He moved to Chicago to live with his aunt, and tried unsuccessfully to break into show business while still in high school. During World War II, he lied about his age to join the Coast Guard. After the war, he assumed the stage name of Tony Fontane and moved to New York City, looking for work as a singer, but did not have much success. He finally landed a spot on the Major Bowes Original Amateur Hour, which he won. Fontane became an instant sensation; according to his biography, "A Bargain With God," he was one of only two performers on the Amateur Hour to ever be called back for an encore – the first being Frank Sinatra.