More than six decades after Millie Small took “My Boy Lollipop” to No. 2 on the Billboard Hot 100 in 1964, no Jamaican woman has surpassed the pioneering singer’s historic peak. As of October 2026, the record has stood for 62 years, making Small the benchmark for Jamaican women on America’s premier singles chart.
At 17 years old when she first entered the Billboard Hot 100 with “My Boy Lollipop,” Millie Smalls also remains the youngest Jamaican woman to chart on the Billboard Hot 100 in history.
The song debuted at No. 90 on May 23, 1964, and eventually climbed to No. 2 on July 4, 1964.
The woman who has come closest is Lady Saw, whose appearance on No Doubt’s “Underneath It All” reached No. 3 in 2002. That achievement came 38 years after Small established the record and remains the second-highest Hot 100 peak for a song featuring a Jamaican woman. Diana King follows with “Shy Guy,” which reached No. 13 in 1995.
The latest Jamaican woman to join the Hot 100 is Shenseea, who earned her first credited entry when the “Shake It to the Max (FLY)” remix with Moliy, Silent Addy and Skillibeng entered the chart in 2025. The song subsequently reached No. 44. Before Shenseea, the most recent Jamaican woman to enter was Grace Jones, whose Beyoncé and Tems collaboration “Move” debuted and peaked at No. 55 in 2022.
That means there was a three-year gap, from 2022 to 2025, between the Hot 100 appearances of Grace Jones and Shenseea. Jones’ 2022 appearance itself was a major comeback: “Move” marked her first Hot 100 entry in 35 years.
With 27 entries total, Patra and Grace Jones are tied with four credited songs each. Patra charted with “Worker Man,” “Romantic Call,” “Pull Up to the Bumper” and “Scent of Attraction,” while Jones has “Sorry/That’s the Trouble,” “I Need a Man,” “I’m Not Perfect (But I’m Perfect for You)” and “Move.”
