35 Singers From the Caribbean Who Made It Big in

Posted On: March 9, 2021
Comments: 0

FlourishAnyway believes there is a playlist for just about any situation and is on a mission to unite and entertain the world through song.

We associate the Caribbean with beautiful beaches, a carefree attitude, and music. Find out which famous singers and bands got their start in the island paradise of the Caribbean.

Rowan Heuvel via Unsplash, Free Domain, modified by FlourishAnyway

Caribbean Island Musicians Who Made It Big in America

There certainly are worse places to be from than the stunning tropical paradise that is the Caribbean! (Okay, sure, there’s Hurricane Alley, but not all of the 13 sovereign island nations and 12 dependent territories that comprise the Caribbean lay within this hurricane-prone zone.)

The Caribbean islands beckon tourists from across the globe, as they are blessed with powdery white sand beaches, palm trees, waterfalls, and wildlife. The islands offer vacationers snorkeling, fruity drinks, nightlife, and dazzling music, ranging from reggae to calypso to salsa.

Some of the most talented singers and bands that have made it big in America have come from the islands of the Caribbean. Find out which famous singers got their start in this tropical paradise. You might be surprised.

1. Rihanna (Barbados)

It’s been a long climb for an island girl from Barbados to the top of the worldwide music charts. Pop and R&B superstar Rihanna came from modest beginnings. Growing up in Barbados, she struggled with an unstable family environment, faced down personal illness, and never graduated from high school.

However, upon being discovered by an American record producer in 2003, the young songbird left her past behind. After wowing Jay-Z, she was quickly signed to his Def Jam Recordings music label.

In 2010, Rihanna set a Guinness Book world record as the female artist with the most US number-one singles in a year. By 2019, she had become the richest female musician in the world and had snagged multiple Grammy Awards along the way. Her long list of number one hits include:

“SOS” (2006)

“Umbrella” (2007)

“Take a Bow” (2008)

“Live Your Life” (2008)

“Disturbia” (2008)

“Rude Boy” (2010)

“Only Girl (In the World)” (2010)

“What’s My Name?” (2010)

“Love the Way You Lie” (2010)

“S&M” (2011)

“We Found Love” (2011)

“Diamonds” (2012) and

“Work” (2016)

Unfortunately, no one can completely separate themselves from their past. The domestic violence that Rihanna’s father had once inflicted upon her mother proved to be a dangerous pattern. In 2009, the singer was physically assaulted by then-boyfriend and fellow R&B singer Chris Brown (who himself grew up with domestic violence at home). Brown pleaded guilty to felony assault then in 2012, the two reconciled and briefly dated before breaking up again.

2. Bob Marley (Jamaica)

Hey mon, Bob Marley was not simply a Jamaican reggae singer but instead a trailblazer for the genre. He was also a cultural phenomenon, a symbol of Jamaica, and a Rastafari icon. Marley released reggae, ska, and rocksteady music as a solo artist as well as collaboratively with others. Specifically, in 1963 he formed a group called Bob Marley and the Wailers, together with Peter Tosh and Bunny Wailer, later adding other Jamaican musicians.

Five of Marley’s albums are on Rolling Stone’s list of “500 Greatest Albums of All Time.” However, “Roots, Rock, Reggae” (1976) was, in fact, the only single to reach the US Billboard Hot 100. The following songs found minor success at the time on the R&B and/or dance charts:

“Exodus” (1977)
“Waiting in Vain” (1978)
“Could You Be Loved” (1980) and
“Sun Is Shining” (1999).

Bob Marley had 11 acknowledged children with seven different women prior to his death from melanoma at age 36. Some of these children, such as his first child, Ziggy, have ventured into the performing music business like their father.

3. Nicki Minaj (Trinidad and Tobago)

Nicki Minaj is known for her colorful wigs, costumes, and her accents as much as she is for her sexually provocative lyrics and rapid-paced vocals. Some people regard the singer and rapper as the “black Lady Gaga” for her fashion choices.

The future Queen of Rap was born in Port of Spain, the capital city of Trinidad and Tobago, to two part-time gospel singers. Sadly, her father was a violent drug addict who burned down the family’s home in an attempt to kill Minaj’s mother. Perhaps it was her disruptive childhood that prompted Onika Tanya Maraj-Petty to develop alter egos, other personas who could cope with her emotional needs. The family relocated to the Bronx in New York City when she was only five. Minaj spent her youth building her skills in acting and singing.

In 2009, the Trinidadian musician was discovered by rapper Lil Wayne and signed to a recording contract. She later appeared as a judge on American Idol and contributed to several major films. In 2017, the hip-hop artist set a Guinness Book of World Records for the most Billboard Hot 100 entries by a solo (female) artist. Amazingly, seven of Minaj’s singles were simultaneously on the chart. The Caribbean girl from the troubled family has become one of the most influential people in the world.

Minaj has experienced resounding success on the mainstream pop, R&B, and rap charts. Examples of some of her hits include the following:

“BedRock” (2009)

“Your Love” (2010)

“Right Thru Me” (2010)

“Moment 4 Life” (2010)

“Super Bass” (2011)

“Did It On’em” (2011)

“Pills n Potions” (2014)

“Anaconda” (2014)

“Only” (2014)

“Truffle Butter” (2015)

“No Frauds” (2017)

“MotorSport” (2017) and

“Chun-Li” (2018).

4. Gloria Estefan (Cuba)

Gloria Estefan is a native Cuban, born under the name of Gloria María Milagrosa Fajardo García. As a child, she fled Havana during the Cuban Revolution with her family for a better life in the United States. Her mother endeavored to support the family on a teacher’s salary after Gloria’s father was diagnosed with multiple sclerosis.

In 1975, the future Grammy Award winner met fellow Cuban musician Emilio Estefan, Jr. while his band (then called the Miami Latin Boys) performed at a wedding that Gloria and her cousin were attending as guests. When the girls sang two songs extemporaneously, the band asked them to join them as full-time vocalists. The group subsequently morphed into the Miami Sound Machine. Gloria and Emilio married three years later.

Decades after the Latin pop artist fled Cuba, she would earn accolades to include the Presidential Medal of Freedom, induction into the Songwriters Hall of Fame, and the American Music Award for Lifetime Achievement. Some of her most notable hits (credited as a solo artist or with the Miami Sound Machine) include:

“Conga” (1985)

“Bad Boy” (1986)

“Words Get in the Way” (1986)

“Rhythm Is Gonna Get You” (1987)

“Can’t Stay Away from You” (1988)

“Anything for You” (1988)

“Don’t Wanna Lose You” (1989)

” Here We Are ” (1990)

“Cuts Both Ways” (1991) and

” Coming Out of the Dark ” (1991).

5. Wyclef Jean (Haiti)

If you aren’t into rap music, perhaps you still might recognize Wyclef Jean as a featured artist from hits such as “No, No, No” by Destiny’s Child (1997) or Shakira’s “Hits Don’t Lie” (2006). Jean is a Haitian rapper and singer who relocated to the US with his family when he was only nine.

In the 1980s, the Caribbean native formed a hip-hop trio called the Fugees (short for “refugees”) with Lauryn Hill and fellow Haitian-American Pras Michel. They were met with moderate success. The group had one single break the Top 40 of the Billboard Hot 100, thereby technically making the Fugees a one-hit wonder. Before disbanding in 1997 to pursue solo careers, the Fugees placed several other songs on the R&B charts.

Examples of Jean’s solo shits include:

“We Trying to Stay Alive” (1997)

“Gone till November” (1997)

“911” (2000) and

“Two Wrongs” (2002).

In 2009, Jean enrolled in classes at the prominent Berklee College of Music but did not graduate. He also attempted to run for president in Haiti but was disqualified. The rapper has also been accused of stealing $16M from a charity he established to raise money for Haitian earthquake relief.

6. The Baha Men (The Bahamas)

Did we ever resolve who actually let the dogs out? This contagious ditty from 2000 (“Who Let the Dogs Out?”) was the first and only hit for the chill Caribbean group known as The Baha Men. They point out it actually has zero to do with dogs of the canine variety. Instead, it’s a man-bashing song, can you believe?

Although the tune was a global hit, it didn’t achieve significant success in the US until it was featured in the soundtrack for the animated film Rugrats in Paris: The Movie and became an anthem at athletic events. Then, it was ubiquitous. Ironically, the song won a Grammy Award but was also named to several “most annoying song” or “worst song ever” lists. Ah yepee ah yo! You can’t please everyone!

7. Boney M. (Aruba, Jamaica, Montserrat)

Sometimes groups that tear up the rest of the world are slow to impress an American audience. So was the case for Boney M.

During the disco era of the 1970s, the Euro-Caribbean vocal group was known throughout the world for hits such as “Daddy Cool” (1976), “Sunny” (1976), “Ma Baker” (1977), “Rasputin” (1977), and the Caribbean Christmas tune, “Mary’s Boy Child – Oh My Lord” (1978). They sold over 100 million records in all. However, in America, only “Rivers of Babylon”/”Brown Girl in the Ring” (1978) cracked the Top 40 of the Billboard Hot 100.

Boney M’s original lineup included members from three different Caribbean countries: Liz Mitchell and Marcia Barrett from Jamaica, Maizie Williams from Montserrat and Bobby Farrell from Aruba. Williams and Farrell never sang on the records but did sing in live performances. Their record producer was Frank Farian, the same German record producer who was behind the infamous duo Milli Vanilli in the early 1990s.

8. Heavy D (Jamaica)

Jamaican-born rapper Heavy D came into this world known as Dwight Arrington Myers, and even though his family moved to the US as a child, his music retained a Carribean influence. During the 1980s and 1990s, he performed as a solo artist, featured artist, and with his group of backup vocalists and dancers, dubbed Heavy D & the Boyz.

Some of his more prominent hits on the R&B and mainstream pop charts included:

“We Got Our Own Thang” (1989)

“Somebody for Me” (1989)

“Is It Good to You” (1991)

“Now That We Found Love” (1991)

“Got Me Waiting” (1994)

“Big Daddy” (1997)

“I’ll Do Anything” (1997) and

“Don’t Stop” (1999).

Heavy D was instrumental in influencing his music label to hire Sean “Diddy” Combs as an intern. It was Combs’ first big opportunity in the music industry.

“New brooms sweep clean, but ole brooms know de corners.” – Caribbean saying (Someone with a new perspective can make great changes, but experience is also very valuable.)

MabelAmber via Pixabay, FreeDomain modified by Flourish Anyway

9. Billy Ocean (Trinidad and Tobago)

If you remember that Grammy Award-winning 1984 pop song, “Caribbean Queen (No More Love on the Run,” then it only seems right that the man who sang it would be from the Caribbean himself. Billy Ocean is the stage name for Leslie Sebastian Charles, who was born in Trinidad. His father was a local calypso musician, and his mother also sang. The family moved to London when Ocean was 10 years old, and although he retains an island accent from his boyhood, today the vocalist regards himself as British.

Ocean placed singles on the American R&B and mainstream pop charts, including these hits:

“Love Really Hurts Without You” (1976)
“Loverboy” (1985)
“Suddenly” (1985)
“When the Going Gets Tough, the Tough Get Going” (1986)
“There’ll Be Sad Songs (To Make You Cry)” (1986)
“Love Zone” (1986)
“Love Is Forever” (1986) and
“Get Outta My Dreams, Get into My Car” (1988)

At the height of his fame, Ocean walked away from his career to help raise his three children.

10. T-Connection (The Bahamas)

The six-member funk/disco group T-Connection hailed from The Bahamas, and in the 1970s they made a splash on the American music scene. T-Connection enjoyed several crossover hits on the R&B and mainstream pop chart but saw more success on the disco/dance chart where their 1977 single, “Do What You Wanna Do,” was a number one hit. Examples of other successful singles include:

“Disco Magic” (1976)

“On Fire” (1977)

“Let Yourself Go” (1978)

“At Midnight” (1979)

“Saturday Night” (1979)

“Everything Is Cool” (1981) and

“A Little More Love” (1982).

11. Sean Kingston (Jamaica)

Reggae fusion and hip-hop artist Sean Kingston was born in America under the name Kisean Paul Anderson, but he moved to Jamaica as a young child. Music ran in his family; his grandfather was a major Jamaican record producer. Kingston borrowed his stage name from Jamaica’s capital since he is a Jamaican singer. Included among the islander’s hits on the Billboard Hot 100 chart are:

“Beautiful Girls” (2007)

“Me Love” (2007)

“Take You There” (2007)

“Fire Burning” (2009)

“Eenie Meenie” (2010) and

“Letting Go (Dutty Love)” (2010).

12. Natti Natasha (Dominican Republic)

You know you’ve made it when Rolling Stone proclaims you to be an artist that people need to know. Natti Natasha is a Dominican-born diva who has created a huge sensation on YouTube as well as on the US Latin music charts. This rising Spanish language recording star so far hasn’t crossed over to the mainstream Billboard Top 40. Some of Natasha’s biggest Latin hits include “Sin Pijama” (2018), “Me Gusta” (2018), and “No Lo Trates” (2019). Watch this one! Natasha could be tomorrow’s superstar!

13. Omi (Jamaica)

Known mononymously as Omi, Omar Samuel Pasley is a Jamaican singer whose single, “Cheerleader” was a worldwide smash hit in 2014. So far, he has been unable to follow up the success of the song with another hit in the US, thereby making him a one-hit wonder.

“Cheerleader” is a buoyant, tropical, and playful number that describes the narrator’s commitment to his significant other. Other women who might otherwise catch a man’s eye do not tempt this guy because he values his girlfriend’s physical beauty and the deep emotional support she provides him. There are some things that are irreplaceable.

14. Johnny Kemp (The Bahamas)

As an adolescent, Baha singer-songwriter Johnny Kemp emigrated from the Caribbean island where he was born and moved to Harlem in the US. He subsequently found minor success with two R&B hits, “Dancin’ With Myself” and “One Thing Led to Another.” In 1989, Kemp was nominated for a Grammy Award for “Just Got Paid” which reached the Top 10 of the US Billboard Hot 100 chart. Because this was his only single on the mainstream pop chart, Kemp is known as a one-hit wonder.

Sadly, the Baha singer died when he slipped on some rocks on a beach in Jamaica and drowned. He was in Jamaica with a cruise ship on which he was scheduled to perform.

15. Grandmaster Flash (Barbados)

If you’ve ever heard any of the following lines, then you have Grandmaster Flash and the Furious Five to thank:

“Throw your hands in the air, and wave ’em like ya just don’t care!”

“Clap your hands to the beat!” and

“Everybody say, ‘ho!’”

Grandmaster Flash is the nickname of a Jamaican-born recording artist who moved to the US as a child. Fueled by his father’s love of Caribbean music, he laid the foundations of the hip-hop genre by pioneering DJing, cutting, scratching, and mixing techniques. Grandmaster Flash became a protege of DJ Kool Herc, also a Jamaican immigrant. Herc is often credited as hip-hop’s first DJ.

In the early days of rap, rappers competed for each other’s equipment rather than prize money. Grandmaster Flash became one of the first DJs to be paid for his skills. In 2007, he and The Furious Five (the American musicians that supported him) became the first hip hop act to be inducted into the Rock & Roll Hall of Fame.

Among the hits that Grandmaster Flash and The Furious Five has racked up on the US Billboard Hot 100 and R&B are:

“Freedom” (1980)

“The Birthday Party” (1980)

“It’s Nasty (Genius of Love)” (1981)

“The Message” (1982)

“Scorpio” (1982) and

“New York New York” (1983).

Rolling Stone magazine ranked “The Message” on its list of “The 500 Greatest Songs of All Time.”

“A crab never forget he hole” – Caribbean saying (There’s no place like home.)

wilitocricri via Pixabay, Free Domain, modified by FlourishAnyway

Even More Caribbean Singers Who Made It Big in America

If you know of a Caribbean singer or band not listed here who has had some hits on the Top 40 US pop, rock, country, alternative or other major US Billboard chart, then leave a suggestion in the Comment Section below.

Artists & Their Countries	Examples of Popular Singles	Genres
16. Shontelle (Barbados)	T-Shirt (2008), Impossible (2010), Perfect Nightmare (2010), Say Hello to Goodbye (2011)	R&B
17. Shaggy (Jamaica)	Boombastic (1995), That Girl (1996), It Wasn’t Me (2000), Angel (2000),	reggaee, dancehall
18. Ini Kamoze (Jamaica)	Here Comes the Hotstepper (1994)	reggae, dancehall
19. Jimmy Cliff (Jamaica)	Wonderful World, Beautiful People (1969), I Can See Clearly Now (1993)	reggae, ska
20. Harry Belafonte (Jamaica)	Banana Boat (Day-O) (1957), Mama Look a Boo Boo (1957), Gomen Nasai (Forgive Me) (1953), Jamaica Farewell (1956), Mary’s Boy Child (1956)	calypso, R&B, pop
21. Carl Douglas (Jamaica)	Kung Fu Fighting (1974)	disco
22. Sean Paul (Jamaica)	Gimme the Light (2002), Get Busy (2003), We Be Burnin’ (2005), (When You Gonna) Give It Up to Me (2006)	reggae, dancehall
23. Bounty Killer (Jamaica)	Hey Baby (2001)	reggae, dancehall
24. Beenie Man (Jamaica)	Who Am I (Sim Simma) (1997), Feel It Boy (2002), Dude (2004)	reggae, dancehall
25. Bounty Killer (Jamaica)	Hey Baby (2001)	reggae, dancehall
26. Ricky Martin (Puerto Rico)	“Livin’ la Vida Loca” (1999), “She’s All I Ever Had” (1999), “Shake Your Bon Bon” (1999), She Bangs (2000), “No One Wants to Be Lonely” (2001)	pop, Latin
27. Menudo (Puerto Rico)	“If You’re Not Here By My Side” (1984)	pop rock, R&B
28. Daddy Yankee (Puerto Rico)	“Gasolina” (2004), Rompe (2005), “Con Calma” (2019), “Despacito” (2017)	hip-hop, Latin pop, dancehall
29. Camilla Cabello (Cuba)	“I Know What You Did Last Summer” (2015), “Bad Things” (2016), “Havana” (2017), “Never Be the Same” (2017), “Señorita” (2019)	pop, R&B
30. Luis Fonsi (Puerto Rico)	“Despacito” (2017)	Latin pop
31. José Feliciano (Puerto Rico)	“Light My Fire” (1968), “Hi-Heel Sneakers” (1968), “Feliz Navidad” (1970),	pop, soft rock
32. Grace Jones (Jamaica)	“Do or Die” (1978), “Pull Up to the Bumper” (1981), “Slave to the Rhythm” (1985), “I’m Not Perfect (But I’m Perfect for You)” (1986), “Love on Top of Love” (1989)	disco, new wave, industrial
33. Pepa (of Salt-N-Pepa) (Jamaica)	“Push It” (1987), “Shake Your Thang” (1988), “Expression” (1989), “Shoop” (1993), “Whatta Man” (1994),	pop, dance, hip-hop
34.Ini Kamoze (Jamaica)	“Here Comes the Hotstepper” (1994)	hip-hop, reggae
35. Iyaz (British Virgin Islands)	“Replay” (2009), “Solo” (2010)	elecgtro R&B

FlourishAnyway (author) from USA on August 11, 2020:

Lll – No, it’s my understanding that she is of Guyanese descent (her mother is Guyanese).

Lll on August 10, 2020:

Rihanna is half Bajan and half Guyanese

FlourishAnyway (author) from USA on July 08, 2020:

Rajan – I appreciate your stopping by. The world is certainly a global village, and people certainly travel far from home in their careers. It’s often a surprise to learn someone’s background.

Rajan Singh Jolly from From Mumbai, presently in Jalandhar, INDIA. on July 08, 2020:

Barring a few singers like Rihanna, Billy Ocean and a few others I was not aware of the other Caribbean singers who hit the big time in America. Thanks for adding to my knowledge.

FlourishAnyway (author) from USA on March 10, 2020:

Eloquent – Thanks for reading,

The Eloquent Heart Writer from Barbados W.I on March 10, 2020:

Thank you for sharing

FlourishAnyway (author) from USA on March 03, 2020:

Robert – Thanks for stopping by. It’s fun to take a look at artists and where they hail from. Some are a little surprising. Have a great day!

FlourishAnyway (author) from USA on March 03, 2020:

James – Glad you enjoyed this bunch of musicians. Got some Irish and Scots coming up later today.

Robert E Smith from Rochester, New York on March 03, 2020:

My taste in music is varied but I still didn’t recognize 2 or 3 artists. It was a fun exploration of great songs and some great memories. Bob.

James C Moore from Joliet, IL on March 03, 2020:

Yeah mon, a spectacular collection of musicians. I like practically everyone on here.. Gloria Estefan, the rhythm’s gonna get you is a long time favorite. My junior high music teacher introduced us to Harry Belafonte’s “Day-O daylight’s comin and I wanna go home.”

FlourishAnyway (author) from USA on February 27, 2020:

Genna – Thanks for stopping by. I’m glad you enjoyed this and hope this brightened your day.

Genna East from Massachusetts, USA on February 27, 2020:

Hi Fourish…

I had no idea that some of these artists hail from the Carribean. Who knew? Many thanks for the wonderful music. I’m smiling as I listen to an old fav — Bob Marely.

FlourishAnyway (author) from USA on February 23, 2020:

Bill – Thanks for stopping by! Happy Sunday!

Bill De Giulio from Massachusetts on February 23, 2020:

Hi Flourish. Bob Marley came to mind first. There were a few on the list that I didn’t realize we’re from the Caribbean like Rihanna and Nicki Minaj. My generation certainly can’t forget Billy Ocean. Great list, have a great day.

FlourishAnyway (author) from USA on February 20, 2020:

Liz – I’m glad you liked it. Have a great week.

Liz Westwood from UK on February 19, 2020:

The Caribbean has produced some big names in the music industry. You have compiled an interesting list.

FlourishAnyway (author) from USA on February 19, 2020:

MG – Glad you liked this.

FlourishAnyway (author) from USA on February 19, 2020:

Devika – Thanks for stopping by! Have a great week!

FlourishAnyway (author) from USA on February 19, 2020:

Peg – Thank you for your kind comment!

Peg Cole from Northeast of Dallas, Texas on February 18, 2020:

Loved learning about these artists. Surprised by a few that I didn’t know where they originated like Harry Belafonte and Grace Jones.

Devika Primic on February 18, 2020:

I know most of these songs and I enjoyed reading your list of songs. Most of what I did not think of as you have here

MG Singh emge from Singapore on February 18, 2020:

Very exhaustive with a lot of information. liked it.

FlourishAnyway (author) from USA on February 18, 2020:

Heidi – The 80s rock! I wasn’t aware of his given name (Leslie). I would have changed it too, no offense. Thanks for stopping by! I hope you’re doing well.

FlourishAnyway (author) from USA on February 18, 2020:

Linda – Thank you for reading along. I’m glad you were familiar with a few of them.

FlourishAnyway (author) from USA on February 18, 2020:

Audrey – You’re such a sweet lady. Stay warm and have a wonderful week!

Audrey Hunt from Idyllwild Ca. on February 17, 2020:

Question. May I borrow your incredible mind for a while? It just “blows my mind” how you are able to keep this series so interesting and inviting. So much talent evolving from the Caribbean! I’m spending the rest of my evening, relaxing with a cup of hot chocolate to sip on while I treat myself to each of your videos. Marley was the master!

Linda Crampton from British Columbia, Canada on February 17, 2020:

This is an informative article, as usual. I knew three of the artists and enjoy listening to some of their music, but the rest were new to me. It was interesting to learn about them.

Heidi Thorne from Chicago Area on February 17, 2020:

Lots of good coming from the islands! Thought of Billy Ocean right away. Okay, still stuck in the 80s.

Have great week!

Clive Williams from Jamaica on February 17, 2020:

Yeah man….One love!