1891, he was hired by Whallen and Martel, touring with Mayme Remington's troupe in a show titled The South Before the War, performing again as a pickaninny, despite his age. He travelled with the show for over a year before growing too mature to play the role credibly. In 1898, he returned to Richmond where he joined the United States Army as a rifleman when the Spanish–American War started. He received an accidental gunshot wound from a second lieutenant who was cleaning his gun. Vaudeville On March 30, 1900, Robinson entered a buck-and-wing dance contest at the Bijou Theatre in Brooklyn, New York, winning a gold medal and defeating Harry Swinton, star of the show In Old Kentucky and considered the best dancer of his day. The resulting publicity helped Robinson to get work in numerous travelling shows, sometimes in a troupe, more frequently with a partner, though not always as a dancer (Robinson also sang and performed two-man comedy routines). By 1912, Robinson was a full partner in the duo, which had become primarily a tap-dancing act, booked on both the Keith and Orpheum Circuits. The team broke up in 1914, and vaudeville performer Rae Samuels, who had performed in shows with Robinson, convinced him to meet with her manager (and husband), Marty Forkins. Under Forkins' tutelage, Robinson matured and began working as a solo act, increasing his earnings to an estimated $3,500 per week. Forkins accomplished this by inventing an alternate history for Robinson, promoting him as already being a solo act. This technique succeeded, making Robinson one of the first performers to break vaudeville's two-coloured rule, which forbade solo black acts. When the U.S. entered World War I, the War Department set up a series of Liberty Theatres in the training camps. The Keith Circuit and Orpheum Circuit underwrote vaudeville acts at reduced fees, but Robinson volunteered to perform gratis for thousands of troops, in both black and white units of the expeditionary forces, receiving a commendation from the War Department in 1918. Throughout the early 1920s, Robinson continued his career on the road as a solo vaudeville act, touring throughout the U.S. and most frequently visiting Chicago, where Marty Forkins, his manager, lived. From 1919 to 1923, he was fully booked on the Orpheum Circuit and was signed full-time by the Keith Circuit in 1924 and 1925. In addition to being booked for 50 to 52