[2][3] Riley grew up in the city's Waterhouse district and attended Kingston Senior School along with Slim Smith.

[4][5] When Smith had success in The Techniques, Riley hung around with the group hoping to join, but was limited to carrying things for them and helping out with harmonies.

[6] On leaving the group in 1967, Riley joined Smith and Lloyd Charmers in the re-formed Uniques, having huge success with songs such as "Watch This Sound" and "My Conversation".

[6] He had several hits in the 1970s, including "Tell The Youths The Truth", "Nyah Bingi", and "Clean up the Streets", and continued to be successful in the 1980s, working with Sly & Robbie's Taxi productions.

[10] In September 2013 he released the album Contradiction, that featured guest appearances from his son Tarrus, Sizzla, and Fantan Mojah.