Al Jolson (1886-1950) is best known as the star of Hollywood’s first sound feature film, The Jazz Singer. In his time, however, he left a much larger imprint. Born Asa Yoelson in Lithuania, he left for America in 1891 when his family relocated so that his father could earn a better living as a rabbi and cantor. He started performing in blackface in 1904 and continued to do so throughout his career, and while his relationship with African-American entertainers was more complex than that fact would indicate, he nevertheless remains the most famous face of a racist tradition in American entertainment. His prolific music and film career and his energy and charm got him nicknamed “The World’s Greatest Entertainer” during his life. Many of his performances would not pass muster today, and his legacy is a complicated one.