Steele was regarded as Britain's first pop star. Born in London, his cheeky Cockney image, combined with boy-next-door looks, won him success as a singer after starting out as an actor and variety entertainer.
Most of Steele's 1950s hits were covers of American hits, such as "Singin' the Blues". Following the increase in home-grown musical talent during the 1960s, he progressed to a career in stage and film musicals. In the West End he appeared as Hans Christian Andersen. On film, he recreated his stage role in Half A Sixpence, and played character roles in Disney's The Happiest Millionaire and in Finian's Rainbow with Fred Astaire. He also starred in the movie musical Tommy the Toreador, which yielded the hit single "Little White Bull". In 1983 he directed and starred in the West End stage production of Singin' in the Rain.
In 2003, he toured in a production of the musical Scrooge, an adaption of A Christmas Carol.