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After scoring with “My Boy Lollipop,” Island became a financially vibrant label able to promote reggae to the world. She’d been cutting records in since age 12, starting with the legendary Coxsone Dodd. His first signing was the pint-sized 16-year old Jamaican Millie Small. In 1959, Island Records formed around Blackwell’s love of Jamaican ska and bluebeat music-the precursors of reggae. Otherwise, Cliff and Marley might have kept on doing backwater knock-offs of American R’n’B.
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Their career breakthroughs, however, happened after Chris Blackwell signed them to Island Records and urged them to elevate reggae into a fresh, progressive style. There’s no doubt that Jimmy Cliff and Bob Marley are the lions of Jamaican music, outstanding singer-songwriters who championed reggae’s impact on mainstream culture. Related: “Sixty-Minute Man: He’ll Rock You and Roll You” Sadly, we lost her in May 2020, so it’s worth revisiting her career. In the USA she was tagged as a novelty, but in truth, she was a catalyst in a chain of events that changed the course of popular music. Singer-songwriter Millie Small is best known for her 1964 Top 10 hit “My Boy Lollipop,” the bouncy ear-candy that sold millions and made her the Caribbean’s first international pop star.