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Millie Small - My Boy Lollipop Jamaican teenager Millie Small stunned the music business by reaching number two in the U.S. and number one in the U.K. with "My Boy Lollipop" in 1964. Born Millicent Small in Clarendon, she was the daughter of an overseer on a sugar plantation (her reported date of birth varies from 1942 to 1948), and she was one of the very few female singers in the early Ska era in Clarendon. She was already recording in her teens for Sir Coxone Dodd's Studio One label with Roy
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