Tootsie
Dustin Hoffman plays out of work actor Michael Dorsey who tries out for a television role on a whim--only, the part is for a woman. A unique acting challenge is obviously in store when he lands the job, yet this is not the real hurdle for Dorsey.
As his character becomes an overnight success, he contends with a misogynistic director, on top of crushing on a hot co-star (American Horror Story actress Jessica Lange), all the while dressed in drag.
A unique case where comedy and great acting come together, thanks to the direction of Sydney Pollack (he plays Hoffman's agent) and a hilarious script. Seriously though, when was the last time a comedy won an Academy Award for Best Picture?
Signature eighties tropes abound; there's freeze frame, montages, sensual saxophones, and an envelope-pushing PG rating.
A young Bill Murray appears unbilled in a handful of scenes as a roommate.