Jamaican Artists With The Most Songs On The Billboard Hot 100, Ranked

Since 1964, Jamaicans have netted 134 entries on Billboard’s Hot 100 chart. Of these songs, 56 leaped into the Top 40, and 11 soared to No. 1 — placements that affirm Jamaicans’ ability to not only compete among the global titans of music, but win. 

The Hot 100 is a crucial signpost for any artist vying for mainstream popularity. The chart tracks the reach and replay value of songs in the U.S. — the world’s most valuable music market — and then pits the top one hundred against each other in a weekly contest for the No. 1 spot. Billboard draws its weekly winners from three sources: radio airplay, retail and digital singles sales, and, as of 2011, digital streams.

The system holds a steady allure for many. Since Billboard debuted the Hot 100 in 1958, placements have been accepted as standard units of pop success across the globe with the upper tiers promising exclusive doses of opportunity and triumph for the select few who ascend. Naturally, as the Hot 100 is an American chart, the spread of entries leans heavily towards American artists. But that fact alone hasn’t stopped outsiders from trying. 

Here are the Jamaican artists with the most songs on the Billboard Hot 100. The numbers beside each song entry denote the song’s peak position on the chart. 

Tanto Metro & Devonte (2)

Dancehall duo Tanto Metro & Devonte jumped into the mainstream after first leaning into the market-tested appeal of contrasts. The friction between Tanto Metro’s gruff verses and Devonte’s sunny melodies may have raised a few eyebrows on first listen but, as the numbers prove, they stuck. 

Entries: Give It To Her (85); Everyone Falls in Love (88)

T.O.K. (2)

Boasting a blend of falsetto hooks and streetwise deejaying, the four members of T.O.K. carved out a niche for themselves as Jamaica’s premier Dancehall boy band. As a testament to their range, the group greeted the Hot 100 with two very different offerings: the rootsy dirge, Footprints, and the Diwali riddim party anthem, Galang Gal.

Entries: Footprints (93); Galang Gal (88)

Peter Tosh (2)

Now, nearly forty years after his death, Peter Tosh is largely remembered by fans for the spirituality, indignation, and militancy that colored so much of his music. These weren’t the songs that lent themselves to the Hot 100, however. Don’t Look Back, his first entry, is a breezy cover of a Temptations song performed with the English rock star, Mick Jagger. His second charting single was a re-imagined, Jamaicanised version of Johnny B. Goode which, though a better indicator of the singer’s sharp wit and musical skills, still fell short of carrying Tosh’s potent truths to a mainstream audience.

Entries: (You’ve Got To Walk And) Don’t Look Back (81); Johnny B. Goode (84)

Cham (2)

Everything about Ghetto Story is legendary: from Cham’s menacing street imagery to Dave Kelly’s haunting riddim to the thought that this grim tale became a de facto “pop hit” when it kicked down the door on the Hot 100. The feat is made all the more amazing by the fact that the song burst onto the singles chart not once, but twice, with Alicia Keys offering an assist on its second go.

Entries: Ghetto Story (99); Ghetto Story Pt 2 (77)

Capleton (2)

In the mid-90s, Capleton added dimensions to Dancehall’s newly-found global presence with a pair of message-bearing songs, Tour and Wings of the Morning. Though the tracks were hits in their own right, Capleton’s label, Def Jam, figured that refitting them with some boom-bap drums and a feature from Method Man on Wings couldn’t hurt their commercial prospects. Their hunch proved correct. 

Entries: Tour (57); Wings of the Morning (79)

Rvssian (2)

After stacking his résumé with production credits on a fistful of Vybz Kartel hits, Rvssian began shuttling between genres and markets. The St. Andrew native snagged his first placement with Krippy Kush alongside Latin trap emissaries Bad Bunny and Farruko and his second with Writing On the Wall with rappers Cardi B, Post Malone, and French Montana.

Entries: Krippy Kush (75); Writing On the Wall (56)

Damian “Jr Gong” Marley (2)

If there’s any conclusion to be drawn from Jr Gong’s Hot 100 entries it’s this: if the Jamaican firebrand is heading to the charts, he’s bringing his fellow countrymen with him. By way of direct samples, interpolations, and production credits, Welcome to Jamrock and Jay-Z’s Bam feature contributions from no less than a dozen other Jamaicans including Ini Kamoze, Sister Nancy, Sly & Robbie, Jacob Miller, and Brigadier Jerry, among others. 

Entries: Welcome to Jamrock (55); Bam (47)

Ziggy Marley & The Melody Makers (2)

Soon after Bob Marley’s death in 1981, his eldest children found themselves under the weight of an enormous mandate: carrying on the revolutionary work started by their father. As Ziggy Marley & The Melody Makers, the quartet got to work. Two Grammy wins, a pair of Hot 100 entries and a decade later, the group had all the institutional validation they needed to know that their socially conscious strain of pop-reggae was reaching the masses. 

Entries: Tomorrow People (39); Good Time (85)

Ky-Mani Marley (2)

In the ’90s, America’s renewed love affair with Jamaican music stretched all the way to the cinema. This bode well for Ky-Mani Marley who picked up hits as a feature on the soundtracks for the Hollywood comedies “Money Talks” and “Senseless.”

Entries: Gotta Be…Movin’ On Up (90); Avenues (35)

Shenseea (2)

Shenseea has long-touted her pop star ambitions. “By next year, I want to be international,” she said in 2018. “In five years, I will be an international artist,” she affirmed in 2020. After building enough momentum through a career-spanning grind, the stars aligned and Kanye West enlisted her for two features on his 2021 LP, Donda. In addition to being included in one of the album’s live debuts, Shenseea landed her first set of Hot 100 hits: Pure Souls, which peaked at No. 52 and OK OK Pt 2 which peaked at No. 12. 

Entries: Pure Souls (52); OK OK Pt 2 (12)

Lady Saw (2)

After revamping the rules and attitudes of the male-dominated Dancehall scene to the benefit of its women participants, Lady Saw earned herself a few victory laps. One of these came as a Hot 100 entry for a guest toast on Vitamin C’s bubbly single, Smile. Her triumph ballooned as a feature on No Doubt’s Underneath It All won the deejay a No. 3 spot on the chart and a Grammy for Best Pop Performance by a Group with Vocals. If Dancehall was going mainstream, so was its Queen. 

Entries: Smile (18); Underneath it All (3)

Millie Small (2)

At age 16, Millie Small introduced Jamaican music to the world. Carried by Small’s distinctively high-pitched voice, 1964’s My Boy Lollipop was the first smash hit of the fast-developing Ska genre, drawing foreign eyes and ears to the culture and sounds of a newly independent Jamaica. Though the song fell one spot short of clinching the No. 1 position, its impact had nevertheless secured a place for Millie Small and Ska in the pop history books. 

Entries: My Boy Lollipop (2); Sweet William (40)

Ini Kamoze (2)

From the mid to late 80s, Reggae singer Ini Kamoze cemented himself as one of the most compelling voices to emerge from a hotbed of evolving sounds. After 1988’s Shocking Out, however, the LPs stopped flowing. His next album was 1995’s Here Comes the Hotstepper, titled and promoted as a follow-up to his show-stopping single of the same name. Between Kamoze’s flashy lyrics, his sterling flow and the sample-laden production by Salaam Remi, Here Comes to Hotstepper boasts a kaleidoscope of ideas clearly primed for the Hot 100’s top spot. 

Entries: Here Comes the Hotstepper (1); Listen Me Tic (Woyoi) (88)

Carl Douglas (2)

With Kung Fu Fighting, Carl Douglas managed to produce a disco hit too campy to overlook and too catchy to escape. Here was this Jamaican ex-pat living in England, singing a song about “funky Chinamen from funky Chinatown,” and donning stereotypical Chinese garb, effectively going all in to market this novelty song. People loved it. So much so, in fact, that the song scored Douglas the distinction of being the first Jamaican-born singer with a No. 1 on the Hot 100.

Entries: Kung Fu Fighting (1); Dance the Kung Fu (48)

Grace Jones (3)

Grace Jones’ uncompromising will is at the heart of everything she does. It’s the engine that drove her from modeling to acting and from experimenting with music to soaring up the charts. It’s also what allowed her to shift between eras, going from making a splash with disco hits like I Need A Man and Sorry to embracing her home’s patent rhythms in her early 80’s output.

Entries: I Need A Man (83); Sorry/That’s The Trouble (71); I’m Not Perfect (69)

Super Cat (3)

Super Cat has never aimed to appease. The fact that his unflinching Dancehall flows crashed through American speakers and were not only accepted but welcomed, proves that his bets paid off. From track to track, his frenetic, whirlwind delivery found a home among funk-fuelled hip-hop (Alright) and libido-drenched R&B (Na Na Na Na) as easily as it did on the Jamaican sound system circuit. He even scored a hit in Fly with the rock band Sugar Ray (the song topped the Hot 100 Airplay chart but was deemed ineligible for the Hot 100 owing to a formality.) By refusing to dilute his style, Cat made it clear to artists and audiences alike that if they can’t keep up, that’s their problem, not his.

Alright (19); Girlstown (99); Na Na Na Na (75)

Elephant Man (3)

Elephant Man put his faith in novelty and reaped the rewards. With an eye-grabbing appearance, a deep and lisping voice, and electric dance moves, he made it all but impossible to miss him. And with music as infectious as Pon De River, why would you want to? 

Entries: Pon De River (86); Jook Gal (57); Whine Up (29)

Jimmy Cliff (3)

Jimmy Cliff pushed Jamaican music to new heights. Whether he wrote about societal ills as in Wonderful World, Beautiful People, or romance as in Come Into My Life, Cliff’s message found a way to connect with ears at home and abroad. That fact, along with his role as a star and composer for the 1972 film, “The Harder They Come,” helped secure a place for then-burgeoning Reggae music in the ever-widening field of pop music. 

Entries: Wonderful World, Beautiful People (25); Come Into My Life (89); I Can See Clearly (18)

Bounty Killer (3)

In the ’90s, New York hip-hop’s vanguard brought Bounty Killer into the fold. The Dancehall star appeared on tracks with AZ, Busta Rhymes, and Swizz Beats and scored hits with the Fugees (Hip-Hopera) as well as Mobb Deep and Big Noyd (Deadly Zone). On paper, these collaborations made sense. Perhaps that’s why when the opportunity to pivot came, he took it. His feature on No Doubt’s Hey Baby came as a surprise but a welcome one: It hit the charts at full tilt, scoring the deejay the highest charting single of his career and a subsequent Grammy win.

Entries: Hip-Hopera (81); Deadly Zone (79); Hey Baby (5)

Diana King (4) 

Years of musical give-and-take between Jamaica and the U.S. found a vessel in Diana King. Patois-laden toasts blended seamlessly into shimmering, soulful choruses, all connected by King’s regal voice and launched into orbit by a multiplying audience. The mold-breaking Spanish Town native even found commercial success with their dance track, I Say A Little Prayer.

Entries: Shy Guy (13); Ain’t Nobody (94); I Say a Little Prayer (38); L-L-Lies (71)

Patra (5)

Patra launched and sustained her early-90’s Hot 100 run through sheer force. From her first brush with the mainstream on Shabba Ranks’ Family Affair, the deejay erupted with a thundering Dancehall style that boomed with her signature bravado. Even on the glossy R&B production of songs like Scent of Attraction, her fiery vocals and confidence make themselves at home like a conquering army marching under a foreign sky.

Entries: Family Affair (84); Worker Man (53); Romantic Call (55); Pull Up to the Bumper (60); Scent of Attraction (82)

Shabba Ranks (5)

Shabba’s rise ushered a new breed of Jamaican superstar into the mainstream: the Dancehall deejay. With a deep, brash voice and ribald lyrics to match, Shabba set out to dominate international markets. To that end, songs like Mr Loverman and Slow And Sexy shot up the charts, delighting many listeners and shocking others. His legacy extends beyond the development or acceptance of Dancehall; to this day, there are few names as frequently referenced in hip-hop culture as Shabba’s.

Entries: Housecall (37); Mr Loverman (40); Slow And Sexy (33); Family Affair (84); Let’s Get It On (81)

Inner Circle (5)

After re-grouping in the late ‘80s, roots outfit Inner Circle began producing songs sticky enough to land on the charts. The most enduring of these, Bad Boys, struck a receptive chord with legions of listeners, but perhaps not for the reasons the band intended. The song soundtracks the long-running and controversial American TV Show, Cops, which may have created a sour association for some, but it guaranteed the group a place in the pop culture hall of fame.

Entries: Bad Boys (8); Sweat (A La La La La Long) (16); Rock With You (98); Games People Play (84); Not About Romance (92)

Beenie Man (6)

By the time Beenie Man had hit the Hot 100 with Dancehall Queen in 1997, he was already a veteran deejay with nearly twenty years of experience under his belt. He was also 24 years old. His life-long ascent to the top of the local food chain left him looking to the American mainstream for new hurdles to clear. Whether it was pairing his witty lyricism and wizard-like flows with sultry female hooks as on Girls Dem Sugar and Feel It Boy or holding the spotlight on his own as on Who Am I and King of the Dancehall, Beenie Man had found his winning formulas. By the end of his run, he had snagged six Hot 100 entries, peaking at No. 26 with Dude. 

Entries: Dancehall Queen (90); Who Am I (40); Girls Dem Sugar (54); Feel It Boy (28); Dude (26); King of the Dancehall (80)

Maxi Priest (7)

Sticking to the tradition of London’s native lovers rock scene, Maxi Priest committed himself to the career-long role of lovestruck protagonist. Where he strayed, however, was in his sound. Beginning with Wild World, the singer’s steely raps and impassioned singing found a home among a global audience that hoped to see how far one could stretch this Reggae-infused style of R&B.

Entries: Wild World (25); Close to You (1); Just a Little Bit Longer (62); Set the Night to the Music (6); Housecall (37); Groovin’ In the Midnight (63); That Girl (20)

Shaggy (8)

Since the dawn of his career, Shaggy seemed unconcerned with tailoring his sound to anything but the global masses. His hits plucked from oldies and refitted them with modern sounds (Oh Carolina); slowed down a typically rapid-fire Dancehall cadence (Boombastic); and flirted with the irreverent (It Wasn’t Me). He built his own lane and it paid off; he became the best-selling Dancehall artist of all time. 

Entries: Oh Carolina (59); Boombastic/In the Summertime (3); That Girl (20); Piece of My Heart (72); Luv Me, Luv Me (76); It Wasn’t Me (1); Angel (1); I Need Your Love (66)

Sean Kingston (14)

In the three years following the breakout of Beautiful Girls in 2007, Sean Kingston was inescapable. He was like a human hit factory churning out single after single and saturating the charts with his mix of pop and hip-hop. The machines had to grind to a halt eventually and when they did, the singer had fourteen Billboard-certified songs to his name.

Entries: Beautiful Girls (1); Me Love (14); Love Like This (11); Take You There (7); What Is It (57); Roll (61); There’s Nothin’ (60); Fire Burning (5); Face Drop (61); Feel It (78); Eenie Meenie (36); Letting Go (Dutty Love) [36]; Dumb Love (84); Beat It (52)

Sean Paul (19)

With every entry that Sean Paul supplies to the Hot 100, he strengthens his claim to one of the most elusive goals of pop stardom: longevity. Within three years of first making landfall on the Hot 100 in 2002, Sean Paul scored three No. 1s with Get Busy, Baby Boy, and Temperature, making him a household name in the U.S. and worldwide. His fourth No. 1 came over a decade later with Cheap Thrills, but there were plenty of placements dotted throughout his unprecedented run. Sean Paul’s ability to make every release land like a blockbuster allowed him to change what it means to be a global superstar. 

Entries: Gimme the Light (7); Get Busy (1); Breathe (70); Like Glue (13); Baby Boy (1); I’m Still in Love With You (14); We Be Burnin’ (6); Temperature (1); (When You Gonna) Give It Up To Me (3); Break It Off (9); So Fine (50); Do You Remember (10); Shake Señora (69); Got 2 Luv U (84); She Doesn’t Mind (78); Bailando (12); Cheap Thrills (1); Rockabye (9); Subeme La Radio (81)

Honorable Mentions

• OMI — Cheerleader (1)
• Spragga Benz — Turn Me On (4)
• Desmond Dekker & The Aces — Israelites (9)
• Wayne Wonder — No Letting Go (11)
• Ms Thing — Dude (26)
• Buju Banton — Believe What I Say (28)
• Cutty Ranks — Dame Tu Cosita (36)
• Terror Fabulous & Nadine Sutherland — Action (43)
• Third World — Now That We Found Love (47)
• Bob Marley & The Wailers — Roots, Rock Reggae (51)
• Marcia Griffiths — Electric Boogie (51)
• Chaka Demus & Pliers — Murder She Wrote (57)
• Agent Sasco — The Blacker the Berry (66)
• Dawn Penn — You Don’t Love Me (No, No, No) (68)
• Junior Reid — It’s Okay (One Blood) (71)
• Gyptian — Hold You (77) 
• Sasha – I’m Still In Love With You (14)
• Prince Buster — Ten Commandments (81)
• Tarrus Riley & Walshy Fire — Powerful (83)
• Chevelle Franklyn — Queen of the Dancehall (90)
• Mr Vegas — Pull Up (98)
• Skillibeng — Crocodile Teeth (100)
• Stefflon Don – Alone (66)
• Mad Cobra – Flex (13)