Monty Phython’s Life of Brian
Shoot. Python’s, even. Also Monty Python’s The Meaning of Life.
But not, as far as I can remember, Monty Python and the Holy Grail. Even though King Arthur does call Dennis “old woman” that one time.
I beg to differ. Terry Jones.
“Who are the Britons?.. Well I didn’t vote for ya.”
Hedwig & The Angry Inch
The silent movie version of “The Wizard of Oz” with a young Oliver Hardy.
I shit you not. Alot of people are listing “man in dress” gags or cross dressers which aren’t exactly the same as transvestites.
This version feautures a Vegas showgirl dance number by a man billed as “Fredrick Kovert” (get it!)
The Fisher King.
all about my mother
I thought cross dresser and transvestite were pretty much synonyms.
I’ve started a thread about this very thing over in IMHO, but I’m too lazy to link. 
For purposes of this thread, any man in a dress will do.
Or, presumably, a woman dressed as a man (see Life of Brian.
Pink Flamingos.
See also, The Year of Living Dangerously.
The Producers
Everything you wanted to know about sex* * but were afraid to ask.
Oddly, the marvellous Divine appeared in “Trouble In Mind” in reverse drag, by which I mean dressed in, of all things, men’s clothes.
You know what’s funny about transvestite movies? Like, where the main character has to wear women’s clothes? And one of the other male characters doesn’t realize it’s really him? And tries to have sex with him?
Damn, that’s funny.
Both Brady Bunch movies.
Midnight in the Garden of Good and Evil
Sulka’s Wedding~ahem~don’t ask :rolleyes:
Transvestites take it a step further by emulating a woman’s mannerims.
Compare Maxwell Q. Klinger of “MAS*H” with Dr. Frank-N-Furter of Rocky Horror. Frank is proud to be called a transvestite (he even sings about it) whereas if you called Klinger that he’d probably slug you–he’s just trying to get out of the Army.