"My Boy Lollipop" (originally written as "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 cover version, recorded eight years later by Jamaican teenager Millie Small, with very similar rhythm, became one of the top selling ska songs of all time.

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 from the original writing credits, later claiming 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 legendary 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 and gave them to Gaye, with no specific instructions except to be ready to perform it by the following week. Barbie Gaye brought the music to her singing coach who played the song for her on piano a couple of times. Gaye changed the title to "My Boy Lollypop." She added and deleted lyrics (like, "uh oh lollipop" instead of "my boy lollipop" on a few instances), shortened and lengthened notes, repeated certain lyrics ("I love ya, I love ya, I love ya so") and added all the non-lyrical sounds, (utterances) such as the "whoas" and "hibbity-ops".
When it came time to record, Gaye cut school and took the subway to a recording studio in Midtown Manhattan. Gaye met the three members of the session band, guitarist, Leroy Kirkland, saxophonist, Al Sears and drummer, Panama Francis. The band leader, Kirkland, asked Gaye to sing the song for them. After listening to her, they changed parts of the original score to better match her vocal style. The generic rhythm & blues beat was replaced with a relatively new style becoming popularized by Jamaican musicians. The style was a mix of American jazz and R&B, with calypso and mento. The four artists went into the studio and recorded the song in one take. The combination of Barbie Gaye's energy and youthful vocals, the band's legendary talent, Kirkland's willingness to take a chance with such a new style, and the creative freedom they enjoyed to make all the changes they did, resulted in a song that would have great significance and would help to define the music genre known as ska.
The song was released as a single by Darl Records in late 1956. It was heavily played by New York radio DJ Alan Freed, and listener requests made the song #25 on Alan Freed's Top 25 on WINS, New York in November, 1956. The record sold in sufficient quantities locally to gain her a place in Freed's annual Christmas show at the New York Paramount in December 1956, when she opened for Little Richard. The singer and songwriter, Ellie Greenwich, then a teenager living on Long Island, was so taken by the record that she named herself Ellie Gaye when she embarked on her recording career. However, Gaye's recording of "My Boy Lollypop" failed to make an impression in other markets, and did not chart nationally. Consequently, the song remained obscure outside New York.