Osborne was born in Providence, Rhode Island. He is the youngest of 12 children and is part of a musical family. He has five brothers and six sisters, some of whom went on to have music careers (his brother Billy was an L.T.D. bandmate). Osborne's father, Clarence "Legs" Osborne, was a popular trumpeter who played with Lionel Hampton, Count Basie, and Duke Ellington and died when Osborne was thirteen. Osborne started his music career in 1970 with a band called Love Men Ltd., who would later become known as L.T.D. The band recorded hit singles such as "(Every Time I Turn Around) Back in Love Again", "Concentrate on You," "Love Ballad" and "Holding On (When Love Is Gone)". At first, Osborne was a drummer, sharing lead vocal duties with his brother Billy, but by 1978 he became the group's primary lead vocalist. He and Billy both left L.T.D. in early 1980 to start solo careers. His solo success includes five gold and platinum albums.

In 1982, Osborne released his self-titled debut album, which featured two hit singles, "On the Wings of Love" and "I Really Don't Need No Light", peaking at #29 & #39 on the pop chart respectively. This was followed up the next year by Stay with Me Tonight, his first gold album (later reaching platinum album status), which spawned two more hits, "Don't You Get So Mad" (#25) and the title track (#30). "Stay with Me Tonight" (April 1984, #18) and "On the Wings of Love" (June 1984, #11) reached the UK Singles Chart.

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