Blessed with a squeaky, high-pitched voice, Jamaican singer Millie Small was one of the pop sensations of 1964, thanks to her breakout hit single, “My Boy Lollipop,” which peaked at No. 2 in both the UK pop and US R&B charts. The record reportedly sold seven million copies worldwide, instantly transforming the teenager into an international star. Three years later, the iconic track appeared as the centerpiece of the singer’s first retrospective, The Best Of Millie Small.
The insanely catchy “My Boy Lollipop” represented a seismic moment in pop music history, when Jamaican ska music – an uptempo precursor to reggae – entered the mainstream and appeared on the radar of the wider public consciousness. The record’s phenomenal success brought the 16-year-old singer into the orbit of The Beatles, whose 1964 TV special Around The Beatles she appeared on. Her celebrity also put her on the iconic UK music show Ready, Steady, Go! and propelled her into the cast of a British television musical, The Rise & Fall Of Nellie Brown, which aired the same year. Such was her fame in the UK that she even cut a ska record called “The Bournvita Song,” promoting a hot beverage for chocolate manufacturer Cadbury’s.
The Best Of Millie Small is available on vinyl via the Black Story initiative. Order it now.
But matching “My Boy Lolipop’s” success was another matter. A follow-up single, “Sweet William” – cast from a similar stylistic ska-style mold – stalled at No. 30 in the UK chart while her debut album, More Millie (re-titled My Boy Lollipop for the US market) surprisingly failed to make any impression on the British albums chart. Millie scored one final British hit in 1965 – “Bloodshot,” a high-energy pop number that scraped into the UK Top 50 – before fading into obscurity. In 1967, however, Island Records attempted to revive her career with the fourteen-track The Best Of Millie Small, which perfectly summed up the Jamaican singer’s ebullient singing style.
Born Millicent Dolly May in Jamaica in 1947, Millie was the youngest of twelve children, raised in a shack on a sugar plantation where her father was a supervisor. A keen singer from an early age, at the age of 12, she won a radio station-sponsored talent contest held in Montego Bay’s Palladium Theatre. As a teenager, she came to the attention of the noted Jamaican record producer Coxsone Dodd, who gave her the stage name Millie Small. He signed her to his Kingston-based Studio One label, where she first tasted success in 1961 opposite singer Owen Gray on the duet “Sugar Plum,” a popular Jamaican hit. Another duet, 1962’s “We’ll Meet,” where she teamed up with Roy Panton, caught the ear of Chris Blackwell, a British music entrepreneur raised in Jamaica who had founded Island Records in 1959, an independent label that he used as a conduit to bring Caribbean music to the UK.
On hearing Small’s unique voice, Blackwell was instantly captivated. “There was no one who sang like Millie, with such wonderful little-girl earnestness,” he wrote in his biography The Islander: My Life in Music and Beyond. He persuaded Dodd to let him manage the singer, then 15, and got permission from her parents to take her to England. Blackwell was convinced he could transform her into a star, stating: “Of all the singers in Jamaica, Millie was the one I thought had the greatest chance of success in the UK.”
Blackwell became her legal guardian and enrolled his young charge at a London drama school, which he hoped would soften her rough edges and make her more palatable for UK audiences, though he emphasized, “I wasn’t trying to whiten Millie … though her impish Kingston patois needed a bit of massaging.”
The first single he made with her, “Don’t You Know,” a driving slice of teen R&B released by the Fontana label, was a flop, but then Blackwell found what he believed was the perfect song for her, “My Boy Lollipop,” which was an old US R&B track first recorded by teenage singer Barbie Gaye in 1956. Using the eminent Jamaican guitarist Ernest Ranglin as his arranger, he gave the tune a ska makeover, a fresh, new, and infectious sound that was tailor-made for huge chart success.
The timeless track was the undoubted focal point of The Best Of Millie Small, which included Millie’s two other UK hit singles “Sweet William” and “Bloodshot Eyes.” Her brilliance as a ska pioneer was also reflected in the catchy self-written “Oh Henry,” taken from Small’s debut album More Millie, and “Wings Of A Dove,” the B-side to the 1967 pop-meets-vaudeville-style single, “Chicken Feed,” which was also included.
The Best Of Millie Small also revealed that there was much more to the so-called “Blue Beat Girl” than “My Boy Lollipop.” The non-album single “Killer Joe” put her in an R&B setting, while its B-side “Carry, Go, Bring Home” sounded like calypso-tinged beat pop. There was also an aching rendition of soul man Sam Cooke’s bluesy ballad “Bring It On Home To Me,” released as a single B-side. Later, there’s the bluesy “Three Nights A Week” and “Walkin’ To New Orleans,” both plucked from the singer’s second, largely forgotten album, Millie Sings Fats Domino, a tribute to the New Orleans singer who was hugely popular in Jamaica. Small’s voice was framed on those two tracks by thick orchestral strings over chugging R&B backbeats.
Despite the popularity of “My Boy Lollipop” – which would be covered by everyone from Teresa Brewer to Bad Manners over the years – The Best Of Millie Small didn’t sell enough copies to break into the UK and US charts. Today, however, it offers a vivid reminder of the girl from Clarendon, Jamaica, who took the world by storm in 1964 and put ska music on the international music map.
The Best Of Millie Small is available on vinyl via the Black Story initiative. Order it now.
