He was playing in vaudeville shows by 1911, appearing in Irving Berlin's ragtime musicals. Harlan also played the role of Cap'n Andy in the first, part-talkie film version of  "Show Boat" (1929).
By 1911, Harlan had begun his career in live performances, starring in Irving Berlin's lively musical productions. He also played the part of Cap'n Andy in the initial silent film version of  "Show Boat" (1929), marking a significant milestone in his career.