oh, that would have to be THE KNIFE, which was done during the late 1980s at the Public.
THE KNIFE was a through-composed musical (yes, a musical) by David Hare and Nick Bicat in which the leading male character, played by Mandy Patinkin, undergoes a sex-change operation and becomes a woman, also played by Mandy Patinkin. It was an entirely serious musical without a trace of irony or camp, an apparently sincere but truly awful attempt to say something meaningful about the experiences of a transgendered individual (though the word "transgendered" wasn't in common currency then). As I recall, the show ended with what was intended to be a touching duet between the now-transgendered Mandy Patinkin character and his son, a precocious boy soprano who had come to the cliched realization that Dad still loved him after all. Suffice it to say that the audience was NOT weeping for the right reasons by that point in the show.
This show looked fascinating on paper -- written by Hare, presented by Joe Papp at the Public, given a high-profile cast (Mary Elizabeth Mastrantonio was in it, too) that many composers of musicals would have killed for. However, none of Bicat's music was memorable, Hare's book needed major rewriting, and Mandy Patinkin (a) looked very strange indeed in drag, especially in the absence of any comic intent, and (b) used the upper register of his voice for the "female" songs in a way that was truly unnerving.
Did anyone else out there see this, or were you all still unborn or in elementary school at the time?
"Sweet summer evenings, hot wine and bread /
Sharing your supper, sharing your bed /
Simple joys have a simple voice:
It says why not go ahead?"
