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.
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