Sydney Pollack / Dustin Hoffman - Tootsie

Dustin Hoffman stars in this classic 1980s comedy directed by Sydney Pollack. Michael Dorsey (Hoffman) is an unemployed actor with a reputation for being difficult. Desperate for work, Michael dresses up in drag in an attempt to land a part in a daytime soap as a mature woman. He succeeds, and achieves instant fame as Dorothea Michaels. However, complications develop when he falls in love with Julie (Jessica Lange), a female cast member, while simultaneously having to fend off the amorous advances of both Julies father (Charles Durning) and male actors on the set.