wind, Melanie Wilkes objects to her husband's intended move to New York City because it would mean that their son Beau would be educated alongside Yankees and pickaninnies. Orson Scott Card's historical fantasy series The Tales of Alvin Maker uses the term, such as in Seventh Son: "Papooses learnt to hunt, pickaninnies learnt to tote...."
In the 1935 Shirley Temple film The Littlest Rebel the word "pickaninny" is used to describe the young slave children who are friends to Virgie, but excluded from her birthday party at the beginning of the film.
In the 1936 film Poor Little Rich Girl, Shirley Temple sings the song "Oh, My Goodness" to four ethnically stereotyped dolls. The fourth doll, representing a black African woman or girl, is addressed as "pickaninny".
In the 1936 Hal Roach feature General Spanky starring the Our Gang children, Buckwheat gets his foot tangled in the cord that blows the whistle on the river boat. Buckwheat is untangled by the captain of the river boat who hands him over to his master and tells him to keep an eye on that little pickaninny.
In the 1940 film His Girl Friday, McCue, one of the press room reporters, jokes that "Mrs. Phoebe DeWolfe" gave birth to a pickaninny in a patrol wagon, concluding, "When the pickaninny was born, the Rifle Squad examined him carefully to see if it was Earl Williams. Well, they knew he was hiding somewhere."
In the opening line of Robert Wise's 1959 film Odds Against Tomorrow which tackled issues of racism, Robert Ryan's character picks up a young black girl after she bumps into him and says, "You little pickaninny, you're gonna kill yourself flying like that."
The Australian folk-rock band Redgum used the word in their song "Carrington Cabaret" dealing with white indifference to the problems of aboriginal Australia on their 1978 album If You Don't Fight You Lose.
The word was used by Australian country music performer Slim Dusty in the lyrics of his 1987 "nursery-rhyme-style" song "Boomerang": "Every picaninny knows, that's where the goes." Within Australia, it is also a common name used for landscape features, including Piccaninny crater, Picanniny Point and Piccaninnie Ponds Conservation Park.
The original first line of The Missouri Waltz was "Way Down in Missouri Where I Heard This Melody, When I was a Pickaninny on My Mammy's Knee." It has since been changed to "When I Was a Little Baby on my Mama's Knee."
The term was controversially used ("wide-grinning picaninnies") by the British Conservative politician Enoch Powell in his "Rivers of Blood" speech on 20 April 1968. In 1987, Governor Evan Mecham of Arizona defended the use of the word, claiming: "As I was a boy growing up, blacks themselves referred to their children as pickaninnies. That was never intended to be an ethnic slur to anybody." Before becoming the Mayor of London, Boris Johnson wrote that "the Queen has come to love the Commonwealth, partly because it supplies her with regular cheering crowds of flag-waving piccaninnies." He later apologised for the article. 
The word 'piccaninny' is used throughout the Pacific Melanesian countries as a catchall term to describe children in general.
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The term is in current use as a technical term in Chess Problems, for a particular set of moves by a black pawn.
Cognates of the term appear in other languages and cultures, presumably also derived from the Portuguese word, and it is not controversial or derogatory in these contexts. It is in widespread use in Melanesian pidgin and creole languages such as Tok Pisin of Papua New Guinea, as the word for "child" (or just young, as in the phrase pikinini pik, meaning piglet). Indeed, even in quite formal events, HRH Prince Charles is referred to using the term in Tok Pisin, and has delighted in describing himself, when using this language in speeches to native speakers, as, "nambawan pikinini blong Kwin" ("number-one pickaninny belong queen", i.e. The First Child of the Queen).
In certain dialects of Caribbean English, the words pickney and pickney-negger are used to refer to children. Also, in Nigerian as well as Cameroonian Pidgin English, the word pikin is used to mean a child. And in Sierra Leone Krio the term pikin refers to child or children, while in Liberian English the term pekin does likewise. In Chilapalapa, a pidgin language used in Southern Africa, the term used is pikanin. In Surinamese Sranan Tongo the term pikin may refer to children as well as to small or little. Some of these words may be more directly related to the Portuguese pequeno than to pequenino, the source of pickaninny.
- "pickaninny". Oxford English Dictionary online (draft revision ed.). March 2010.
Probably < a form in an (sic) Portuguese-based pidgin < Portuguese pequenino boy, child, use as noun of pequenino very small, tiny (14th cent.; earlier as pequeninno (13th cent.))...
- Room, Adrian (1986). A dictionary of true etymologies. London: Routledge and Kegan Paul Inc. p. 130.
- Bernstein, Robin (2011). Racial Innocence: Performing American Childhood from Slavery to Civil Rights. New York: New York University Press. p. 35.
- "JCM: The Picaninny Caricature". www.ferris.edu. Retrieved 2016-04-11.
- "pickaninny". Oxford English Dictionary online (draft revision ed.). March 2009.
1653 in N. & Q. (1905) 4th Ser. 10 129/1 Some women [in Barbados], whose pickaninnies are three yeares old, will, as they worke at weeding..suffer the hee Pickaninnie, to sit astride upon their backs.
- "Black and White, A Modern Anecdote", The Times, 22 August 1788; Issue 1148; p.4; col B.
- The Times, 25 October 1826; Issue 13100; p.3; col A, Admiralty Sessions, Old Bailey, Oct. 24.
- "National Museum of Australia - 'Last of the Tribe'". nma.gov.au.
- Meakens, Felicity (2014). Language contact varieties. p. 367. Retrieved 28 March 2016.
- "Past gaffes from Britain's new Foreign Secretary Boris Johnson". www.news.com.au. Retrieved 2016-07-21.
- Maiden, Siobhan. "The Picaninny Point Debacle". ABC Australia. Retrieved 31 July 2015.
- Watkins, Ronald J. (1990). High Crimes and Misdemeanors: The Term and Trials of Former Governor Evan Mecham. William Morrow & Co. p. 72. ISBN 978-0-688-09051-7.
- "Boris says sorry over 'blacks have lower IQs' article in the Spectator". Evening Standard. 2 April 2008. Retrieved 31 July 2015.
- Telegraph: Original article by Boris Johnson from 10 January 2002
- "Prince of Wales, 'nambawan pikinini', visits Papua New Guinea" in The Telegraph, 4 Nov 2012
- Faraclas, Nicholas G. Nigerian Pidgin. p. 45. N.p.: Routledge, 1996. ISBN 0-415-02291-6, p. 45, via Google Books.
- Cassidy, Frederic Gomes and Robert Brock Le Page. Dictionary of Jamaican English. p. 502. 2nd Edition. Barbados, Jamaica: University of the West Indies Press, 2002. ISBN 976-640-127-6. via Google Books
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