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Gray joined The Roots in 1994 immediately after graduating from high school in Philadelphia. He replaced keyboard player Scott Storch joining the band in London. His first album with The Roots was Illadelph Halflife in 1996, and he has played on twelve of their fourteen studio albums.
Music writers have discussed Gray's background in classical and jazz piano with influences including Herbie Hancock and Thelonious Monk.[5] Critics have also discussed Gray's ability to integrate complex jazz styles into hip-hop keyboard rhythms, which has helped set the band apart from other hip-hop acts.[5]