Millie Small: "My Boy Lollipop" (1964) "My Boy Lollipop" (originally "My Girl Lollypop") is a song written in the mid-1950s by Robert Spencer of the doo-wop group The Cadillacs, and usually credited to Spencer, Morris Levy, and Johnny Roberts. It was first recorded in New York in 1956 by Barbie Gaye. A later version, recorded in 1964 by Jamaican teenager Millie Small, with very similar rhythm, became one of the top selling ska songs of all time. Eight years later the song was discovered by Islan