This week, we delve into the infectious rhythm of “My Boy Lollipop” by Millie Small, a song that not only topped charts worldwide but also served as a pivotal moment in the global emergence of ska music. This seemingly simple tune, often categorized as a novelty, holds within it the vibrant origins of a genre that would profoundly influence music for decades to come. Let’s explore the fascinating story behind this Lollipop Song and its crucial role in music history.
The narrative of rock music, as often told, predominantly features artists from America and Britain. While musical innovation flourishes globally, the Anglo-American axis has historically dominated the industry, sometimes overshadowing significant contributions from elsewhere. However, occasionally, a sound from beyond these borders breaks through, captivating audiences and leaving an indelible mark. “My Boy Lollipop” is one such record, a vibrant export from Jamaica that charmed the world.
To truly understand the impact of this lollipop song, we need to journey to the heart of Jamaica in the 1950s and early 60s. This era was characterized by stark economic disparity. While poverty was a reality in many communities that birthed early rock and roll in America and post-war Britain, Jamaica’s situation was unique. Access to even basic amenities like record players and radios was extremely limited for the majority of the population. Music, therefore, wasn’t a solitary pastime but a deeply communal experience.
A jukebox, with the words
Kingston, Jamaica, became the epicenter of this communal music scene, revolving around “sound systems.” These were essentially mobile discos – powerful public address systems set up by DJs who would play records for dancing in open-air spaces. Initially, these systems were used by shops to attract customers, but their popularity soon exploded, evolving into independent mobile parties. The music played at these sound systems differed drastically from the radio broadcasts, which catered to the wealthier, predominantly white British colonial class. A stark musical divide existed between the colonizers and the colonized.
The indigenous music of Jamaica at the time was primarily “mento.” Interestingly, “mento” itself encompasses diverse styles. Rural mento featured instruments like banjos and the “rhumba box,” a homemade bass, bearing sonic similarities to American country music and British skiffle. In Jamaica, this form was often simply called “country music.”
[Excerpt: The Hiltonaires, “Matilda”]
Urban mento, on the other hand, embraced instruments common in R&B and jazz bands, moving away from acoustic and homemade sounds. While sources differentiate urban mento from calypso, primarily associated with Trinidad and Tobago, the exact distinctions remain somewhat elusive. Mento musicians themselves sometimes used the term “calypso” to market their music to international audiences unfamiliar with the nuances. This explains why you might find mento groups with names like “Count Lasher and His Calypsonians” and songs titled “Hoola Hoop Calypso.”
[Excerpt: Lord Power and Trenton Spence, “Strip Tease”]
Mento was primarily a live performance genre in its early days. Recording facilities in Jamaica were scarce, and record production was limited, mainly catering to tourists seeking souvenirs. Sound systems initially played a mix of mento, Latin-flavored music, and, most importantly, American R&B by Black artists. Figures like Louis Jordan, Wynonie Harris, Fats Domino, and Lloyd Price were incredibly popular. Wynonie Harris’s “Bloodshot Eyes,” despite its disturbing lyrical content by modern standards, was a massive hit in the early sound system scene and significantly shaped Jamaican musical tastes.
[Excerpt: Wynonie Harris, “Bloodshot Eyes”]
These American records weren’t readily available in Jamaica. Merchant seamen played a crucial role, tasked by “sound men” (the DJs) to procure new and exciting records, often in exchange for rum or marijuana. Sound men were more than just DJs; they were performers who hyped up the crowd, invented dance moves, and manipulated sound with echo and boosted bass. A sound man’s prestige hinged on possessing exclusive records. To maintain exclusivity, they would scratch off labels and rename records, preventing rivals from copying them.
This quest for sonic supremacy fueled intense rivalry between sound men, initially friendly but escalating as figures like Duke Reid, a former policeman turned gangster, entered the scene with his Trojan sound system. Intimidation and even violence became part of the competition. Reid, who began as an R&B radio DJ, used Tab Smith’s “My Mother’s Eyes” as his theme song, forever associating the tune with his Trojan sound.
[Excerpt: Tab Smith, “My Mother’s Eyes”]
Reid’s Trojan and Coxsone Dodd’s Downbeat were the two giants of the Kingston sound system scene. Dodd’s Downbeat became so extensive that he operated five systems nightly across the city, managed by assistants who later became Jamaican music icons, such as Prince Buster and Lee “Scratch” Perry.
Prince Buster played a key role in helping Dodd stay ahead of the competition. Buster’s deep knowledge of R&B allowed him to identify records played by Duke Reid, even from just listening. He could discern production styles and lyrics to deduce song titles and labels. Dodd would then task merchant seamen to find these records in America, press copies locally, and distribute them to other sound men, undermining Reid’s exclusivity.
Eventually, Prince Buster established his own sound system, intensifying the rivalry. Dodd possessed superior technology, Buster was the ultimate showman, and Reid wielded influence and intimidation, but all three contributed to a vibrant and fiercely competitive scene. Sound system loyalty became deeply ingrained, akin to sports team or political allegiance, sometimes leading to violent clashes between rival supporters.
However, relying solely on American records presented challenges. As American musical tastes shifted towards Elvis, Jerry Lee Lewis, and Bobby Darin, Jamaican audiences still craved the sounds of Louis Jordan, Fats Domino, and Gene & Eunice. While sound men initially found obscure older R&B records, this supply was finite.
The solution was clear: Jamaica needed its own R&B. Fortuitously, Kingston hosted a weekly talent contest where winners received five pounds – a significant sum at the time. Many winners used their prize money to record themselves at disc-cutting services, creating single-copy records. These unique recordings could then be sold to sound men, guaranteeing exclusivity.
Initially, only smaller sound systems, lacking American connections, were interested in local recordings. However, these local tracks gained popularity, demonstrating their appeal. Larger systems began using smaller ones as test markets. If a local record resonated with a smaller system’s audience, a major operator would acquire it.
A prime example is “Lollipop Girl” by Derrick Harriott and Claudie Sang. Recorded with just piano backing, their single copy became a sensation on a smaller sound system. Coxsone Dodd traded an American record for it, and its success led Duke Reid to bribe Dodd’s assistant to obtain a copy for himself. During a sound clash between Dodd and Reid, when Reid played his version of “Lollipop Girl,” tensions escalated to the point where Dodd pulled a gun on Reid.
Recognizing the immense popularity of “Lollipop Girl,” Reid took matters into his own hands. He signed Harriott, assembled top local musicians, and recorded a full band version. He played it on his sound system and released it as a record.
[Excerpt: Derrick Harriott, “Lollipop Girl”]
While Reid didn’t produce many more records immediately, Coxsone Dodd and Prince Buster launched their own labels, nurturing local talent. A pool of talented session musicians, including trombonist Rico Rodriguez and guitarist Ernest Ranglin, became central to the burgeoning Jamaican recording industry.
From these recordings, a new genre emerged in the late 1950s: ska. Three records are considered pivotal in its development. The first was produced by Edward Seaga, later Prime Minister of Jamaica. Seaga subtly incorporated mento rhythms into an R&B track, “Manny Oh” by Higgs and Wilson. By stressing the off-beats – “one AND two AND three AND four AND” – instead of the usual on-beats, Seaga created a uniquely Jamaican feel, even if subtle to untrained ears.
[Excerpt: Higgs and Wilson, “Manny Oh”]
The second milestone, produced by Dodd, is often hailed as the first true ska record: “Easy Snappin'” by Theo Beckford. The term “ska” itself is rumored to have originated from Dodd instructing arranger Ernest Ranglin to “play it ska… ska… ska…”, emphasizing the off-beat. While “Manny Oh” was Jamaican-flavored R&B, “Easy Snappin'” was distinctly blues-infused ska.
[Excerpt: Theo Beckford, “Easy Snappin’”]
Prince Buster, a staunch Black nationalist and Rastafarian, sought to create a purely Jamaican sound. He incorporated Rastafarian Nyabinghi drumming into The Folkes Brothers’ “Oh Carolina,” featuring the legendary Count Ossie. This fusion of Rasta rhythms with Jamaican R&B marked another crucial step in ska’s evolution.
[Excerpt: The Folkes Brothers, “Oh Carolina”]
1962 was a transformative year for Jamaican music and the nation, marking Jamaica’s independence. It also saw the first recordings of a fourteen-year-old Millie Small, who would become ska’s first international superstar, thanks to her lollipop song.
Millie Small’s talent was evident from a young age, winning the prestigious Vere Johns Opportunity Hour talent contest at twelve. Coxsone Dodd recognized her potential, particularly her voice’s resemblance to Shirley Goodman of the New Orleans R&B duo Shirley and Lee.
Shirley and Lee, known for hits like “Sweethearts” and “Feel So Good,” were popular in Jamaican sound systems. Dodd aimed to create a Jamaican version, pairing Millie with Owen Gray. Their collaboration, “Sit and Cry,” blended Shirley and Lee’s vocal style with “The Twist” melody.
[Excerpt: Owen and Millie, “Sit and Cry”]
After Owen Gray pursued a solo career, Millie teamed up with Roy Panton. “We’ll Meet” by Roy and Millie soared to number one in Jamaica.
[Excerpt: Roy and Millie, “We’ll Meet”]
Meanwhile, Britain was experiencing a growing fascination with Caribbean music, especially ska. Post-war immigration from the Caribbean had significantly increased Britain’s Black population, creating a demand for their music. Chris Blackwell, from the privileged Crosse and Blackwell family, who had spent his youth in Jamaica and developed a passion for its culture, became a key figure in bringing ska to Britain.
Blackwell founded Island Records in 1959, initially focusing on Jamaican music. He had early success with Laurel Aitken’s “Boogie in My Bones.”
[Excerpt: Laurel Aitken, “Boogie in My Bones”]
After a brief detour working on the first James Bond film, Blackwell refocused on Island Records, becoming a distributor of Jamaican music in the UK. He would personally deliver records to shops in immigrant communities. While Island wasn’t the largest Jamaican music label in Britain – Blue Beat Records held that position, even becoming synonymous with ska itself – Blackwell played a crucial role in popularizing the genre. Local ska scenes were emerging in Britain, with Jamaican musicians and British R&B groups embracing the sound. Ezz Reco and the Launchers’ cover of Jimmy Cliff’s “King of Kings” became the first ska track to chart in the UK.
[Excerpt: Ezz Reco and the Launchers, “King of Kings”]
The Migil Five, a white British R&B band with Rolling Stone Charlie Watts’ uncle, further propelled ska into the mainstream with their top ten hit “Mockingbird Hill,” a ska rendition of a Les Paul and Mary Ford song.
[Excerpt: Migil Five, “Mockingbird Hill”]
By March 1964, ska’s influence was undeniable. Even The Beatles incorporated ska rhythms into “I Call Your Name.”
[Excerpt: The Beatles, “I Call Your Name”]
It was in this climate that Chris Blackwell brought Millie Small to the UK. Recognizing her potential, he promised her mother stardom. Instead of Island Records, Blackwell licensed Millie’s recordings to Fontana, a larger British label for wider distribution. Her first Fontana single, “Don’t You Know,” was conventional British pop and failed to chart.
[Excerpt: Millie, “Don’t You Know”]
For her second single, Blackwell recalled “My Boy Lollipop,” an American song by Barbie Gaye that was popular in Jamaican sound systems. Written by Robert Spencer of The Cadillacs, the rights to the song had a somewhat convoluted history involving card games and music industry figures. Barbie Gaye’s original 1956 recording, while not a hit in the US, had found its way to Jamaica.
[Excerpt: Barbie Gaye, “My Boy Lollipop”]
Blackwell enlisted Ernest Ranglin to create a ska arrangement for Millie’s version. Ranglin hired Jimmy Powell and the Five Dimensions (formerly The Moontrekkers) for the backing track. Ranglin replaced the saxophone solo with a harmonica solo, aligning with the harmonica’s popularity in British pop. While Rod Stewart, then with the Five Dimensions, is often credited with the harmonica solo, he denies playing on the track, with Millie maintaining it was indeed Stewart.
[Excerpt: Millie, “My Boy Lollipop”]
Released in early 1964, “My Boy Lollipop” became a global phenomenon, reaching number two in both the UK and US charts. Millie Small became an overnight star, appearing on UK television specials and even alongside The Beatles. Her follow-up single, “Sweet William,” reached number thirty, signaling a decline in mainstream white audiences’ initial ska craze.
[Excerpt: Millie, “Sweet William”]
Despite numerous attempts to revive her chart success, Millie’s subsequent releases had limited impact. A re-recording of “Bloodshot Eyes,” with the violent lyrics removed, reached number forty-eight in the UK.
[Excerpt: Millie, “Bloodshot Eyes”]
Collaborations with Jimmy Cliff and Jackie Edwards, and even an attempt to team her with the Spencer Davis Group, failed to reignite her stardom.
[Excerpt: Millie and Jimmy Cliff, “Hey Boy, Hey Girl”]
[Excerpt: Jackie and Millie, “Pledging My Love”]
[Excerpt: The Spencer Davis Group, “I’m Blue (The Gong Gong Song)”]
Millie continued recording into the early 1970s, even releasing “Enoch Power,” a protest song against racial prejudice.
[Excerpt: Millie Small, “Enoch Power”]
Despite her groundbreaking success with the lollipop song, Millie Small faced financial hardship for much of her later life. A brief resurgence of interest arose in the early 1980s when Bad Manners had a hit with a gender-swapped cover, “My Girl Lollipop.”
[Excerpt: Bad Manners, “My Girl Lollipop”]
However, Millie remained retired from performing after the early 1970s, living a private life until her death in 2020 at the age of seventy-two. Recognized and honored in Jamaica, including being named a Commander in the Order of Distinction, Millie Small, the voice behind the lollipop song that launched ska onto the world stage, never truly reaped the financial rewards of her immense contribution to music history. Her legacy, however, as a pioneer and the voice of a musical revolution, remains undeniable.
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