In 1967 Osbourne became the lead singer of The Wildcats and recorded for producer Winston Riley, even if nothing is done Wildcats' manager since financed a session at Coxsone Dodd's Studio One as his debut single "All I Have Is Love" was released In 1969 he recorded an album Come Back Darling again for Riley On the day when he finished album Osbourne moved to Toronto in Canada to be reunited with his family to sing with various soul and reggae groups, he became a singer for Ishan People and recorded two albums with their group disbanded in 1979 Osbourne and decided to return to Jamaica

Shortly after returning he recorded "Forgive Them" and "Jealousy Heartache And Pain" for the Studio One label, by late 1979 and early 1980, he recorded extensively for Dodd with These meetings conclude with truths and rights In 1979, he was also a hit for the king jammy (then Prince jammy) with "Folly Ranking" and an album of the same name followed in 1980 the success of these recordings made him one of meEach in-demand vocalists on the island and an abundance of material was also released Fally Lover Warrior Innah Disco Style and never stop fighting between 1980 and 1982 In 1983 he started the year with two big hits "Yo Yo" and "Lend me a helicopter and later during the year had continued success with "Water Pumping" an adaptation of Hopeton Lewis "Take It Easy" which also formed the basis for Johnny Clarke's 1976 hit "Rockers Time Now"

Number of hits continued with "Get Cracking" "Check For You "Rewind" (1984), "Buddy Bye" "No Sound Like We" and "field" (1985) In late 1980, he was particularly successful at recording for Bobby Digital, and had hits with "Good Time Rock '(1988) and "Rude Boy Skank" is (1988), both of which are included in his 1989 album tougher than them, as many as 80century, he continued to play for Coxsone Dodd and singles included "Keep That Light" "Unity" and "A We Run Things", but a long-awaited second album from Dodd has not materialized,