After releasing a few Jamaican singles in 1962, Small caught the attention of Island Records founder Chris Blackwell, who was living in Jamaica at the time. He became her legal guardian and manager and took her to London in 1963. In 1964, Small released an Ernest Ranglin rearrangement of the 1956 song "My Boy Lollipop," which became her biggest hit.
“My Boy Lollipop” peaked at No. 2 on the Hot 100 (chart dated July 4, 1964). Another of her hits, "Sweet William," peaked at No. 40 on the Sept. 5, 1964-dated chart. Her album My Boy Lollipop also peaked at No. 132 on the Billboard 200 on Aug. 29, 1964.
Blackwell also said in a statement: “Millie opened the door for Jamaican music to the world. It became a hit pretty much everywhere in the world. 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 really sweet person, very funny, great sense of humour. She was really special.”
Small is survived by her daughter Jaelee.