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"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.

The Barbie Gaye versionEdit

"My Boy Lollypop"
Single by Barbie Gaye
B-side "Say You Understand"
Released 1956
Genre Rhythm & Bluesska
Length 2:18
Label Darl
Writer(s) Robert Spencer, Morris Levy, Johnny Roberts
Producer Leroy Kirkland, Barbie Gaye

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 IslandBrooklyn. 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. It was arranged in shuffle style, a popular beat in the black community, as previously recorded in New Orleans by Professor Longhair, in Memphis by Rosco Gordon and more famously by Louis Jordan and the Tympany Five, who had scored several hits using this rhythm since at least 1942 (including the 1944 number one R&B hit G.I. Jive). The shuffle beat was also popular on Jamaican dance halls. The four artists, featuring the white teenage girl, went into the studio and recorded the song in one take.

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 No. 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.

The Millie Small versionEdit

"My Boy Lollipop"
Single by Millie Small
from the album My Boy Lollipop
B-side "Something's Gotta Be Done"
Released 1964
Genre Pop, Ska
Length 2:01
Label FontanaIslandSmash
Writer(s) Morris Levy, Johnny Roberts
Producer Chris Blackwell

Eight years later the song was discovered by Island Records founder, Chris Blackwell, who was trying to find songs for his young artist, Millie Small, to record. Changing the spelling to read "lollipop" instead of "lollypop", Millie's version was recorded in a similar shuffle/ska/bluebeat-style, and in 1964 it became her breakthrough blockbuster hit in the United Kingdom, reaching #2. The song also went to No. 1 in Republic of Ireland and No. 2 in the United States (on the Smash Record label). Considered the first commercially successful international ska song, Small's version of "My Boy Lollipop" sold over six million records worldwide and helped to launch Island Records into mainstream popular music. It remains one of the best-selling reggae/ska hits of all time.

The record's arrangement is credited to Ernest Ranglin, who also plays guitar on the recording. The saxophone solo from the original version was replaced by a harmonica solo. It is unclear who played the harmonica – urban legend credited Rod Stewart for many years, but he has denied it. Instead, it was almost certainly either Pete Hogman or Jimmy Powell, both of The Five Dimensions. Pete Hogman and Five Dimensions guitarist Kenny White both maintain it was Pete Hogman, while Jimmy Powell asserts that it was he who played this solo.

British reggae DJ David Rodigan has stated that watching Millie Small perform the song at the Ready Steady Go! TV show as a school boy initiated his lifelong passion for Jamaican music.The song featured in the 2012 Summer Olympics opening ceremony in London.

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