At the age of six, Robinson began dancing for a living, appearing as a "hoofer" or song-and-dance man in local beer gardens. He soon dropped out of school to pursue dancing as a career. In 1886, he joined Mayme Remington's troupe in Washington, DC, and toured with them. In 1891, at the age of 12, he joined a travelling company in The South Before the War, and in 1905 worked with George Cooper as a vaudeville team. He gained great success as a nightclub and musical comedy performer, and during the next 25 years became one of the toasts of Broadway. Not until he was 50 did he dance for white audiences, having devoted his early career exclusively to appearances on the black theater circuit.