Thanks to Russ and Gary's website for much of this information: "Writing of "My Boy Lollipop" is veiled in controversy. By most accounts, "My Girl Lollypop" was written by Bobby Spencer of the doo-wop group The Cadillacs with the group's manager Johnny Roberts getting co-writer credit. It was Spencer's misfortune to come into contact with the notorious record executive and music pubisher Morris Levy, who agreed to purchase the song from Spencer. Although not involved in the writing of the song, Morris Levy and alleged gangster Johnny Roberts listed themselves as the song's authors, to avoid sharing any royalties with it's original writer, Bobby Spencer. Levy removed Spencer's name from the original writing credits. He even claimed that "Robert Spencer" was a pseudonum. The Cadillacs' Spencer was later reinstated on the credits which unfortunately still lists Levy as a co-writer."

School girl Barbie Gaye was enlisted to record the song in 1956 and had to cut classes to record "My Boy Lollipop". With the help of radio personality Alan Freed, Barbie's recording was popular in New York City and a few other North Eastern cities. Like many other artists in her day, Gaye received no royalties from radio air play. Because her manager, Morris Levy's partner Corky Vastola, routinely counterfeited his artists music to keep all the profits, the record sales data is hard to determine.

Eight years later the song was discovered by Island Records founder Chris Blackwell who was trying to find songs for his young artist Millicent Smith of Jamaica. Her name was change to Millie Small and a top ten world-wide hit was born.