Cliff Richard. Sir Cliff Richard OBE (born Harry Rodger Webb; 14 October 1940) is an English singer who holds both British and Barbadian citizenship. He has sold more than 250 million records worldwide, making him one of the best-selling music artists of all time. He has total sales of over 21.5 million singles in the United Kingdom and is the third-top-selling artist in UK Singles Chart history, behind the Beatles and Elvis Presley.