How Millie Small’s ‘My Boy Lollipop’ kickstarted reggae and ska (and apparently featured Rod Stewart)

The Jamaican singer, whose 1964 smash became an enduring pop favourite, has died at the age of 73. RIP

Millie Small, who has died at the age of 73, was still in her teens when she released the now-classic ‘My Boy Lollipop’ and paved the way for multiple Jamaican genres to take over on an international scale.

“It became a hit pretty much everywhere in the world,” her friend, Island Records founder Chris Blackwell, told the Jamaica Observer this week.  “I went with her around the world because each of the territories wanted her to turn up and do TV shows and such, and it was just incredible how she handled it. She was such a sweet person, really a sweet person.”

The first version of ‘My Boy Lollipop’, however, popped up around a decade before Small’s. The very first cut of the song was written by Robert Spencer of Harlem doo-wop group The Cadillacs – titled ‘My Girl Lollypop,’ it caught the attention of the notorious New Jersey music mogul and mobster Gaetano Vastola.

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Vastola quickly acquired the sheet music and lyrics, and took the song to a young artist named Barbie Gaye, whom he had overheard singing on a Brooklyn street-corner. Gaye gender-flipped the lyrics and cut the first recording of the track: the 1956 rhythm and blues version enjoyed heavy play around New York and soon made its way into the Jamacian sound-system scene after Island records’ Chris Blackwell began selling records to DJs in Kingston, Jamaica.

Eight years later, Blackwell was working with Millie Small to launch her career, and landed on ‘My Boy Lollypop’ as a potential second single – when he met her in England to discuss potential tracks, he dug up the original recording of the song on a reel-to-reel tape. Millie Small’s recording added a ska swagger to the 1956 version’s shuffle beat, and Island Records tinkered with the title spelling; Small’s distinctive, expressive vocals elevated it into a classic-in-waiting.

Released in 1964, ‘My Boy Lollipop’ bagged a number two single spot both in the UK and USA, and sold a whopping seven million singles worldwide: as well as boosting the profile of Island Records, it’s commonly regarded as the first ever international ska hit. To this day, it’s one of the biggest selling tracks from the genre.

Millie Smalls’ ‘My Boy Lollipop’ arrived at a relatively bleak time in history– the carefree hedonism of the Swinging Sixties was yet to unfurl, the Cold War was loitering ominously just around the corner and a full-blown economic crisis was unfolding in the UK.

Beatlemania had taken hold on both sides of the Atlantic and mods and rockers were scrapping for dominance, staging infamous showdowns in seaside towns and wreaking havoc on mopeds. As political dinosaurs ruled, youth subcultures were punching back against them. And  with her mischievously saccharine lyrics, unmistakable high-pitched vocal, punchy, off-beat rhythms and a freewheeling harmonica solo supposedly recorded by Rod Stewart (very much the stuff of urban legend), Millie Small was doing something completely and utterly different to the pack.

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Small become a star practically overnight and ‘My Boy Lollipop’ undoubtedly opened the doors for numerous genres that followed. Four years later, Toots and The Maytals coined the term “reggae” on ‘Do the Reggay’ (the word’s first usage in a song). Ska, reggae and two-tone all swept through the 1970s.

The singer would have one further Top 40 hi  with ‘Sweet William’ later that year, but she didn’t stick around for the ska takeover: by 1970 she’d quit the business altogether. Small maintained that she never received any royalties for ‘My Boy Lollipop’ and chose to stay out the public eye. “I’ve been happy living a quiet life,” she said in 2016, giving an incredibly rare interview, “sleeping and dreaming and meditating.”

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