gender-bending: disguises from pre-1980

Perfect Gentlemen
The Million Dollar Ripoff
Return of the Pink Panther
Theatre of Blood

Gender-bending: Male disguises of the 1970s & earlier

From Shakespeare to Shakespeare in Love, playwrights and filmmakers have delighted in disguising their female characters as men. Sometimes they have aimed for a realistic look and sometimes they’ve played it for laughs.

Then, of course, there are the actresses who have played male characters or cross-dressing characters.