A life member of The Actors Studio,[1] Freeman appeared in a wide variety of plays, ranging from Leroi Jones' Slave/Toilet to Joe Papp's revivals of Long Day's Journey Into Night and Troilus and Cressida, and films, including My Sweet Charlie, Finian's Rainbow, and Malcolm X, as well as television series and soap operas, such as One Life to Live, The Cosby Show, Law & Order, Homicide: Life on the Street and The Edge of Night.

[2] Taking a hiatus from college, Freeman enlisted in the Air Force in 1951 to serve in the Korean War.

[3][4][5] He starred opposite Frank Sinatra in the 1968 Gordon Douglas film The Detective, before taking his most recognized acting role as police captain Ed Hall on the ABC soap opera One Life to Live from 1972 through 1987, with recurring appearances in 1988 and 2000.

His portrayal of Elijah Muhammad, the Nation of Islam leader, in the film Malcolm X earned him the 1992 NAACP Image Award for Outstanding Supporting Actor in a Motion Picture.

In the 1990s he had a recurring guest role as the manipulative Baltimore deputy police commissioner James Harris in Homicide: Life on the Street.