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Theatrical “blackface” makeup used in vaudeville and minstrel shows assisted in the depiction of black characters in stereotypical ways. This tradition became popular in the mid-19th century in the United States. Arising from the tradition were popular stereotyped subcharacters that grew very popular; some examples are the darky, the coon, the mammy, the Uncle Tom, the buck, the Jezebel, and the pickaninny.

These stereotypical characters were exaggerated and two-dimensional. The darky, a simpleton and buffoon, was lazy and cowardly. The coon butchered the English language and put on airs trying to seem distinguished despite his obvious crude nature. The mammy, often played by men, was a sexually unappealing, stubborn, and bossy source of homespun “wisdom,” which was more likely to be more simple buffoonery and superstition. The Uncle Tom was a gentle, religious old man, sitting ineffectually on a porch, typically. Both the mammy and the Uncle Tom persist even in 2013 as logos for food products. The buck and the Jezebel were the threatening, hypersexualized male and female counterparts to the mammy and Uncle Tom or darky. Both the buck and the Jezebel were predatory and threatening to white culture. Finally, the pickaninny was the barefoot, ignorant black child.

From 1830 to 1930 the blackface performance was a key component of American theater. In the early 1900s blackface began to be performed apart from minstrel shows as its own independent kind of show. This phenomenon also thrived in the United Kingdom.

Blackface performers used burnt cork and later greasepaint and even shoe polish to achieve their exaggerated black skin. They used other makeup to accentuate their lips, and “nappy” wigs. The clothes of the blackface performer were generally shabby, ratty formal wear to further a ridiculous feel to the characters.

Al Jolson was a Jewish American actor, comedian, and singer. At the peak of his stardom he was known as the “World's Greatest Entertainer.” In the 1930s, he was America's most famous and highest-paid entertainer. Between 1911 and the end of the 1930s, Jolson performed in nine sold-out Winter Garden shows, made a series of successful musical films, traveled for 16 national and international tours, pressed in excess of 80 hit records, and in 1927 starred in the groundbreaking, first full-length movie with dialogue, The Jazz Singer.

Jolson's blackface and singing style are seen by experts as metaphors for the suffering of both Jews and blacks throughout history. Historian Michael Alexanderas calls The Jazz Singer a fictional blend of Jewish liturgical music and African American music in the form of jazz. The film, and Jolson specifically, were well received by Harlem audiences and critics alike.

The mid-20th century in the United States brought with it the civil rights movement and the end of blackface as a common theatrical form. The technique persists as of early 2013, typically as critical or satirical commentary, but also as political speech from across the spectrum. For example, some instances of blackface have been seen on the campuses of major southern universities such as the University of Alabama as recently as the early 1990s during Old South Week. One of the most enduring impacts of the blackface tradition was the ongoing co-opting of African American culture in the United States.

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