Later in 1968, and back once more in the United States, Holliday made his Melody Top - Milwaukee Summer Stock Theatre debut in "Fanny" and "Where's Charley". His many lead roles included: Tommy Albright in "Brigadoon", 1973; Carl-Magnus in "A Little Night Music", 1976; Woody Mahoney in "Finian's Rainbow"; Frank Butler in "Annie Get Your Gun" with Jo Anne Worley as Annie, 1982; and Emile De Becque in "South Pacific", 1985. He also appeared many times with the Kenley Players; some of his roles were: as Tony in "West Side Story" with Anna Maria Alberghetti as Maria; as Robert Baker in "Wonderful Town" with Cloris Leachman as Ruth; as Edward Rutledge in "1776" (musical) with Joel Grey as John Adams; as Bill Sikes in "Oliver!" 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.