 At the age of twenty-six, in 1998, he starred in his first off-Broadway show, the controversial "Corpus Christi" by acclaimed playwright Terrence McNally.In the same year, he also appeared in "The Matchmaker" by Williamstown Theatre Festival, as well as an off-Broadway staging of "The Cripple of Inishmaan".During the following year, Fitzgerald appeared in the Sondheim-Weidman musical "Wise Guys".