Millie Small – My Boy Lollipop (1964) Millie Small 1964 My boy lollipop Did you know that... “My Boy Lollipop” was the first international hit based on the genre ska, which is a mix of R&B, jazz, and Caribbean music. It’s characterized by a “walking bass line” and an “off-beat” rhythm. How does this song make you feel? Report abuse SHARE THIS WITH YOUR FRIENDS