Hines began his career by performing around the country as an act with his brother Maurice Hines. The two made their Broadway debuts in 1954's The Girl in Pink Tights, a musical starring Charles Goldner and French ballerina Zizi Jeanmaire.
In 1978, the Hines Brothers returned to Broadway in Eubie!, a musical revue celebrating composer Eubie Blake, who opened doors for the African-American theatre community with the success of his 1921 revue Shuffle Along.
Eubie! opened Sept. 20, 1978, at the Ambassador Theatre. Audiences responded enthusiastically with standing ovations, and the New York Times' Walter Kerr noted that "no one today taps faster than the Hines Brothers, who stopped the show a couple of times." Gregory received a Tony Award nomination for Best Featured Actor in a Musical.
His next Broadway role was in Comin' Uptown, an updated musical version of Charles Dickens' A Christmas Carol. In this version of the classic tale, Scrooge is a contemporary Harlem slumlord. Hines starred as Scrooge in a cast that included Tiger Haynes, Larry Marshall, Jenifer Lewis and Loretta Devine.
The musical opened Dec. 20, 1979, at the Winter Garden Theatre, where it ran for 45 performances. Though the show was panned by critics — the New York Times' Walter Kerr called it "careless and costly, elaborate and enervating" — Hines was Tony-nominated for his performance.
In 1981 Hines appeared in Sophisticated Ladies, a revue based on the music of Duke Ellington. Featured in the cast were Phyllis Hyman, P.J. Benjamin, Hinton Battle and Alvin Ailey dancer Judith Jamison.
The production opened March 1, 1981, at the Lunt-Fontanne Theatre and was well-received by critics. In his review for the New York Times, Frank Rich claimed Hines was "more than a dancer; he's the frisky Ellington spirit incarnate" and likened his tap-dancing abilities to "human lightning."
Sophisticated Ladies was nominated for eight Tony Awards, including Best Actor in a Musical for Hines, and went on to play 767 performances.
Hines made his final Broadway appearance in Jelly's Last Jam, based on the life and music of jazz musician Jelly Roll Morton. George C. Wolfe wrote the book and directed a cast that included Savion Glover, Keith David, Stanley Wayne Mathis and Tonya Pinkins. Hines starred as the title character and also created tap choreography for the show.
Opening night was April 26, 1992, at the Virginia (now August Wilson) Theatre. Frank Rich gave the show a rave review and praised Hines' performance: "Few, if any, tap dancers in this world can match him for elegance, speed, grace and musicianship, and, as if that weren't enough, he also happens to be a silken jazz crooner, supple in voice and plaintive in emotions."
The production ran for 569 performances and was nominated for an impressive 11 Tony Awards. Hines was nominated for both his performance and choreography, and he took home the 1992 Tony for Best Actor in a Musical.