He sought out many producers while still going to school, trying to get his songs recorded without success. He also entered talent contests. "One night I was walking past a record store and restaurant as they were closing, pushed myself in and convinced one of them, Leslie Kong, to go into the recording business, starting with me," he writes in his own website biography.
After two singles that failed to make much impression, his career took off when his "Hurricane Hattie" became a hit, while he was aged 14. It was produced by Kong, with whom Cliff remained until Kong's death from a heart attack in 1971. Cliff's later local hit singles included "King of Kings," "Dearest Beverley," "Miss Jamaica," and "Pride and Passion." In 1964, Cliff was chosen as one of the Jamaican representatives at the World's Fair and Cliff soon signed to Island Records and moved to the UK. Island Records initially (and unsuccessfully) tried to sell Cliff to the rock audience, but his career took off in the late 1960s.His international debut album was Hard Road to Travel, which received excellent reviews and included "Waterfall" (composed by Nirvana's Alex Spyropoulos and Patrick Campbell-Lyons), which became a hit in Brazil and won the International Song Festival.
"Waterfall" was followed in 1969 by "Wonderful World, Beautiful People" and "Vietnam" in 1970, both popular throughout most of the world. Bob Dylan called "Vietnam" the best protest song he had ever heard.Also during this period, Cliff released a cover of Cat Stevens' "Wild World" as a single, but it was not included on his Wonderful World, Beautiful People album.http://youtu.be/b4V9AYhtKkg