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Dean Webb was born Michael Eaton in Reading, Berkshire, in 1940 and was educated at St. Annes Roman Catholic School in Caversham. Before becoming a singer, he was, for a while, an apprentice blacksmith in Reading town centre. On embarking on a singing career, he changed his name, basing his surname on Cliff Richard's real name. In 1959 he made a couple of records for Parlophone and appeared on Jack Good's Oh Boy! TV show, but didn't manage any lasting success. He was on the same bill as Eddie Cochran and Gene Vincent when Cochran was tragically killed in a road accident near Bath in 1960. He also made a couple of small acting appearances on film and TV in the early sixties.