From ‘60s reggae legends to dancehall superstars of the ‘00s, this list will introduce you to the most influential Jamaican singers of all time.
Jamaica may be a small island, but its influence on music around the world is enormous. The home of reggae, roots, rocksteady, dub, ska, and dancehall, Jamaica has spawned its fair share of musical legends, including songwriters, record producers, and singers.
Let’s take a look at some of the most iconic Jamaican singers that everyone should know.
Sister Nancy
Sister Nancy is a singer who should be on every music lover’s radar. She is also probably the most famous female Jamaican singer in the world, thanks to her infectious 1982 hit ‘Bam Bam’ which went on to become an internationally-adored reggae classic.
At the start of her career, she was known as the first female dancehall DJ. She went on to release three albums – One, Two (1982), The Yellow, The Purple & The Nancy (1982) with fellow Jamaican singers Yellowman, Fathead, and Purpleman, and Sister Nancy Meets Fireproof (2001).Â
In comparison with some of the artists on this list, Sister Nancy is by no means prolific. But that does not make her contribution to music any less significant. In 2021 she made a return with her Armageddon EP, which is well worth a listen.
Peter Tosh
Peter Tosh is one of the biggest names in Jamaican music, partly thanks to being a core member of The Wailers, but also as a solo artist. A guitarist and singer, Tosh was one of the three founding members of The Wailers in 1963 along with Bob Marley and Bunny Wailer.Â
Tosh began releasing solo projects in 1976, releasing seven albums over the next decade. His 1976 album Legalize It and his 1977 album Equal Rights are his best known.
 His biggest hit was ‘Get Up, Stand Up,’ a song that he co-wrote with Bob Marley. His other hits include ‘Stepping Razor’ and ‘Legalize It.’Â
Tosh was tragically murdered during a robbery at his home in Jamaica in 1987. To this day, Tosh is revered worldwide as one of reggae music’s most important figures.
Lee ‘Scratch’ Perry
Lee ‘Scratch’ Perry was a Jamaican singer and producer who was a pioneer in dub music. He is without a doubt one of the biggest names in Jamaican music for this reason.
Dub music began with producers like Perry sampling existing reggae tracks, removing the vocals, and emphasising ‘riddim’ or rhythmic aspects of the track. In this respect, dub producers like Perry lay the foundation for all electronic music.
Although he is known first and foremost for his contribution to dub, Lee Perry was also a singer, and his voice features on a number of tracks. He released over sixty albums in his career – a staggering number. Some of his hits include ‘I Am The Upsetter’ and his version of Max Romeo’s ‘Chase The Devil.’
Desmond Dekker
Desmond Dekker was a Jamaican singer known for ska, rocksteady, and reggae music. Along with his band The Aces, Desmond Dekker is recognised as one of the most important Jamaican artists in bringing reggae to a global audience.Â
His 1968 hit ‘Israelites’ reached the top ten in charts all over the world. Other hits included his 1967 single ‘007 (Shanty Town)’ and his 1970 single, ‘You Can Get It If You Really Want.’
Aside from his own musical success, Dekker is credited for discovering Bob Marley and bringing him to the attention of Lesley Kong’s record label, Beverley’s. Dekker’s international success also helped lay the foundation for Bob Marley’s music to take the world by storm.
Dekker moved permanently to the UK in 1969. In a tragic twist of fate, Dekker was declared bankrupt in 1984. He died suddenly of a heart attack at home in London in 2006.
Bunny Wailer
Bunny Wailer was one of the founding members of The Wailers, along with Bob Marley and Peter Tosh. A singer and a percussionist, he also had several big releases as a solo artist on which he often collaborated with legendary Jamaican session musicians Sly and Robbie.
Bunny took inspiration from a range of genres, with gospel and soul influences coming through in his singing. His 1982 album Hook Line & Sinker even touches on elements of disco.
His debut solo album Blackheart Man (1976) is probably his most critically-acclaimed, with many regarding it as an album that represents the height of the golden era of reggae music.
Like the rest of the Wailers, Bunny was a committed Rastafari, and towards the end of his career he declined shows that he felt went against his spiritual principles.
It would be fair to say that Bunny Wailer is widely regarded as one of the great Jamaican singers of the twentieth century.
Toots Hibbert
Toots Hibbert was a Jamaican singer and songwriter best known as the singer of Toots and the Maytals. He is regarded as a pioneer of reggae music, with his defining 1968 song ‘Do the Reggay’ being the first song to use the word ‘reggae.’
A seminal figure in reggae music in the ‘60s, his most commercially successful album actually came in 2004 in the form of True Love. The album saw Toots & the Maytals re-record some of their greatest hits along with special guests. It charted at number two in the Billboard reggae album charts, and won the 2005 Grammy Award for Best Reggae Album.
Toots’ enduring hit is the 1973 reggae classic ‘54-46 Was My Number.’ Other hits from the artist include ‘Pressure Drop’ and ‘Funky Kingston.’ Toots died in Kingston, Jamaica in 2020.
Vybz Kartel
Vybz Kartel is a Jamaican singer and producer, working predominantly in dancehall and reggae music. He has collaborated with a number of US hip-hop and R&B artists, including Jay-Z, Rhianna, and Major Lazer. Drake has cited Vybz Kartel as one of his ‘biggest inspirations.’
Vybz has been at the centre of a great deal of controversy in Jamaica. In the 00s, a feud broke out between Vybz Kartel and his former collaborator, fellow Jamaican dancehall singer Mavado, after Vybz left the dancehall collective, The Alliance. The artists released various ‘diss’ tracks, with Jamaican youth jumping onboard different sides of the faction, with the feud spilling into street violence.
In 2014, Vybz was sentenced to life imprisonment for the murder of Clive ‘Lizard’ Williams. He continues to release music from prison.Â
His most successful album is his 2016 King of the Dancehall, which peaked at number two on Billboard’s reggae albums chart. Vybz’s hits include ‘Summertime,’ and ‘Fever’ which became certified Gold in 2020.
Sean Paul
Sean Paul is a Jamaican singer and rapper, and one of the most prolific and successful dancehall artists in the world today. He has topped the Billboard Hot 100 chart twice, with his singles ‘Get Busy’ (2003) and ‘Temperature’ (2005).Â
Sean Paul has featured on a number of other hit tracks, including Beyoncé’s chart-topping 2003 single, ‘Baby Boy.’
Since dropping his debut album Stage One in 2000, several of Sean Paul’s eight albums have been nominated for the Grammy award for Best Reggae Album, with his 2002 Dutty Rock winning the award in 2004.
After two decades of success, Sean Paul has stated that he intends to continue his music career. He has cited Toots Hibbert as an inspiration, saying ‘he’s up there in years and he’s doing it. Those kind of artists inspire me. I know I’m just going to keep on doing music as long as I can.’
Shaggy
Shaggy is a Jamaican-American singer who achieved phenomenal success in the ‘90s and ‘00s especially with his reggae-influenced pop hits ‘Boombastic,’ ‘It Wasn’t Me,’ and ‘Angel’ amongst others.Â
His 1995 single ‘Boombastic’ was his first major success, peaking at number three on the Billboard Hot 100. In 2000, Shaggy’s success hit new levels with his hit songs ‘It Wasn’t Me’ and ‘Angel,’ both of which were certified triple platinum, topping the Billboard Hot 100, and charts around the world.
He has released sixteen studio albums since 1993. Six of his albums were nominated for the Grammy award for Best Reggae Album, with Boombastic (1996) and 44/876 (2019) – a collaborative album with Sting – winning the award.
His philanthropic project Shaggy and Friends has supported the Bustamante Children’s Hospital in Kingston, Jamaica. Shaggy undeniably sits amongst the great Jamaican singers of the twenty-first century.
Damian Marley
Out of Bob Marley’s offspring, Damian Marley has arguably achieved the greatest musical success. Damian is nicknamed ‘Junior Gong’ after his father, who was known as ‘Tuff Gong.’ His biggest hit is his 2005 single, ‘Welcome to Jamrock.’
Beginning his performing career at the age of thirteen, Damian Marley has released four solo studio albums, with the 2005 album Welcome to Jamrock being the most successful, with a Gold certification. The album peaked at number seven on the Billboard 200 album chart, and topped Billboard’s reggae album chart.
Damian’s 2010 collaborative album with Nas, Distant Relatives, was another major success, with the record topping both Billboard’s rap and reggae album charts, as well as reaching number five on the Billboard 200 album chart.
Damian’s older brother Stephen very much shares in Damian’s success, as the revered producer of Damian’s albums Halfway Tree and Welcome to Jamrock.Â
While Damian has amassed an impressive four Grammy awards, Stephen has an incredible eight Grammys to his name. However, with Stephen more often working in the background, and Damian more often taking to the stage as a singer and frontman, Damian is generally the more recognised name.
Jimmy Cliff
Jimmy Cliff is one of the most revered and most prolific Jamaican singers of the twentieth century. With his music touching on ska, rocksteady, and reggae, Cliff is credited as one of the key figures who helped bring reggae to a global audience.Â
Alongside his musical releases, Cliff starred in the 1972 film The Harder They Come – a crime film which has been described as the most influential Jamaican film of all time, and whose reggae soundtrack proved hugely popular.
Cliff has released over thirty studio albums. The most successful of his albums include The Harder They Come (1972), The Power and the Glory (1983), and Higher and Higher (1996), the latter two of which were certified Gold.
Cliff’s music career has spanned a stunning seven decades, with his most recent album Refugees coming out in 2022.
Burning Spear
Burning Spear is a roots reggae singer and songwriter, and is widely considered to be one of the most enduring roots reggae artists of his time. His music is heavily influenced by his Rastafari beliefs.
Despite beginning his musical career in the ‘70s, Burning Spear has found continued success well into the twenty-first century. Both his 1999 album Calling Rastafari, and his 2008 album Jah Is Real were awarded the Grammy award for Best Reggae Album.
Since the ‘70s, Burning Spear has released a total of twenty-eight studio albums. His biggest hits include ‘Marcus Garvey’ and ‘Slavery Days.’
Spice
Recognised universally as the ‘Queen of Dancehall,’ Spice is probably the most famous female Jamaican singer and recording artist in the world. Her first success came with her 2009 single ‘Romping Shop’ with Vybz Kartel. Her 2018 mixtape Captured shot to the top of the Billboard reggae albums chart.
Spice ascended to new levels of success coming out of the pandemic. Her long-awaited debut album 10 (2021) was nominated for the Grammy award for Best Reggae Album. This was shortly followed by her second album, Emancipated (2022). Â
Her biggest hits include ‘So Mi Like It’ and ‘Go Down Deh’ featuring fellow Jamaican singers, Shaggy and Sean Paul.
Bob Marley
Bob Marley is universally recognised as the most influential Jamaican singer of all time, as well as one of the twentieth-century’s greatest songwriters.Â
Pioneering the genre of reggae, Bob Marley is internationally revered as a Rastafari icon, and is known around the world for both his music and the political views he represented. He is undoubtedly the most successful reggae artist of all time.
Along with his band, The Wailers, Bob Marley released thirteen studio albums between 1965 and 1983. A number of these albums were Gold certified, with Kaya (1978) becoming Platinum certified. But Marley’s contribution to music can hardly be summarised in terms of chart success. His legacy and influence clearly transcends the standard popularity metrics of the music industry.
The 15x Platinum posthumously released 1984 album Legend is the perfect introduction to Bob Marley’s music. It features many of his most loved songs, including, ‘No Woman No Cry,’ ‘Could You Be Loved,’ ‘Three Little Birds.’ ‘Is This Love,’ ‘Jamming,’ ‘Buffalo Soldier,’ ‘Waiting In Vain,’ ‘Redemption Song,’ and ‘Sun Is Shining.’
Bob Marley died tragically on 11 May 1981, aged 36. His music and his legacy lives on.
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