Hargrove spent one year (1988–1989) studying at Boston's Berklee College of Music but could more often be found in New York City jam sessions. He transferred to the New School in New York. His first recording there was with the saxophonist Bobby Watson. Shortly afterwards he made a recording with Superblue featuring Watson, Mulgrew Miller, Frank Lacy, and Kenny Washington. In 1990 he released his first solo album, Diamond in the Rough, on the Novus/RCA label. He was commissioned by the Lincoln Center Jazz Orchestra and wrote The Love Suite: In Mahogany which premiered in 1993.