"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.
The original song, "My Girl Lollypop", was written by Robert Spencer of the doo-wop group The Cadillacs. Notorious record company executive Morris Levy agreed to purchase the song from Spencer. Although not involved in writing the song, Levy and alleged gangster Johnny Roberts listed themselves as the song's authors. In an effort to avoid sharing any royalties with Spencer, Levy removed Spencer's name from the original writing credits. Levy even claimed that Robert Spencer was his pseudonym.
The song caught the attention of one of Levy's partners, alleged mobster and music mogul Gaetano Vastola, aka "Corky". Vastola had recently discovered 14-year-old singer Barbie Gaye after hearing her sing on a street corner in Coney Island, Brooklyn. Vastola was so impressed that he immediately took her to meet New York radio DJ Alan Freed. Gaye sang a few songs for them and Freed was equally impressed. Vastola became Barbie Gaye's manager and within days, he acquired the sheet music and lyrics for "My Girl Lollypop" from Levy. He gave them to Gaye, with no specific instructions except to change the gender of the songs subject and be ready to perform it by the following week. Barbie Gaye changed the song's title to "My Boy Lollypop" and rewrote the song accordingly. She added non-lyrical sounds, (utterances), such as "whoa" and "uh oh," chose the notes for the lyrics, shortened and lengthened notes, decided which lyrics to repeat ("I love ya, I love ya, I love ya so") and added the word, "dandy" to describe to subject.
My Boy Lollipop was the first album for Millie and her only album for Smash Records. On the front and back of the album, Millie is called "the Blue Beat Girl." Ernest Ranglin was credited for the accompanyment and direction.
The back of the album contains an essay about Millie. It tells a little bit of her early life in Jamaica then tells how a talent contest led to a recording career and hit singles in Jamaica, which led to her discovery by British record producer Chris Blackwell. According to the essay, Blackwell then brought her to London to promote her talent and a new type of Jamaican music called "Ska." The essay also mistakenly says that she was born on October 8, 1948; she was actually born on October 6, 1946. The essay also includes quotes by Millie about her newfound fame. The essay's conclusion tells of the success of her hit "My Boy Lollipop" in the US and how it made her one of the most sought-after performers by producers of television and stage, and adds that Millie had also finished a movie role.