Terry landed backup singing jobs for the R&B/pop group Sweet Sensation and hip-hop group The Boogie Boys. In 1987, he signed a record deal with Epic/CBS Records. Terry's first single, "She's Fly", was released the same year, and peaked at number 10 on Billboard's R&B Singles chart. Forever Yours, Terry's debut album for Epic, was released in 1988, and reached the Top 30 of Billboard's R&B albums chart. The follow-up single, "Lovey Dovey", hit number-four on the R&B charts. The single Forever Yours reached 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 Twenty of the U.S. pop chart, as well as the Top Ten on the R&B chart. "Everlasting Love", a number-six R&B hit, was also successful on the R&B chart. After leaving Epic, Terry moved over to Virgin Records. His debut album for the label was 1994's Heart Of A Man. The single, "When A Man Cries", just managed the R&B Top 40, and the album was a commercial failure in terms of sales. The following year, Terry contributed background vocals on the single "Gotta Have Love", from Yolanda Adams's album More Than A Melody. He also appeared in the video. He has performed on the soundtracks to Gladiator starring Cuba Gooding, Jr., Tap starring Gregory Hines and King's Ransom starring Anthony Anderson. In 1991, Terry earned two “Soul Train Music Awards” nominations: Artist of the Year and Single of the Year for “With You” but did not win.
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