This is based on a 1959 ska song by The Folkes Brothers called "Carolina," which was produced by ska legend Prince Buster. Shaggy incorporated a sample from Henry Mancini's version of "Peter Gunn" into his version.
Shaggy (real name Orville Richard Burrell) was born in Jamaica and moved to America with his parents at the age of 18. At the age of 19 he joined the Marines and spent four years there, earning a commendation from the US government after leading his platoon through a minefield during the Gulf War's Operation Desert Storm. He pursued his music career after returning from Iraq; "Oh Carolina" became his first hit.
This was the first UK hit for the specialist reggae label Greensleves Records despite releasing over 300 records previously.
This went to #1 in the UK after it was used in the Sharon Stone film Sliver.
"Oh Carolina" hit #1 in the UK on March 20, 1993 and stayed there the following week. For both of these weeks, "Informer" by Snow was #1 in America, giving both territories reggae-influenced #1s.
"Sloop John B" is a traditional West Indian folk song, and it was a huge hit for The Beach Boys in 1966. They tweaked the lyric, "This is the worst trip since I've been born" to "...I've ever been on" as a wink to acid culture.
Fall Out Boy's "The Kids Aren't Alright" song title is not a reference to The Offspring's 1998 single of the same name. It actually alludes to The Who's 1979 rockumentary film called The Kids Are Alright.