Terry is a graduate at the Duke Ellington School of the Arts in Washington. He landed backing vocalist jobs for the freestyle/pop group Sweet Sensation, and hip-hop group The Boogie Boys.In 1987, he signed a recording contract with Epic/CBS Records. Terry's self-titled second album, released in 1990, included the single "With You" which reached the Top 20 of the U.S. Billboard Hot 100, as well as the Top 10 on the R&B chart.