In the 1980s, Hines began landing roles that exploited both his dancing and dramatic abilities. His more notable feature credits include Francis Ford Coppola's "The Cotton Club" (1984), "White Nights" (1985), "Tap" (1989) and "A Rage in Harlem" (1991). For the most part, Hines was employed in these films as a debonair presence. He was more successful amidst the confusion of "The Cotton Club" than as an American communist within the anti-Soviet dullness of "White Nights". In the winningly cartoonish "A Rage in Harlem", Hines managed to inject lithe elegance into the thinly-scripted role of a 1950s criminal named Goldy.
Hines followed his award-winning Broadway success with "Renaissance Man" (1994), playing against type as an uncultured career Army officer opposite Danny De Vito's idealistic professor. That same year, he stepped behind the cameras to helm "Bleeding Hearts", an earnest look at an interracial romance that made the festival circuit. He subsequently appeared as Loretta Divine's love interest in "Waiting to Exhale" (1995) before tackling the nominal villain of "The Preacher's Wife" (1996), a real estate developer who wants to tear down the church and build condominiums. Hines had one of his best screen roles as a jazz musician afflicted with Tourette Syndrome in "The Tic Code" (1998). In 2000, he demonstrates his suaveness as Holly Hunter's married lover in the festival-screened "Things You Can Tell Just By Looking at Her" (aired on Showtime in 2001) but seemed miscast as a drug dealer's henchman in "Once in the Life".
While he had appeared in numerous variety specials and awards shows (picking up Emmy nods in 1982 and 1985), Hines had passed up many opportunities to topline his own TV series. Finally relenting, he agreed to star in the CBS sitcom "The Gregory Hines Show" (1997-98), in which he portrayed a widower struggling to raise a teenage son. The show, however, earned mixed reviews and struggled to find an audience. The performer fared somewhat better with his 1999-2000 recurring role on the highly-rated NBC sitcom "Will and Grace", as the lawyer boss of the former who had a brief romance with the latter. Also in 1999, Hines won a Daytime Emmy Award for his voice performance as Big Bill in Bill Cosby's animated TV series "Little Bill" (Nickolodeon, 1999-2002). Hines next had a starring role as a Spin magazine editor in the fact-based 2000 Showtime production "Who Killed Atlanta's Children?"
Fulfilling a dream, the dancer got to portray one of his idols in "Bojangles" (Showtime, 2001), a biopic of the great dancer Bill Robinson, for which he garnered a richly deserved Emmy nomination. Continuing his association with the network, Hines made his small screen directorial debut with "The Red Sneakers" (Showtime, 2001), a family drama about a high school student who is transformed by the titular footwear into a successful basketball player. Hines appeared as workaholic Mitch Rouse's best friend and boss in the short-lived TV series "Lost at Home" (ABC, 2003) and had future film roles scheduled until he succumbed to cancer at the early age of 57.