Before landing a singing career, Steele tried his hand at a number of odd jobs and had a brief spell as a merchant seaman. Like many singers of his era he never did national service, having failed the medical examination because, at eighteen years old, he was diagnosed as suffering with cardiomyopathy. However, according to his autobiography, Bermondsey Boy: Memories of a Forgotten World, he failed the medical because he had flat feet. While on leave or during dock strikes, he played guitar and banjo and sang in the 2i's Coffee Bar and the Cat's Whisker where hand-jiving was devised, two coffee houses in Soho, both as a solo performer and with Wally Whyton's Vipers Skiffle Group. When a ship Steele was serving on docked in Norfolk, Virginia, USA, he heard Buddy Holly and fell in love with rock and roll, turning his back on the British skiffle craze. He was discovered by freelance photographer John Kennedy, who believed Steele could be Britain's answer to Elvis Presley. Later co-manager Larry Parnes was incorrectly credited with creating the stage name 'Tommy Steele.' It was Steele who adapted the surname of his Scandinavian paternal grandfather, Thomas Stil-Hicks (pronounced Steel-Hicks), adding another E to the spelling.