The Kids in the Hall played various female characters in their movie “Brain Candy” (e.g. Bruce McCulloch as Alice, Scott Thompson as Mrs. Hurdicure) .
And then there’s Divine…
I think that many (not all) of Ru Paul’s film appearances can qualify, such as playing Mrs. Cummings in The Brady Bunch Movie (1995)
Doesn’t count. Tony Curtis plays a guy who disguises himself as a woman.
(Ditto for Jack Lemmon in the same film)
But nobody’s perfect.
Arsenio Hall as “Extremely Ugly Girl” in Coming to America.
The original hologram of the Emperor in Empire Strikes Back was a woman (Marjorie Eaton) with chimp eyes.
And Terry Jones as Brian’s mother in Life of Brian.
There are the many times Peter Pan was played by a woman, beginning with Betty Bronson in the 1924 silent version. Mary Martin played Pan in the first adaptation I saw, although that was on TV, not in the movies. She played the role onstage, as did Mary Lou Retton, Sandy Duncan, and Cathy Rigby.
If animation counts, Bart Simpson is voiced by a woman (Nancy Cartwright).
Would dr. Liet Kynes in Dune count?
Terry Jones played female roles in Monty Python’s Life of Brian and (lesser so) in The Holy Grail. Jones, Gilliam and Idle played women in Meaning of Life.
If you’re talking about the most recent adaptation, then no – they changed the sex of the character for that movie. Sharon Duncan-Brewster wasn’t playing outside her sex.
Lassie
Debra Winger (uncredited) as “Emmet” in Made in Heaven (1987).
Tyler Perry doesn’t appear in the Big Momma movies; that’s Martin Lawrence, and Big Momma doesn’t count for this because she is the undercover identity of male FBI agent Malcolm Turner.
Do Juno and other movies starring a transgender person pre-transition count?
Meryl Streep as the Rabbi in Angels in America. She was so impeccable that I had no idea that 1. it was a woman and 2. it was Meryl Streep, until I watched the credits.
I was wondering that myself. I guess Elliot Page identified as a woman back than, as far as I know?
Damn - I was thinking of the Madea movies.
You could say the Talosians in the Star Trek pilot The Cage fit the bill. Women played the Talosians, I suspect for reasons similar to The Old Dark House – they wanted a slimmer appearance and a high-pitched voice which, along with the bulbous head makeup, made them seem pretty alien.
On the other hand
1.) We only assume the aliens are “really” male because of our 1960s cultural preconceptions
2.) Who says the Talosians were male? Maybe they were female all along.
3.) They’re alien -0- who says that they even have two sexes, or that their sexual characteristics resemble those of humans at all.
In addition to your other points, that was also a TV show, not a movie.