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More than six decades later, Millie Small’s “My Boy Lollipop” remains a landmark for Jamaican women on the Billboard Hot 100.
The song peaked at No. 2 in 1964, a record no Jamaican woman has surpassed.
As of October 2026, Small’s achievement has stood for 62 years.
At just 17, she also became the youngest Jamaican woman to chart on the Billboard Hot 100.
“My Boy Lollipop” debuted at No. 90 on May 23, 1964, before reaching No. 2 on July 4.