 1964 saw Holliday in the lead role of Edward Middleton in "The Wayward Way", the musical version of "The Drunkard", at the New Lyric Theatre, Hammersmith; the cast included Roberta D'Esti as Mary, Jim Dale as William Dowton, Cheryl Kennedy as Agnes Dowton, John Gower as the villainous Squire Cribbs, and Bernard Clifton as the landlord and Arden Rencelaw.September 1965 saw him at the Olympia Theatre, Dublin, in the role of Dr Seward, in the musical "Dearest Dracula", with John Gower as Dracula, Mary Millar as Lucy, Robert Hornery as Jonathan Harker, David Morton as Sir Arthur Holmwood, and Pitt Wilkinson as Dr Van Helsing.In 1967, a meeting in New York with Danish actor-director Preben Kaas led to the role of Frank Butler in the Danish version of the musical "Annie Get Your Gun", at the Falconer Theatre in Copenhagen (1967–68), with Daimi Gentle as Annie; this meant an intensive study in phonetics as the role required Holliday singing and speaking in Danish, the success of which can be heard on the Danish Cast recording on Metronome Records HLP 10304 (1968).