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 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.

Later in 1968, and back once more in the United States, Holliday made his Melody Top - Milwaukee Summer Stock Theatre debut[3] in "Fanny" and "Where's Charley".

with Vincent Price as Fagin; as Beverly Carlton in The Man Who Came to Dinner with Jack Cassidy as Sheridan Whiteside; as Donald Marshall in Irene with Jane Powell in the lead role; and as Karl in Music in the Air with Giorgio Tozzi as Bruno.

Holliday's other television credits include five episodes - aired in May 1973 - of the long-running British soap-opera Coronation Street, in which he played the character of Tom Schofield, great-nephew of Ena Sharples.