He decided to pursue his music career and his first hit in 1993: "Oh Carolina", was a dancehall re-make of a ska hit by the Folkes Brothers, which appeared in the film Sliver. The same year, Shaggy appeared on Kenny Dope’s hip hop album The Unreleased Project. He worked together with producers such as Sting International, Don One, Lloyd ‘Spiderman’ Campbell, Robert Livingston and Frankie Cutlass on a remix off his Maxi-Single title “Nice and Lovely”. He had further big hits, including “Boombastic” in 1995, the theme tune of a popular Levi's commercial, and sang with Maxi Priest on his Top 20 hit from 1996 "That Girl".
In 2000, Shaggy released the album Hot Shot, which was certified 6x Platinum in the U.S. The album featured the singles "It Wasn't Me" and "Angel", the latter of which was built around two song samples – Merrilee Rush's 1968 hit "Angel of the Morning" (which was remade in 1981 by Juice Newton), and The Steve Miller Band's 1973 hit "The Joker". The album hit number one on the Billboard 200 and U.K. albums chart. However, his 2002 release Lucky Day, and the 2005 album Clothes Drop, failed to match Hot Shot’s success, although Lucky Day still went gold. The albums, however, found success in Europe, especially with heavy airplay for the single "Hey Sexy Lady". Shaggy remade the Scooby-Doo theme song on the soundtrack titled "Shaggy, Where Are You?". Shaggy also recorded the theme for the 2002 movie Showtime. Shaggy's last top 40 single in the United States was "Angel" from the album Hot Shot.
Following the release of Clothes Drop, Shaggy began to increase his number of live performances. In March 2007, he performed the official song of the ICC Cricket World Cup 2007, titled "The Game of Love and Unity", alongside Bajan entertainer Rupee and Trinidadian soca artist Fay-Ann Lyons, at the opening ceremony of the tournament, held at The Greenfield Stadium, Trelawny, Jamaica. Later that year, he left Universal Music and released his latest album, Intoxication under his own label, Big Yard Records, with distribution rights by VP Records. In August 2007, he joined Cyndi Lauper live on stage in Singapore for the Sonnet Music Festival, where they performed "Girls Just Want to Have Fun" together. In October 2007, he was awarded the Jamaican Order of Distinction for the rank of Commander.
In January 2008, he completed a six-date arena tour with Belgian singer Natalia. He later performed with band En Vogue in Antwerp, to a crowd of 78,000 people. Shaggy also collaborated with Arash in the song "Donya" (Persian: "دنیا"). In April 2008, Shaggy was chosen to record the official anthem for the Mascots (Trix and Flix) of the Euro 2008 football tournament held in Austria and Switzerland. The song, "Feel the Rush", topped charts in most of Europe. In June 2008, a live DVD of his concert material was released under the name Shaggy – Live. In July 2008, he appeared on VH1's "I Love the New Millennium", talking about his video "It Wasn't Me". In August 2008, he performed live at the Dar es salaam festival, to mark the Zain Global Brand launch in Tanzania. The concert was held at the Leaders Club. In December 2008, Intoxication was nominated for Best Reggae Album at the 51st Grammy Awards.
In May 2009, Shaggy performed at the closing ceremony of the 2009 IPL tournament held in South Africa. He also performed at the opening ceremony of the inaugural Champions League Twenty20 in the same month, held in Bangalore, India. In August 2009, he performed live at the Ottawa Reggae Festival in Ottawa, Canada. Here he revealed plans for a new single, "Fading Away", which featured Kevin Rudolf and Lil Jon. He later cancelled this release in favour of "Fly High", a track featuring Gary Pine, which was released on December 5. Shaggy was also invited to perform at the Festival Creole, a festival held every year from November 28 to December 6 in Mauritius.
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. 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.
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