Head began acting and writing songs as a child, and by the mid-1960s had a London recording contract. He had limited success until selected by Tim Rice and Andrew Lloyd Webber to play Judas Iscariot on the original album version of Jesus Christ Superstar. At around the same time he won a leading role in the Oscar-winning Sunday Bloody Sunday (1971), alongside Peter Finch and Glenda Jackson. Despite these successes, he received little public attention in the next ten years, reappearing in the spotlight in 1984 as the star of the musical, Chess. The song "One Night in Bangkok," from Chess, featuring Head on lead vocal, became a radio hit.