From ska to dancehall, reggae to pop-infused anthems, Jamaican-born women have made historic entries on the Billboard Hot 100, shaping the global appeal of Caribbean music. Millie Small was the first in 1964 with “My Boy Lollipop,” and in 2025, Shenseea became the latest Jamaican-born woman to make her mark on the Billboard Hot 100, debuting this week with “Shake It to the Max (FLY)” at No. 91.
Before Shenseea, the last Jamaican woman to hit the Hot 100 was Grace Jones in 2022 on the Beyoncé track “Move,” which peaked at No. 55 and stayed on the chart for one week.
With Patra and Jones tying for the most entries, together, these women represent decades of Caribbean influence on global pop culture.
1. Shenseea (Last chart: 2025)
Uncredited: “OK OK” – Kanye West (2021) – #12
Uncredited: “Pure Souls” – Kanye West & Roddy Ricch (2021) – #52
Official: “Shake It to the Max (FLY)” with Moliy & Skillibeng (2025) – #91
The newest addition to this lineage, Shenseea’s Billboard presence confirms her global breakout.
2. Grace Jones (2022)
“I’m Not Perfect (But I’m Perfect for You)” (1986) – #69
“Sorry / That’s The Trouble” (1977) – #71
“I Need a Man” (1977) – #83
“Move” – Beyoncé feat. Grace Jones & Tems (2022) – #55
The original genre-bender, Grace Jones fused art, fashion, and music into her groundbreaking entries.
3. Nyla (2016)
“Light It Up” – Major Lazer ft. Nyla & Fuse ODG (2016) – #73
Formerly of Brick & Lace, Nyla’s solo turn on this EDM banger earned her Billboard stripes.
4. Ms. Thing (2004)
“Dude” with Beenie Man (2004) – #26
Her bold and confident delivery helped this dancehall anthem dominate global charts.
5. Sasha (2003)
“I’m Still in Love with You” with Sean Paul (2003) – #14
A nostalgic duet that remains one of the biggest reggae revival tracks of the 2000s.
6. Lady Saw (2002)
“Smile” with Vitamin C (1999) – #18
“Underneath It All” with No Doubt (2002) – #3
The Queen of Dancehall crossed into pop and rock, scoring major success alongside No Doubt.
7. Chevelle Franklyn (1997)
“Dancehall Queen” with Beenie Man (1997) – #90
An anthem for empowered women, this title track from the cult film defined dancehall in the late ’90s.
8. Diana King (1997)
“Shy Guy” (1995) – #13
“I Say a Little Prayer” (1997) – #38
“Ain’t Nobody” (1995) – #88
Fusing reggae, pop, and R&B, Diana King became a global star through film soundtracks and radio hits.
9. Patra (1996)
“Worker Man” (1994) – #53
“Romantic Call” ft. Yo-Yo (1994) – #55
“Pull Up to the Bumper” (1995) – #60
“Scent of Attraction” ft. Aaron Hall (1996) – #82
Patra brought boldness and crossover appeal to U.S. airwaves, becoming a defining voice in ’90s dancehall.
10. Nadine Sutherland (1994)
“Action” with Terror Fabulous (1994) – #43
A fierce blend of charisma and chemistry, this duet became a staple of ’90s dancehall crossover success.
11. Dawn Penn (1994)
“You Don’t Love Me (No, No, No)” (1994) – #58
A haunting anthem turned timeless classic, reimagined for a new generation.
12. Marcia Griffiths (1990)
“Electric Boogie” (1990) – #51
The eternal party hit known for inspiring the Electric Slide, it’s a cultural treasure.
13. Millie Small (1964)
“My Boy Lollipop” (1964) – #2
“Sweet William” (1964) – #40
The original Jamaican Billboard queen—her ska smash cracked the U.S. Top 10 and opened doors worldwide.
Honorable mentions: Melody Makers (1991)
“Tomorrow People” (1988) – #59
“Good Time” (1991) – #85
Featuring Cedella and Sharon Marley, the family band helped carry reggae into a new era.
