Her name was Lola
Classy cross-dressing films in no order:
Before Night Falls - Okay, the movie isn't that great, but its worth seeing for one reason: Johnny Depp. He plays two roles and the more remarkable of the two is the hottest piece of cross-dressing ass you are likely to find in any Cuban prison.
Hedwig and the Angry Inch - Wonderful on so many genderfuck levels. Yitzhak is played by a woman, playing a man who used to be a drag queen. ??? Exactly. And of course there is Hedwig, and his botched sex change which left him neither/both sexes. It's a great movie and John Cameron Mitchell looks amazing as Hedwig.
Rocky Horror Picture Show - Of course. Not my favorite, but it is a classic.
Some Like It Hot - One of my all time favorite movies and although it was made in '59, the comedy endures. Tony Curtis and Jack Lemmon cross dressing as ugly women to get work, escape the mob, and find marriage partners = awesome.
Pink Flamingos (or anything with Divine in it, preferably directed by John Waters) - "I am the filthiest person alive!" This movie is so amazingly bad it's good. Really really good.
Boys Don't Cry - Oh yes, cross dressing can go both ways. Tragic.
Osama - Girl cross dressing to stay alive and trying to remain undiscovered by the Taliban. Even more tragic.
Crying Game - A staple and still terrifying straight men everywhere.
Tootsie - Dustin Hoffman is so ugly its believable.
Bird Cage - My goodness Gene Hackman is an ugly woman.
Morocco - Marlene Dietrich in this 1930 film dresses in a tuxedo, sings a lusty song, seduces the crowd, kisses a chick and makes Gary Cooper her "girlfriend." Actually you know what? Anything she has ever been in counts. Did you know she showed up to a film premiere in a tux? This is when women didn't wear pants, forget about men's formal wear. Paramount thought it was great publicity at first, suit companies wanted her to advertise for them and whatnot. She told them off, said she just felt comfortable in men's clothes and wouldn't sell suits or the idea of menswear to women. Then there was backlash and Paramount hushed the whole thing up since Marlene turned out to be a bit "controversial." But I digress.
Psycho - Introducing the masses to the word 'transvestite.'
I Was a Male War Bride - Cary Grant cross dressing to get out of the army.
Not cross-dressing, but related:
Southern Comfort - This is one of the most remarkable documentaries I have ever seen. Just see it. It's about transgendered people, and above all else (this sounds bad) it made me see that they are people. Not freaks, not weirdos, not people so far removed from your existance that you can't identify with them in anything beyond abstract thought (like oh, I guess they eat, breathe, sleep... so we have that in common). Here are people with families, with children, with spouses, with jobs, with hopes and fears and dreams just like everyone else. I have to tell you, it made me cry, and that is something I don't do. Now that is a good movie.
Before Night Falls - Okay, the movie isn't that great, but its worth seeing for one reason: Johnny Depp. He plays two roles and the more remarkable of the two is the hottest piece of cross-dressing ass you are likely to find in any Cuban prison.
Hedwig and the Angry Inch - Wonderful on so many genderfuck levels. Yitzhak is played by a woman, playing a man who used to be a drag queen. ??? Exactly. And of course there is Hedwig, and his botched sex change which left him neither/both sexes. It's a great movie and John Cameron Mitchell looks amazing as Hedwig.
Rocky Horror Picture Show - Of course. Not my favorite, but it is a classic.
Some Like It Hot - One of my all time favorite movies and although it was made in '59, the comedy endures. Tony Curtis and Jack Lemmon cross dressing as ugly women to get work, escape the mob, and find marriage partners = awesome.
Pink Flamingos (or anything with Divine in it, preferably directed by John Waters) - "I am the filthiest person alive!" This movie is so amazingly bad it's good. Really really good.
Boys Don't Cry - Oh yes, cross dressing can go both ways. Tragic.
Osama - Girl cross dressing to stay alive and trying to remain undiscovered by the Taliban. Even more tragic.
Crying Game - A staple and still terrifying straight men everywhere.
Tootsie - Dustin Hoffman is so ugly its believable.
Bird Cage - My goodness Gene Hackman is an ugly woman.
Morocco - Marlene Dietrich in this 1930 film dresses in a tuxedo, sings a lusty song, seduces the crowd, kisses a chick and makes Gary Cooper her "girlfriend." Actually you know what? Anything she has ever been in counts. Did you know she showed up to a film premiere in a tux? This is when women didn't wear pants, forget about men's formal wear. Paramount thought it was great publicity at first, suit companies wanted her to advertise for them and whatnot. She told them off, said she just felt comfortable in men's clothes and wouldn't sell suits or the idea of menswear to women. Then there was backlash and Paramount hushed the whole thing up since Marlene turned out to be a bit "controversial." But I digress.
Psycho - Introducing the masses to the word 'transvestite.'
I Was a Male War Bride - Cary Grant cross dressing to get out of the army.
Not cross-dressing, but related:
Southern Comfort - This is one of the most remarkable documentaries I have ever seen. Just see it. It's about transgendered people, and above all else (this sounds bad) it made me see that they are people. Not freaks, not weirdos, not people so far removed from your existance that you can't identify with them in anything beyond abstract thought (like oh, I guess they eat, breathe, sleep... so we have that in common). Here are people with families, with children, with spouses, with jobs, with hopes and fears and dreams just like everyone else. I have to tell you, it made me cry, and that is something I don't do. Now that is a good movie.