Mrs. Doubtfire

It seems like that insane things are acceptable when it's in the name of family, and that's certainly the case for "Mrs. Doubtfire." Robin Williams stars as a guy who hits the sad streak of losing his job and getting divorced (both for petty reasons IMO).  In order to spend more time with his children, who his ex-wife is too busy to properly care for but the court decreed he could only see them on one day a week, he takes the role of going undercover as an elderly English nanny.  Just in time too because his wife starts to see a new beau that looks suspiciously like James Bond.  Beyond the whole "father learns to love his family more" trope, the main reason to watch is to see when it'll all go south.  There are so many close calls with his cover getting blown, that eventually, all you want to know is how long he can keep up the facade.  The ending itself is surprisingly bittersweet, but it's a better turn from the cliche happy ending of the couple getting back together.  Robin Williams is at his comedic best, doing a variety of voices and mannerisms that define his fame. Despite his cover of a real supernanny, what with him NOT being one, his goof-ups are hilarious as well.
Overall, nutty fun involving Robin Williams pretending to be a woman with a small sappy center of going to the extreme for your family.

Let's recap:

Wholesome Crossdresser

vs.

Crossdressing for the lulz

Androgynous

MEN SHOULD NOT LOOK LIKE THIS!