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In 1957 Morgan entered the Vere Johns Opportunity Hour, a talent show held at the Palace Theatre in Kingston. He won with rousing impressions of Little Richard and, shortly after that, was recruited to perform around the island with the popular Jamaican comedy team Bim and Bam. In 1959 Morgan entered the recording studio for the first time. Duke Reid, the acclaimed sound system boss, was looking for talent to record for his Treasure Isle record label. Morgan cut two popular shuffle-boogie sides "Lover Boy", a.k.a. "S-Corner Rock", and "Oh My". Soon after, Morgan cut the bolero-tinged boogie "Fat Man", which also became a hit. He also found time to record for Coxsone Dodd.
In 1960 Morgan became the only artist ever to fill the places from one to seven on the Jamaican pop chart simultaneously. Among those hits were "Don't Call Me Daddy", "In My Heart", "Be Still", and "Meekly Wait and Murmur Not". But it was the following year that Morgan released the biggest hit of his career, the Leslie Kong production of "Don't You Know", later retitled "Housewives' Choice" by a local DJ. The song featured a bouncing ska riddim, along with a duet by Morgan and Millicent "Patsy" Todd.
"Housewives' Choice" began the legendary rivalry between Morgan and Prince Buster, who accused Morgan of stealing his ideas. Buster quickly released "Blackhead Chiney Man", chiding Morgan with the sarcastic put-down, "I did not know your parents were from Hong Kong" – a swipe at Kong. Morgan returned with the classic "Blazing Fire", in which he warns Buster to "Live and let others live, and your days will be much longer.