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 teamBim and Bam. In 1959, Morgan entered the recording studio for the first time. Duke Reid, the 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 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. You said it. Now it's the Blazing Fire". Buster shot back with, "Watch It Blackhead", which Morgan countered with "No Raise No Praise" and "Still Insist". Followers of the two artists often clashed, and eventually the government had to step in with a staged photo shoot depicting the rivals as friends. Morgan had a major success in 1962 with "Forward March", a song celebrating Jamaican independence from Great Britain. In the mid-1960s, when ska evolved into rocksteady, Morgan continued to release top quality material, including the seminal rude boy songs, "Tougher Than Tough", "Do the Beng Beng", "Conquering Ruler", and a cover of Ben E. King's soul hit, "Seven Letters". Produced by Bunny Lee, "Seven Letters" is often cited as the first true reggae single. In 1969 Morgan recorded the skinhead anthem "Moon Hop". However, failing eyesight then forced him to give up regular stage appearances. Morgan still performs occasionally at ska revival shows across the world – often backed by the guitarist Lynn Taitt. He remained popular in Jamaica and the UK into the early 1970s, and has lived primarily in the UK or the US since the late 1960s. Morgan has written several songs that have won the Festival Song Contest for other artists, including "Jamaica Whoa", "Fi Wi Island A Boom", and "Progress". In July 2002 in Toronto, Ontario, Canada, a two-night "Legends of Ska" concert was held. Reuniting were The Skatalites, Lloyd Knibb, Rico Rodriguez, Lloyd Brevett, Lester Sterling, Johnny Moore and Lynn Taitt; along with Prince Buster, Alton Ellis, Owen Gray, Lord Creator, Justin Hinds, Derrick Harriott, Winston Samuels, Roy Wilson, Patsy Todd, Doreen Shaffer, Stranger Cole, Lord Tanamo and Derrick Morgan. In 2007 Morgan appeared on the bill at the annual Augustibuller music festival. His song "Tougher Than Tough" was featured in the video game . Morgan retired from the music industry because of illness in the 2010s, but returned in 2016 to collaborate with Kirk Diamond on a remake of Morgan's song 1960s "Conqueror". Morgan headlined the Supernova International Ska Festival, in Fredericksburg, Virginia on May 27–28, 2017.
