A famous talent agent, Nat Nazzaro, signed Green up as a client when he was just twelve years old.
Up until 1944, "Chuck and Chuckles" toured Europe, Australia, and the United States, performing in such venues as Radio City Music Hall, the Paramount, Apollo, and Capital theatres.
Jobs were plentiful and they would double up on performances, averaging five stage shows a day, playing nightclubs until early morning, and touring nonstop with big bands across the country and abroad.
He quickly adapted to bebop and created his own style of tap dancing, experimenting with new harmonies and rhythmic patterns.
In 1969, Green appeared with members of Harlem's Hoofers Club for a series of "Tap Happenings" that were produced in New York City by Letitia Jay.