In 1956 Holliday went to New York and auditioned for a part in "West Side Story"; he was given the minor role of Glad Hand, and to understudy Tony, in the London production. He then went on to play the lead role of Tony in the West End, during this time he met the young David Jason who was working as an electrician at the time doing work on his London flat and give him tickets to the show. The show also touring England, Scotland and Scandinavia, reprising this role again in 1963 and 1967 at the St. Louis Municipal Opera House. Holliday had two 1966 London Cast recordings to his credit; one with Jill Martin, and the other with Diane Todd, in the role of Maria. He would spend the next ten years commuting between Britain, Europe, the United States, and South Africa where he toured for six months in the role of Macheath in "The Beggar's Opera".