If you are a fan of the 1950s, you know this song as “My Boy Lollypop” by Barbie Gaye was a big hit around the world in the summer of 1956. If you were a fan of bluebeat and ska, in 1964 you knew it was a ground breaker sung by Millie Small with its heavy Jamaican beat and a slightly different title spelling “Lollipop”.
Writing of this song in the mid 50s is veiled in controversy. By most accounts, “My Girl Lollypop” was written by Bobby Spencer of the doo wop band 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 publisher Morris Levy, who agreed to purchase the song from Spencer.
Sad news: Jamaican singer Millie Small has died May 5, 2020 at the age of 72 after suffering a stroke. Island Records founder Chris Blackwell announced her death and remembered her as “a sweet person… really special”.
Barbie Gaye – My Boy Lollypop / original version (with 5-note intro)
Millie Small – My Boy Lollipop
Doreen Shaffer & The Skatalites – My Boy Lollipop /ska version
Although not involved in writing the song, Morris Levy and alleged gangster Johnny Roberts listed themselves as the song’s authors, to avoid sharing any royalties with its original writer, Bobby Spencer.
Levy removed Spencer’s name from the original writing credits. He even claimed that “Robert Spencer” was his pseudonym. The Cadillacs’ Spencer was later reinstated on the credits which unfortunately still list Levy as a co-writer.
Robert Spencer was a prolific songwriter and a sometime member of various doo wop groups including The Crickets, The Crystals, The Harptones and The Cadillacs. The flipside of this record was written by Winfield Scott (one person), a.k.a. Robie Kirk, longtime member of The Cues who recorded under various names.
“My Boy Lollypop” was registered by Sylvia Music (owned by Al Sears who played sax on this record), 30 Oct 1956.
The Barbie Gaye version
The song caught the attention of one of Morris Levy’s partners, alleged mobster and music mogul Gaetano “Corky” Vastola. Vastola had recently discovered 14-year-old singer Barbie Gaye after hearing her sing on a New York street corner in Coney Island, Brooklyn. He was so impressed that he immediately took her to meet 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 also 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 the subject.
When it came time to record, Barbie cut school and took the subway to a recording studio in Midtown Manhattan. She 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 improvised music to match her vocals. They decided to record the song in a relatively new rhythm style of R&B called the shuffle. The shuffle sound was developed in the early 1940s in America’s black community and made popular by Professor Longhair, Rosco Gordon and Louis Jordan.
They recorded the song in one take. Barbie Gaye was paid $200 for her writing contributions to “My Boy Lollypop” and her studio recording.
Gaye’s recording was released as a single by Darl Records in late 1956. It was heavily played by Alan Freed, and listener requests made the song No. 25 on Freed’s Top 25 on New York radio station WINS 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 following year, Gaye toured with Little Richard and Fats Domino. The singer and songwriter Ellie Greenwich, (Be My Baby, Chapel of Love) then a teenager living on Long Island, was so taken by the record that she named herself Ellie Gaye when she embarked on her own recording career.
Barbie Gaye’s recording of “My Boy Lollypop” was popular in New York City, and a few other Northeastern cities. Like many artists in her day, Gaye received no royalties from radio play. Because her manager, Corky Vastola, routinely counterfeited his artists music to keep all the profits, the record’s sales data is difficult to determine.
Barbie’s voice brings to mind the styling and sound of her contemporary Brenda Lee. The B-side, “Say You Understand”, is a more typical R’n’B sound that showcases Barbie’s talents and re-enforces all comparisons to Brenda Lee.
Barbie Gaye would disappear into obscurity, but with an impact on the music scene through to the present day, as even the Spice Girls can be heard singing “My Boy Lollipop” in their film Spice World.
The Millie Small version
Fast forward to 1963.
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 Clarendon in Jamaica, who was under Blackwell’s supervision. Smith had been recording as a part of a duo called Roy and Millie for the Jamaican Studio One label, and managed to have a local hit with a song called “We’ll Meet”.
Blackwell arranged to have 16-year-old Millie Small flown from Kingston to London to manage her career. Millie’s shrill, joyful vocals, married to a galloping ska rhythm in Olympic Studios in London in an arrangement by the Jamaican master guitarist Ernest Ranglin, were beamed out all that summer from the new pirate radio stations, such as Radio Caroline, that were instrumental in helping promote the record. In May 1964, two months after the release of My Boy Lollipop, Millie was given a guest appearance on the ITV special Around the Beatles.
Changing the spelling to read “lollipop” instead of “lollypop”, Millie’s version was recorded in a similar shuffle/ska/bluebeat-style and the Island Records arrangement is credited to Ernest Ranglin, who also plays guitar on the recording. The saxophone solo from Barbie Gaye’s original R&B version was replaced by a harmonica solo.
In 1964 it became Millie’s breakthrough blockbuster hit in the UK, reaching No. 2. The song also went to No. 1 in Republic of Ireland, No. 2 in the USA, and No. 1 on the CHUM chart in Canada. With a monster sound built for AM radio, the track grabbed you and pulled you in.
It remains one of the biggest-selling ska songs of all time, with more than seven million sales.
Considered the first commercially successful international ska song, Small’s version of “My Boy Lollipop” sold over six million records worldwide and helped to put Island Records into mainstream popular music. It remains one of the best-selling reggae/ska hits of all time.
Cover versions and other uses
- Schlager singer Heidi Bachert recorded a cover version, under the same title but with German lyrics, which entered the West German Top 20 on August 15, 1964, remaining there for 17 weeks, with No. 5 as top position
- The song was remade in 1974 by Maggie Mae reaching No. 17 on the German chart.
- A cover version by Bad Manners, re-titled “My Girl Lollipop (My Boy Lollipop)”, was a UK Top 10 hit in July 1982.
- UK singer Lulu released a version of the song on the Jive label in 1986 and reached No. 86 in the UK singles chart; not high enough to be considered a hit in the official top 75.