Little Roy began his career recording a few unsuccessful tracks with producers Coxsone Dodd and Prince Buster. He had his first number one hit with "Bongo Nyah" (1969)for Lloyd Daley ("the Matador"), the first song about the Rastafari movement to be successful commercially in Jamaica. For his song "Don't Cross the Nation" (1970), Little Roy worked with the Wailers and producer Lee "Scratch" Perry. Starting in 1972, Roy worked with Maurice "Scorcher" Jackson and his brother Munchie. Roy recorded the songs "Tribal War" and "Prophecy" in the 1970s. The rhythm from "Prophecy" was used by Steely & Clevie in 1990, leading to a hit record by Freddie McGregor. Roy decided to re-issue some of his old material on an album titled Prophesy. A new album, Live On, was released in 1991, and he worked with Adrian Sherwood on the 1996 album Long Time. Roy released another album in 2005, Children of the Most High.
In May 2011 Little Roy collaborated with Prince Fatty and the Mutant Hi-Fi to record Sliver/Dive cover of Nirvana's early single. An album of Nirvana songs, Battle for Seattle, was released on September 2011 on Ark Recordings.