In 1986, Boatman moved to Chicago, where he studied acting with Jane Brody, a popular acting teacher and casting director. Later that same year, he auditioned for and won the role of "Motown" in the critically acclaimed Vietnam action drama, "Hamburger Hill". That same year he appeared in "Running on Empty" with River Phoenix, and "The Trial of Bernard Goetz" for the PBS American Playhouse series. In 1988, he auditioned for the pilot episode of the Vietnam era television drama, "China Beach". He went on to play Samuel Beckett, the mortician in the China Beach mortuary, for the next three seasons. He later co-starred on "The Jackie Thomas Show" with Tom Arnold, and the short-lived WB series "Muscle". In 1996, he landed a role on the ABC sitcom, "Spin City", playing Carter Heywood, the irascible, openly gay minority affairs liaison. For his work on "Spin City" he was nominated for five NAACP Image Awards for Best Supporting Actor in a Comedy. He also won the GLAAD (Gay and Lesbian Association Against Defamation) award for Best Actor.