Burrell was born in Kingston, Jamaica. At the age of 18, he and his family moved to the Flatbush area of Brooklyn, New York. In 1987, he took singing courses in Brooklyn and was discovered a year later, while singing in the streets with friends.
Shaggy enlisted in the United States Marine Corps and obtained the MOS of 0811 (field artillery cannon crewman). Shaggy served with a firing battery from the 10th Marine Regiment during the Gulf War. Shaggy perfected his signature singing voice in the Marine Corps and it is also where he got the inspiration for his song "Boombastic".
In January 2010, "Rise Again", a track featuring Sean Paul, Sean Kingston, Alison Hinds, Shontelle Layne, Edwin Yearwood, Destra Garcia, David Rudder, Kees Dieffenthaller, Tessanne Chin, Etana & Belo, was released to support victims of the 2010 Haiti earthquake which struck on January 12. His collaboration with the Balkan group Sahara (consisting of the Romanian singer Costi Ioniţă and the Bulgarian singer Andrea) and French House DJ Bob Sinclar on a track entitled "I Wanna" was a commercial success, released as a single in March 2010 throughout Europe. Shaggy later performed the track several times during Miami's Winter Music Conference in April 2010. In May 2010 he once again performed before cricket audiences at the ICC T20 World Championships, also providing between play performances.
On July 17, 2010, he performed at the Party FM Meja Jam Concert in Country Fair Entertainment Park, Medford, New York. Later that month, he recorded the song "Target" with Japanese reggae singer lecca, which was released on her album, パワーバタフライ (Power Butterfly). Shaggy also released "For Your Eyez Only", which topped reggae charts across the world. Shaggy recorded the song with fellow Jamaican singer Alaine.
In 2011, Shaggy released the official videos of "For Your Eyez Only", along with the hit singles "Sweet Jamaica", featuring Mr.Vegas and Josie Wales and "Girlz Dem Luv We" featuring Mavado. That same year it was announced that Shaggy would release his first new album in four years. Preceded by the single "Champagne", featuring Sahara, the album was released digitally on January 19, 2011. Titled Shaggy & Friends, the album featured many collaborations, including songs with his long-time collaborators Rikrok and Rayvon. A physical release of the album followed. On July 16, 2011, he launched the album Summer in Kingston which contained his single "Sugarcane". The album was launched at a free party in Kingston, Jamaica, where he released the video for "Sugarcane". The video was premiered globally on MTV. "Sugarcane" went on to become the number 2 best selling reggae song on the Canadian iTunes chart, and number 4 in the United States. Shaggy also collaborated with Apache Indian on the latter's album, Home Run, on a remix of "Chokthere".
On January 7, 2012, Shaggy released a collaborative single with Egyptian star Tamer Hosny, "Smile", with a music video filmed in New York City. In February 2012, he re-released his EP, Summer in Kingston, in the form of the Lava Edition, containing two new tracks, one of which was taken from his upcoming Sly & Robbie & Shaggy project, plus a remix of the track "Dame" featuring Kat Deluna.
On April 5, 2012, Shaggy released the lead single from his eleventh studio album, Rise. The track, "World Citizen", is a collaboration with European folk singer Jahcoustix, and was a hit all over Europe. Shaggy launched his own label, Ranch Entertainment, on June 4, 2012, at a press launch in New York City. He was joined by label mates Rayvon and Red Fox for the launch, which was publicized by Manhattan-based PR firm, Fox Fuse and publicist Rhona Fox. Ranch Entertainment is based in New York and Jamaica.
On August 24, Shaggy released his new single, "Girls Just Wanna Have Fun", featuring American female rapper Eve. The song samples the homonymous 1979 hit song by Cyndi Lauper, written by Robert Hazard in 1979 and recorded and released by Cyndi Lauper in 1983. The video for the song was directed by Ras Kassa and released on YouTube on June 14, 2012.
On September 28, Shaggy released Rise across Europe. The album contains nine of the ten tracks from Summer in Kingston, as well as new tracks "Rise", "Girls Just Wanna Have Fun" (the second single), "Diva", "World Citizen" (the first single) and "Get Back My Baby", as well as his single from three years previously, "Fly High".
Shaggy confirmed in January 2012 that he is working on a new studio album, where all of the tracks will be produced by production duo Sly and Robbie. A taster track from the album, "Make Up", featuring Wayne Wonder was released in July 2012, while one of the tracks, "She Gives Me Love", was released early on the Lava edition of Summer in Kingston. In December 2012, Shaggy confirmed that the album would be released in the summer of 2013. On May 14, 2013, Shaggy released the lead single from the album, entitled "Fight This Feeling", featuring Beres Hammond. Shaggy started the year with his first live presentation in Costa Rica on January 20. Shaggy performed live in St. Maarten, Dutch West Indies, on August 23, 2013.
Shaggy is credited for persuading Tessanne Chin to compete in NBC's singing competition The Voice, which she ultimately won.
In 2015 his hit Habibi (I Need Your Love) feat. Mohombi, Faydee & Costi peaked the Billboard Hot 100 and other international charts.