[5] In 1978, Masterson was cast as Oscar Weinberg in the episode "Rosendahl and Gilda Stern Are Dead" on James Garner's NBC detective television series, The Rockford Files.
[8][9][10] In 1987, he played the character Couch in A Gathering of Old Men, the story of a group of elderly African-Americans who rally to the defense of a fellow black charged with the murder of a white tenant farmer.
[6] On October 23, 1989, he appeared as Dr. Nystrom in the television movie, False Witness, filmed in New Orleans, the story of a woman assistant district attorney who seeks to convict the killer of a controversial talk show hostess.
[10][11] In 1989, he was cast as a prison guard in the film The Outside Woman, starring Sharon Gless as a millworker who becomes a pen pal of a Louisiana State Penitentiary inmate, played by Scott Glenn.
[9][10][12] In 1994, he had a minor role as a reporter in the film, Blue Sky, with Tommy Lee Jones, Jessica Lange and Powers Boothe, a drama about 1950s weapons testing in the United States.