Jack Lemon & Tony Curtis in "Some Like It Hot"
Dustin Hoffman as "Tootsie"
Robin Williams as "Mrs Doubtfire"
Martin Lawrence as Big Momma in "Big Momma's House" and he liked it so much he did a sequel.
"To Wong Foo, Thanks for Everything... Julie Newmar"
"Glen or Glenda"
Johnny Depp as "Ed Wood", and of course Ed Wood...
Tom Hanks in the "Bosom Buddies" TV series
Anthony Perkins as "Mother" in "Psycho"
Willem Dafoe in "Boondock Saints"
"Viktor und Viktoria" (1933) and subsequently Julie Andrews' version...
And before all that, of course... There's a whole lotta shakin' goin' on in
Shakespeare ... "Twelfth Night", "As You Like It", "Merchant of Venice" etc...
Pecunni's "Madama Butterfly"
"Kiss of the Spider"
"The Crying Game"
"Hedwig & The Angry Inch"
"Short Bus"
"Adventures of Priscilla Queen of the Desert"
"Rocky Horror Picture Show" was already mentioned, so I won't mention it. Oops, I mentioned it.
"Bird Cage"
As with Shakespeare's bi-directional cross-dressing characters, here's some for the ladies:
"Mulan"
"Joan of Arc"
Gwyneth Paltrow in "Shakespeare In Love"
"Les Miserables"
"Orlando"
Cate Blanchett as Bob Dylan
Angelina Jolie as male Russian in "Salt"
Mary Pickford as Cedric Errol in the 1921 film "Little Lord Fauntleroy"
That's all mostly off the top of my head. Mostly. I had to search online for a few things to joggle my memory and doing so joggled a few more I'd forgotten about such as "Boondock Saints" and "Birdcage"
From aforementioned search, a few surprises I didn't catch oh so long ago: David Duchovny in "Twin Peaks"
Arnold Scharznoogie in "Junior", which I've never seen.
Couldn't remember her name, nor the movie, but I remember seeing it and my dad saying the character was played by a woman... FINALLY found it:
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My dad made the comment 'cause I said that guy sure is a good actor.
"Actress"
AND she won an Academy Award for that role.
Plenty more movies/plays I haven't seen or don't recall but as everybody knows — it's all online...
Really, I don't see what the big deal is. Cross dressing has been going on since before men & women wore different clothes – it's only after the gender-specific attire came into vogue that some have titillated others/and or themselves with their sartorial gender-bender antics.
...
FWIW: 9 yards of pleated, thick wool is probably not the most practical stage attire.
[Scottish Brogue]Aye, and hence the orrrrigin of th' phrrrrase "The whole nyne yarrrrrds", lad. (As I'm shooorrrr yee knew alrrrrreadeh)[/Scottish Brogue]