Kind Hearts & Coronets, Alec Guinness' tour de force. And I can't believe you missed Tootsie.

Kind Hearst & Coronets! Great call. I included a photo of Tootsie, but you're right -- didn't put it in the list. I'll amend that right now.

In my defense, re: Tootsie, I get a "No hotlinking please" error for the image, so it doesn't show.

And for fans of Ealing comedies, there's also The Belles of St Trinians with Alastair Sim in drag. Then there's The Associate with Whoopie Goldberg. What about movies like Hedwig and the Angry Inch, To Woo Fong.... or Priscilla, Queen of the Desert

I think Silence of the Lambs could count a near gender bending thriller, in that James Gumm is en route to transforming himself into a woman -- a quest that underlies the entire film. While he never completes his transformation, we watch him get closer and closer, including that great scene set to "Goodbye Horses".

Felicity Huffman in Transamerica. My Life As A Dog has a girl who pretends to be a boy in order to be part of a soccer team. La Cage aux Folles / The Birdcage, perhaps, if we include drag queens.

Also, if we are indeed including films with drag queens, then Priscilla, Queen of the Desert and To Wong Foo should be included as well. Both great movies!

Shakespeare in Love comes to mind. As does Albert Nobbs, and based on a true story. There're quite a few other true stories of women living as men from saints to stagecoach drivers that would be fun to tell in film, some possibilities here. For Transporter in the Old West, how about Charley Parkhurst, one of the greatest stagecoach drivers there was, and keeping her identity secret added even more drama to her life.

Juwanna Mann (2002) is another.