Relatively unknown before the single's release, Shaggy was born Orville Burrell in Jamaica. His music has climbed the European charts faster than that of any other artist. "Oh Carolina" is an old Prince Buster classic and became one of England's biggest radio hits ever. Shaggy was serving in the U.S. Marines at Camp LeJeune, N.C., when he first recorded the song. After active duty in Kuwait during Desert Storm, he returned to the states and tweaked the song, adding his own lyrics and new music.

The single's success in England led Virgin Records to sign Shaggy to a 1.2 million-pound contract, the largest in Virgin's history at the time. Virgin distributed the song all over the globe, including to North America where it topped Canadian charts but saw little success in the United States. During this time, Shaggy also released his first album, Pure Pleasure. Two other singles from the album were released, but compared to "Oh Carolina," the songs were relatively unsuccessful.

Shaggy returned to the charts in 1995 with "Boombastic," another dance-reggae amalgamation that not only topped U.K. charts but U.S. charts as well. The album of the same name was released shortly after, earning Shaggy a Grammy in 1996 for Best Reggae Album. His third album, Midnite Lover, was released in 1997 to mediocre success. In 2000, Shaggy released Hotshot, which fared better than his previous effort. Supported by a tour, Hotshot broke into the Top 25 on Billboard's Top 200 chart.