Circa 2000, Wilson completed work on the film "My Sister's Wedding", which has never been released. He sang "On the Street Where You Live" from "My Fair Lady" for Julie Andrews' awards ceremony when she received the Kennedy Center Honors in 2001. In 2002, his performance as Curly McLain in the Broadway production of "Oklahoma!" received critical acclaim, with Wilson being nominated for the Tony Award for Best Actor in a Musical and the Drama Desk Award for Outstanding Actor in a Musical for the second time each. He won critical acclaim for his performance as the closeted Mormon Republican Joe Pitt in Mike Nichols' 2003 HBO drama miniseries "Angels in America", receiving nominations for both the Golden Globe Award for Best Supporting Actor – Series, Miniseries or Television Film and the Primetime Emmy Award for Outstanding Supporting Actor in a Miniseries or a Movie.