He began his career performing on Broadway musicals Hair and Via Galactica, before making his feature film debut appearing in Truck Turner (1974).
Shaw later appeared in films such as The Bingo Long Traveling All-Stars & Motor Kings (1976), Rocky (1976), The Boys in Company C (1978), The Great Santini (1979), Runaway (1984), The Monster Squad (1987), Harlem Nights (1989), Fried Green Tomatoes (1991), Rising Sun (1993), Cutthroat Island (1995), Daylight (1996) and Snake Eyes (1998).
[citation needed] He made his big screen debut appearing in the blaxploitation films Truck Turner and TNT Jackson, both released in 1974.
In 1976, Shaw starred in the sports comedy film The Bingo Long Traveling All-Stars & Motor Kings as Joseph Vanderbilt "Esquire Joe" Calloway alongside Billy Dee Williams, James Earl Jones and Richard Pryor.
[11] In 1986 he co-starred opposite Cicely Tyson and Martin Sheen in the made-for-television movie Samaritan: The Mitch Snyder Story and in 1987 starred in the controversial miniseries Billionaire Boys Club.
He also made appearances in television series Hill Street Blues, Fame, The Young Riders, Wiseguy and Murder, She Wrote.
He had a role in the 1995 comedy film Houseguest, alongside Sinbad, and appeared as a pirate in Cutthroat Island (1995) with Geena Davis.
In 2000s and early 2010s, Shaw left the screen, making only selected appearances in television series The X Files and CSI: Crime Scene Investigation.