Tootsie

Tootsie (1982) is Sydney Pollack's comedy you can watch online on iFILM. Michael Dorsey is a gifted actor nobody in New York will hire — too stubborn, too difficult, impossible on set. So he tries something insane. He puts on a dress, calls himself Dorothy Michaels, and auditions for a soap opera as a woman.

It works. Dorothy lands the role, viewers adore her, and almost overnight she becomes a daytime TV star. The catch: Michael falls hard for his co-star Julie, played by Jessica Lange, who confides in "Dorothy" as a trusted girlfriend and has no clue there's a man behind the wig and lipstick. Every white lie pulls the knot tighter, and the truth keeps getting harder to tell.

Dustin Hoffman spent endless hours in Dorothy's makeup, and the performance turned into one of Hollywood's most quoted. The film won an Academy Award for Lange and drew ten nominations overall, with Bill Murray, Teri Garr and Pollack himself filling out the cast. Stream Tootsie (1982) online on iFILM.