Tootsie (1982)

Forty years ago, Sydney Pollack directed one of the most acclaimed and most successful comedies of all time with this gender-bending sorta-romantic comedy starring Dustin Hoffman as Michael Dorsey. Dorsey is an unemployed actor who suddenly finds success disguised as Dorothy Michaels, a suddenly successful actress who becomes of the leads of a popular daytime soap opera. Jessica Lange plays Julie, her co-star whom Michael falls in love with, Charles Durning plays Julie's father Le...