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Mulan strikes me as quite a classic example. It's far removed from comedy, though - the title song, Reflection, brings me out in tears every time. Probably not what you were asking for. ;P

Yentl with Barbra Streisand, Jewish girl dresses and passes as a guy so she can study the Talmud. (I've never seen that movie but seems to be good).

Pope Joan with Johanna Wokalek, she passes as male to become a monk and finally ends up being a pope. (I've watched this movie with my parents, it's somewhat cheasy but the costumes and the medieval Rome scenery is good so watch it on a big screen or not at all)

Both are dramas.

Not a movie, but as a child I was very fond of the historical novels by Thea Beckman. A certain trilogy about the 100 years war between England and France revolved around a girl fleeing from a forced marriage set up by her parents in Bruges. She then lives as a man for safety reasons.

Comedie's, huh?

There's lots of flicks with crossdressing for personal gain.   It's how the "man" keeps us down ..

Tootsie with Dustin Hoffman, though it's old.  Another one is Ms. Doubtfire.   I'm sure if I thought about it longer, I could come up with the titles of at least 2 more that come to mind.

Sorry I have to delete all my posts.

My wife hacked the account.

Please Delete Me.