Holgate created the role of the vain opera star Tito Morelli in "Lend Me a Tenor". He was Buffalo Bill Cody in the 1999 revised edition of Annie Get Your Gun starring Bernadette Peters and Tom Wopat, and in the early 2000s he toured as Caldwell B. Cladwell in the first national tour of the musical "Urinetown". Later in 1999, he played Harrison Howell in the Broadway revival of Kiss Me, Kate; as an inside joke, when he made his initial appearance, the orchestra played the intro to "The Lees of Old Virginia," which roused hearty laughter from audience members who remembered his signature role.