I don't know if the movie co-starring Jack Nicholson opened in 2003, or never opened at all...let's just take a look at how a very average looking guy LONGS to put on a wig and a dress and be a hooker! 
In this indie movie, three guys played three women...but didn't play drag queens or acknowledge they were men. It was the story of Evie, a sagging actress (played with a bit too much Phyllis Diller by Jack Plotnick) who bitches at her live-in friend Coco (Clinton Leupp) before the arrival of breathy and busty Varla (Jeffery Roberson) who is the daughter of a former rival of Evie's The campy comedy-drama has some good catty lines, and tries to avoid stepping into John Waters' tasteless territory or too overt camp....and isn't bad at all. Many critics found the lead actors fairly revolting and unconvincing as women, but Clinton's "Coco" had some nice moments, and Roberson was generally considered the only one who wasn't "a drag."
Runner up, just for weirdness, is WOODY HARRELSON!
I don't know if the movie co-starring Jack Nicholson opened in 2003, or never opened at all...let's just take a look at how a very average looking guy LONGS to put on a wig and a dress and be a hooker!
And here's a very cute moment. Our fascinatiion with lace unmentionables and pretty lingerie means that once we put them on....
we've just GOT to admire ourselves! Oooh! Ooooh! How sweet!
AND MORE RUNNERS-UP....Ooof, it's Kelly Ripa and Regis Philbin, and their bodies may have been in it, but not their hearts....
News Item of 2003: February, in Deptford High School in New Jersey, two male students were handed detention for coming to class in skirts. Jim Harner was one of them, and he declared that the school was guilty of "discrimination based on gender. Girls can wear pants and skirts. Equality of the sexes should work both ways."
You go, girl. Uh, guy. Women don't like to wear cumbersome pants all the time, and shorts are equally restrictive. We ALL know this. How many guys come out of the shower and make a "skirt" out of the towel around the waist? Comfortable, isn't it! 'Nuff said....