He came to prominence in the late 1950s, appearing in the film Expresso Bongo. His boyish good looks and distinctive voice made him an overnight sensation, and a succession of hit records, including Living Doll, were accompanied by a successful film career, in films like The Young Ones (which would give its name to 1980s TV sitcom The Young Ones, in which the characters claimed Cliff as their unlikely role model) and Summer Holiday. He also represented the UK twice in the Eurovision Song Contest, both times unsuccessfully, though his first attempt, Congratulations, was a massive hit in Britain and has become a standard, still sung on suitable occasions.
Most of his early hits were backed by Hank Marvin's band The Shadows, which also had a string of instrumental hits.
During the 1970s, Cliff's popularity with the younger generation waned, but he made a comeback with the number one hit, We don't talk any more. He had become notorious for his conversion to Christianity and his avowed celibate status, being one of the country's most eligible bachelors. Nowadays he tends to be associated with schmaltzy Christmas releases, such as Mistletoe and Wine and Saviour's Day. He reached the pinnacle of his career when he was knighted. He still retains his boyish good looks.
Sir Cliff appears in the 2002 list of 100 Great Britons (sponsored by the BBC and voted for by the public).