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Terry was a graduate at the Duke Ellington School of the Arts in Washington. He landed backing vocalist jobs for the R&B/pop group, Sweet Sensation, and hip-hop group The Boogie Boys. In 1987, he signed a recording contract with Epic/CBS Records. Terry's first single, "She's Fly", was released the same year, and peaked at number 10 on the Billboard R&B singles chart. Forever Yours, Terry's debut album for Epic, was released in 1988, and reached the Top 40 of Billboard's R&B albums chart. The follow-up single, "Lovey Dovey", reached number four on the R&B charts, and "Forever Yours" climbed into the R&B Top 20.
Terry's second album, a self-titled release, included the single "With You" (his biggest hit) which reached the Top 20 of the U.S. Billboard Hot 100, as well as the Top 10 on the R&B chart. "Everlasting Love", was a number-six R&B hit
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