In 1902 he joined forces with George W. Cooper. Bound by the "two colored" rule in vaudeville which restricted blacks to working in pairs, the two men worked the Keith and Orpheum circuits, eschewing the usual blackface makeup. Robinson was a gambler and in 1915, his hot temper and gold plated revolver got him arrested on an assault charge. That broke up his act and he began to work solo from that point on. Under the guidance of his manager, Marty Forkins, Robinson refined his act and began to make a name for himself in black nightclubs, earning up to $3,500 a week. In 1918 he introduced his famous Stair Dance, emitting a different pitch and rhythm with his feet on every stair. His dancing career was put on hold when he served as a rifleman with the Harlem Hellcats in France in WW1. He also served as the regiment's drum major.
Hailed as "The Dark Cloud of Joy" Robinson continued performing on the Orpheum circuit until he joined the cast of Blackbirds of 1928, a musical revue written by Dorothy Fields and Jimmy McHugh. He was 50 years old and it was the first time he would perform before a white audience. He starred with Adelaide Hall and introduced the song "Doin' the New Lowdown" and his Stair Dance. The two performers were an instant hit. The show ran for over a year and Robinson was proclaimed the greatest of all dancers by 7 New York newspapers. Brown Buddies in 1930 teamed Robinson and Hall again followed by Blackbirds of 1933, The Hot Mikado in 1939, All in Fun in 1940 and Memphis bound in 1945. He celebrated the opening of The Hot Mikado and his 61st birthday by dancing 61 blocks down Broadway.
As the appeal of black revues began to fade in the 30's Robinson made the leap to film, breaking the racial barrier. His first film in 1930, Dixiana, had a predominantly white cast but his next film, Harlem is Heaven in 1932, was the first all black film ever made. He would go on to make 14 films over the decade, remaining popular with white audiences but never breaking out of the nostalgic roles Hollywood cast him in. His series of films with Shirley Temple, Rebecca of Sunnybrook Farm, The Littlest Rebel, Just Around the Corner and The Little Colonel (where he was the first black man on film to dance with a white girl) had him playing the same stereotypical antebellum butler. Stormy Weather in 1943, loosely based on his own life, was the last film he made. Although he no longer made films or appeared on Broadway, he continued to perform in clubs well into his 60's.
Robinson was a dedicated member of Harlem's Hoofers Club, encouraging and inspiring many young dancers. Throughout his lifetime he was a member of many clubs and civic organizations and was an honorary member of police departments across the U.S. He was appointed an honorary Mayor of Harlem and was the mascot of the New York Giants baseball team. He co-founded the New York Black Yankees baseball team in 1936 which was a successful part of the Negro Leagues until it was disbanded in 1948 when Major League Baseball was desegregated. His participation in charities and benefits was legendary, giving away most of his fortune as gifts or loans. He died penniless of heart failure at the age of 71. His funeral was arranged by his long time friend, Ed Sullivan, and was attended by over 32,000 people.
Constance Valis Hill describes his tap style this way,"Onstage, his open face, twinkling eyes and infectious smile were irresistible, as was his tapping, which was delicate and clear. Buck or Time Steps were inserted with skating steps or crossover steps on the balls of the feet that looked like a jig, all while he chatted and joked with the audience. Robinson danced in split clog shoes, ordinary shoes with a wooden half-sole and raised wooden heel. The wooden sole was attached from the toe to the ball of the foot and left loose, which allowed for greater flexibility and tonality."
In his honor, May 25 has been declared National Tap Dance Day.
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