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 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.In 1989, Tony was also featured in a duet with label mate Flame on the song "On The Strength", which reached number 59 on the Billboard R&B singles chart and number 11 on the Billboard Dance/Club Play chart.