Jamaican teenager Millie Small stunned the music business by reaching number two in the U.S. and number one in the U.K. with "My Boy Lollipop" in 1964. Born Millicent Small in Clarendon, she was the daughter of an overseer on a sugar plantation (her reported date of birth varies from 1942 to 1948), and she was one of the very few female singers in the early Ska era in Clarendon. She was already recording in her teens for Sir Coxone Dodd's Studio One label with Roy Panton (as Roy & Millie), with a hit behind her in that capacity ("We'll Meet"), when Chris Blackwell discovered her and brought her to England in late 1963. Her fourth recording, "My Boy Lollipop," cut in London by a group of session musicians that included guitarist Ernest Ranglin (and, according to some accounts, Rod Stewart on harmonica) and featuring her childlike, extremely high-pitched vocals, was the first (and indeed, one of the few) international ska hits. It remains one of the biggest-selling reggae or ska discs of all time with more than seven million sales.
Millie, who was known as "the Blue Beat Girl" on her album, was perceived as a one-shot novelty artist from the start because of her unusual, almost screeching vocals (which actually owed a lot to Shirley Goodman of the '50s New Orleans R&B duo Shirley & Lee), and she only made the Top 40 one more time, with the "My Boy Lollipop" soundalike "Sweet William." She did cut an entire album around the two hits (and video clips exist of Millie miming to "My Boy Lollipop" and another single, "Henry"), which also includes the first of several of her covers of Fats Domino material ("I'm in Love Again") with whom she later recorded an entire album.
"My Boy Lollipop" (originally as My Boy Lollypop) is a song written in the mid-1950s and usually credited to the doo-wop group The Cadillacs's Robert Spencer, and to record company executive Morris Levy and Johnny Roberts. Robert Spencer's name was later removed from the original writing credits and replaced by that of the Morris Levy, who apparently claimed that Spencer's name had been his pseudonym.
The song was recorded first by Barbie Gaye as a minor Rhythm & Blues hit in 1956, but international recognition came with the Millie Small version in 1964. The song has been covered by many other artists.
The song was originally recorded by then 15-year old American singer Barbie Gaye and became a minor Rhythm & Blues hit in late 1956, spelled "My Boy Lollypop" (with a "y" not an "i") on the original 78 record label. Her version, with a similar rhythm to the later Millie Small recording, was a minor hit played on radio by Alan Freed, and she appeared in Freed's annual Christmas show at the New York Paramount in 1956. She also inspired singer/songwriter Ellie Greenwich to issue her first record as "Ellie Gaye".
It is most famous, however, for the 1964 recording by Jamaican singer Millie Small which is considered the first international ska hit.
The song was "discovered" by Chris Blackwell, who was trying to find songs for Millie Small to record. Millie's version was recorded in a ska/bluebeat-style, and in 1964 it became her breakthrough blockbuster hit in the United Kingdom, reaching #2. However they changed the spelling to read "lollipop" instead of "lollypop". The song also went to #1 in Republic of Ireland and #2 in the United States (on the Smash Record label).
"My Boy Lollipop" was the first record to help Blackwell's Jamaican label, Island Records, make millions. With over seven million copies sold, it remains one of the best-selling reggae/ska hits.
The record's arrangement is credited to Ernest Ranglin, who also plays guitar on the recording. A persistent rumor claims the not yet famous Rod Stewart performed the harmonica solo on the recording; Contrary to legend, the harmonica player was not Rod Stewart but Jimmy Powell of The Five Dimensions (previously a member of The Rockin' Berries). Powell personally asserts that it was he, not fellow Five Dimensions member Pete Hogman, who played this solo, contrary to many citations. ~SOURCES: Richie Unterberger & Bruce Eder, All Music Guide and Wikipedia
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