After four years in the military, he moved to Los Angeles, California, where he took acting lessons at the Pasadena Playhouse and dancing lessons in San Francisco in the early 1960s and worked as a transcript clerk at Los Angeles City College.[11] During this period, Freeman also lived in New York City, working as a dancer at the 1964 World's Fair, and in San Francisco, where he was a member of the Opera Ring musical theater group. He acted in a touring company version of The Royal Hunt of the Sun, and also appeared as an extra in the 1965 film The Pawnbroker. Freeman made his off-Broadway debut in 1967, opposite Viveca Lindfors in The Nigger Lovers[13][14] (about the Freedom Riders during the American Civil Rights Movement), before debuting on Broadway in 1968's all-black version of Hello, Dolly! which also starred Pearl Bailey and Cab Calloway.