Deriving his name, and to some extent his style, from U-Roy, Reid was also heavily influenced in his early career by Dennis Alcapone. With early recordings for Gussie Clarke, Glen Brown, Lee Perry and Bunny Lee, Reid established himself at the forefront of 1970s reggae DJ"son His debut album Presenting I Roy is considered a classic of its genre, and was followed up by a series of strong albums including Hell and Sorrow.
Linton Kwesi Johnson dubs I-Roy "the mighty poet" in "Street 66" on the album, Bass Culture:
The mighty poet I-Roy was on the wireWestern did a skank.
And each man laughan feelin Irie. Dread I;Street 66, the said man saidany policeman come erewill get some righteous ras klaat licksyeah man - whole heap kicks.
In 1976, I-Roy signed to Virgin Records with whom he released five albums. On occasion he would utilise the Revolutionaries as his backing band.
One of I-Roy"s earliest hits was in 1972 with "Sidewalk Killer," a take on Tommy McCook"s original "Sidewalk Doctor." This 45 was produced by Ruddy Redwood.
Reggae"s move to the dancehall era in the 1980s saw I-Roy"s popularity decline. This decline in popularity and recurring health problems led to periods of homelessness during the later period of his life. He died in 1999 of heart failure, at the age of fifty-five.