One of my all-time favorites!
Sydney Pollack's "Tootsie" stars Dustin Hoffman as the consummate out-of-work actor: He's constantly complaining about the lack of jobs and yet every time he lands a part, he loses it, burns a bridge or somehow alienates the director/cast/crew by being ridiculously difficult (in service of the part of course!).
Tootsie is both a send-up of the reputation of the "difficult" actor as well as a telling portrayal of gender stereotypes.
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-- @misterbowen