Of the numerous ska-to-rocksteady-era vocalists that transitioned into the role of label-boss and producer, few have had careers as prolific and long-running as the great Winston Riley. In 1962, the teenaged singer began as the leader of the legendary vocal harmony outfit, the Techniques, recording a string of hits for top Jamaican producers such as Coxsone Dodd and Duke Reid. By the early-‘70s, Riley had left the group as a vocalist, focusing instead on production and running his newly-created Techniques imprint. A string of Riley produced hits followed throughout the 1970s, and he eventually scored reggae’s first U.K. pop hit, Dave Barker and Ansel Collins’ funky, piano-driven “Double Barrel.” In the coming decades, Riley continued to write some of reggae’s best-loved riddims; adapting his style for the digital dancehall era, he garnered one of his biggest hits yet with Tenor Saw’s massive “Ring the Alarm,” a ragga-tinged reprise of his own “Stalag 17” riddim.