Douglas made his screen debut in 1971 in A Gunfight, starring his Father and Johnny Cash. In 1982, Douglas appeared in the NBC television film Remembrance of Love, also starring his Father. Douglas portrayed a younger version of his father's character in flashback scenes. He appeared in several films in the 1980s including The Flamingo Kid (1985), Tomboy (1985), The Golden Child (1986), and Honor Bound (1988). In the late 1980s, Douglas performed off-Broadway at the Village Gate Theater with the critically acclaimed improvisational comedy troupe Noo Yawk Tawk . He also appeared in a production of Dale Wasserman's Shakespeare and The Indians at the Music Theatre Conference for the Eugene O' Neill Theatre Center in 1981. Also in the production was folk performer Bobby Bridger, but the production never made it to Broadway.