Bojangles' early life is obscured by legends, some of them propagated by himself, but it seems that he was orphaned as a baby (or at the age of six) and raised by his grandmother. He began to dance as a small child for pennies in the street, left school before he was eight, and ran away from home to Washington, DC, where he worked as a stable boy. He kept improving his dancing and in 1892 made he debut as a professional in The South Before the War, a minstrel show.
He went on to become a famous vaudeville and music theater star, noted as one of the first African-American entertainers to cross the racial divide in popularity with whites (his first appearance before a white audience was not until 1928), and the highest-paid Black entertainer in the world, although he attracted criticism for accepting stereotyped Black roles.
His 14 films included The Littlest Rebel and The Little Colonel, Rebecca of Sunnybrook Farm and Just Around the Corner, all with Shirley Temple, and his final film, Stormy Weather, with Lena Horne and an all-Black cast.
He was made honorary mayor of Harlem, and was famous for his lavish charity.