Here’s today’s classic song of the day, “My Boy Lollipop.” You probably know it from the 1964 single by Jamaican singer Millie Small, which went to #2 on the Billboard Hot 100 and introduced ska music to the U.S. and the UK. Ms. Small’s version was not the original, however. That honor goes to a then-14 year-old singer named Barbie Gaye.
Barbie Gaye’s version of the song was recorded, under the name “My Boy Lollypop” (with a “y” instead of an “i”), in 1956. It was pushed hard by New York DJ Alan Freed and had some success on his radio station, WINS, reaching #25 on that station’s charts but going nowhere nationally. The feel is similar to Ms. Small’s later cover, with a similar ska-like beat, although it’s a little more like a blues shuffle with upbeat guitar hits. (Which is kind of what ska is, so the difference may be irrelevant).
Interestingly, Barbie Gaye’s recording featured only three musicians (Leroy Kirkland on guitar, Al Sears on sax, and Panama Francis on drums) and was done in a single take. Ms. Gaye received $200 for her efforts, which included rewriting the lyrics and rejigging the melody (more on that in a minute). She was a little white teenaged girl recording with three seasoned black R&B/jazz musicians, which was maybe a tad unusual back then, even in New York City.
A quick aside about the original song’s drummer, Panama Burke. He started out playing hot jazz and big band music in the 1930s, then in the 1950s made the transition into rhythm & blues and rock & roll. He played on a ton of hit records, including Wilson Pickett’s “In the Midnight Hour,” Sam Cooke’s “Twistin’ the Night Away,” Dion’s “Runaround Sue,” and Solomon Burke’s “If You Need Me.” He also played with Cab Calloway, Ray Conniff, Earl Hines, Dizzy Gillespie, Woody Herman, Lionel Hampton, and a lot more. This little gig was nothing more than a throwaway for him.
The song itself, under the title “My Girl Lollypop,” was written by Robert Spencer of the Cadillacs, a big doo-wop group in the 1950s. The writing is actually credited to Spencer, notorious record company executive Morris Levy, and alleged gangster Johnny Roberts. That, unfortunately, was a common practice back when the music business was slightly less scrupulous than it is today. (Only slightly; the mobsters seem not to be as involved these days.) One of Levy’s partners, Gaetano “Corky” Vastero (himself a soon-to-be convicted mobster), got a whiff of the tune and gave it to his protege Barbie Gaye, who he had discovered singing on a Coney Island street corner. He took the girl and the song to Alan Freed, who tasked her with changing the gender in the lyrics and then booked the recording session—and then promoted the heck out of it on his radio show. I’m sure no payola was involved.
Ms. Gaye did more than change “My Girl Lollypop” to “My Boy Lollypop.” She changed the melody all around, added all the nonsense vocal utterances, added the “you’re my sugar dandy” line, and just basically made it into something new. The rhythm arrangement, however, came from the musicians at the recording session, after listening to Ms. Gaye sing the song a cappella.
This was the only hit record for Barbie Gaye, real name Barbara Gaffney, who faded from the music scene fairly quickly. She toured with Fats Domino to support the release of “My Boy Lollypop” and released one more record (“Love Me a Little,” in 1961, which went exactly nowhere) but that’s about it.
“My Boy Lollypop,” however, made its way to Jamaica via Chris Blackwell, the founder of Island Records. He revamped it a bit and gave it to Millie Small, who recorded it in England early in 1964. That version is the one that hit big worldwide and the one you remember today. Barbie Gaye’s version is the oddity but well worth listening to—I find it fascinating how this obscure little R&B tune from a 14 year-old one-hit wonder helped to kick off the global ska music craze.
Back to Millie Small and today’s daily bonus video of the day. It’s Ms. Small performing a sped-up version of “My Boy Lollipop” (and two other tunes) live at the Sidney Myer Music Bowl in Melbourne, Australia, in 1965. Wow.
