Tootsie (1982)

When theatrical mastermind Michael Dorsey (Dustin Hoffman) finds himself blacklisted by just about every producer in the acting business, he decides to thwart the entertainment industry by disguising himself as an older woman and auditioning for a daytime soap opera. Dorsey arrives for the audition in a dress and makeup. Calling himself Dorothy Michaels, he/she gives an astonishing screen test and is hired on the spot by the shows executive (Dabney Coleman). Dorsey is an overnight sensation with the shows fans, but as his secret career escalates, his relationship with his girlfriend (Teri Garr) suffers. Soon Dorsey finds a new romantic interest at work with his co-star, Julie. The only problem is, Julie thinks Dorsey is a woman and its not long before shes trying to fix up Dorothy with her single father.

In the tradition of Mel Brooks' THE PRODUCERS, Sydney Pollacks TOOTSIE is a rich, funny, complex film. In featuring Hoffman as the smock-wearing protagonist, its boldness exposes movie-goers to the hilarious challenges faced by a modern cross-dresser. At the same time, the film promoted tolerance for transgendered people. Hoffman is unforgettable as the actor so desperate for work that hell dress as a woman to get it, and supporting players Geena Davis and Bill Murray create plenty of comedy relief to help the plot along.