Pope Joan: there is a musical by Christopher Moore and an opera by John Musto. The ultimate (perhaps) cross-dresser is the possibly mythical woman who became Pope in the middle ages.
There are the "en travesti" roles like Cherubino, Nicklausse, The Composer, and Octavian (among many others), of course, but I think the cross-dressing roles illustrate your theme even more: Leonore in FIDELIO, Zdenka in ARABELLA, Aunt Annie in Beckwith's SHIVAREE, the various Joans of Arc...all women who, for some reason germane to the plot, dress as men in the course of the operas.
17th c. opera star Mlle. Maupin, who enjoyed dressing as a man and duelling.
Queen Christina
George Sand (don't know if anything she wrote was ever set to music) favoured specially-tailored masculine attire. If there's no Sand set to music, perhaps a Chopin song from his "George Sand" period and explanatory programme notes.
Victor/Victoria: A musical all about a male impersonator.
Marlene Dietrich
Saint Eugenia, another holy cross-dresser
In addition to Twelfth Night, Shakespeare's As You Like It also has a cross-dressing theme.
KM ===== My NEIL SHICOFF Website: http://www.radix.net/~dalila/shicoff/shicoff.html
My Website: http://www.radix.net/~dalila/index.html
----- We're sitting in the opera house; We're waiting for the curtain to arise With wonders for our eyes, A feeling of expectancy, A certain kind of ecstasy, Expectancy and ecstasy....Sh's's's.
- Charles Ives
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