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Artists don't usually get much in the way of Royalties, those go to the Writers, in the case of "Lollipop" that was Robert Spencer.
@Cyber Liberty It was Robert Spencer---who wrote the song in 1956 while he was still a member of the Cadillacs. But . . . he had the misfortune of the song attracting the attention of the notorious Morris Levy, who agreed to be the song's publisher---then wiped Spencer's credit for writing the song and replaced it with that of a mobbed-up R&B artists' manager named Johnny Roberts while claiming that he, Levy, was really Robert Spencer.
Both Levy and the song, written originally as "My Girl Lollipop," caught the eye and ear of a mobster who was tight with Levy and had just discovered a Brooklyn girl named Barbie Gaye, Caetano (Corky) Vastola, an underboss in the notorious DeCavalcante crime family in New Jersey. Vastola, in turn, got the attention of DJ legend Alan Freed, then arranged for Gaye to cut the song on the Darl label. (Among the musicians on that record were two legendary New York studio rats, saxophonist Al Sears and drummer Panama Francis.) She cut it in the shuffle style then still new to R&B. Though it was hugely popular on Freed's radio show and around the northeast it didn't really catch elsewhere in the U.S.
Barbie Gaye was actually paid $200 flat for her record. It was more than Millie Small ever got for having the eventual (way) bigger hit, other than the big fees she collected for singing it on television appearances (including on the Beatles' early 1964 British special
Around the Beatles) around the world. British producer Chris Blackwell's re-discovery of the song on a reel-to-reel mix tape he'd acquired in 1964 led him to offer it to Small, a Jamaican teenager living in England whom Blackwell discovered, having her cut the song---not on his fledgling Island label in England, but leasing it to the Fontana label, and in the new ska style shuffle. The only thing keeping it from hitting number one in the U.S. in May 1964 was the Beach Boys' "I Get Around."
Barbie Gaye has another music history footnote: one of the kids who went for her original cut of "My Boy Lollipop" (spelled "Lollypop" on her record) was a Long Island girl named Ellie Greenwich, who adopted the stage name Ellie Gaye when she tried an early career as a recording artist before becoming the songwriting legend she eventually became.
This was Barbie Gaye's original recording . . .
Error 404 (Not Found)!!1. . . and this, of course, in all her make-Geddy-Lee-resemble-a-baritone glory, is Millie Small's international hit . . .
Error 404 (Not Found)!!1Millie Small's "My Boy Lollipop" has since sold over seven million copies on its own and remains one of the world's most popular early ska hits.