📖 Biography

Millicent Dolly May Small was born on 6 October 1947 in Vere, in the parish of Clarendon, Jamaica, the youngest of twelve children. Her father was an overseer on a sugar plantation. She knew she wanted to be a singer, and moved to Kingston as a teenager, where she auditioned for the producer Coxsone Dodd's Studio One. She was one of the few female singers in the early ska era, and recorded duets with Roy Panton as Roy and Millie, with a hit, We'll Meet.

The Island Records founder Chris Blackwell, who had grown up in Jamaica, heard her records and took her to England in late 1963, when she was 16, becoming her mentor and manager. After several recordings that made little impact, he chose My Boy Lollipop, a 1956 song by Barbie Gaye, for her fourth. Arranged by the Jamaican guitarist Ernest Ranglin, with its shuffle beat, it was recorded in London in the new bluebeat style.

Released in March 1964, with her credited simply as Millie, the record was a sensation. It reached number two on both the UK and US charts, selling six to seven million copies worldwide. It was the first major hit for Island Records, although it was released on the Fontana label, and the first ska hit to cross over, Jamaica's first million-selling single and the record that introduced ska to the world.

At 17 she travelled the world as a pop star, with Blackwell as her chaperone, becoming a sensation on British television, where her sparky personality and dancing charmed audiences. When she flew to the United States the flight was nicknamed the Lollipop Special, and she was greeted by crowds of fans. She had other hits, among them Sweet William, but none matched the success of Lollipop. Many believe it opened the door for Jamaican artists such as Bob Marley.

Jamaica awarded her a Medal of Appreciation in 1987 and, in 2011, the Order of Distinction in the rank of Commander for her contribution to Jamaican music. My Boy Lollipop was played at the opening ceremony of the 2012 London Olympics. Millie lived in Shepherds Bush, in west London, for the last two decades of her life, and died on 5 May 2020 after a stroke, survived by her daughter, the singer Jaelee Small. A blue plaque honours her in Shepherds Bush.

🕰️ Timeline
1947
Born in Clarendon, Jamaica.
1963
Brought to England by Chris Blackwell.
1964
My Boy Lollipop reaches number two in the UK and US.
1987
Receives Jamaica's Medal of Appreciation.
2011
Awarded the Order of Distinction.
2012
Her song plays at the London Olympics opening ceremony.
2020
Dies in London.
✦ Achievements
  • ◆My Boy Lollipop reached number two in the UK and the US
  • ◆Sold six to seven million copies worldwide
  • ◆First major hit for Island Records
  • ◆Jamaica's first million-selling single
  • ◆Pioneer of ska's international breakthrough
"
She lit the fuse for Jamaican ska music.
— Vas Blackwood, on Millie Small
🕊️ Legacy
Millie Small was the first Caribbean pop star to conquer the international charts, and My Boy Lollipop opened the way for Island Records and for the global rise of Jamaican music.
💡 Leadership Lessons
  • →Be ready when the chance comes. A teenager from Clarendon seized her chance in London and changed the charts.
  • →One song can open a door for many. Her success helped open the way for reggae and the artists who followed.