Tootsie (1982)

The classic comedy Tootsie (1982) features Dustin Hoffman as Michael Dorsey, an unemployed NY actor that is having a hard time finding work, mainly because he has a history of being difficult to work with. After many months without a job, Michael’s friend Sandy Lester (Teri Garr) tips him off that a soap opera is looking to fill a role as a female hospital administrator. With nothing left to lose, Michael dresses up as a gal and scores the role as “Dorothy Michaels”. It’s only a matter of time before the cross-dressing dude starts adopting his female persona outside of the movie set. Dorothy/Michael’s dress-wearing lifestyle eventually crimps his love life when he begins crushing on his co-star Julie Nichols (Jessica Lange), a single mother wasting away in an unhealthy relationship with the soap’s director, Ron Carlisle (Dabney Coleman). Things get really complicated when Julie starts developing feelings for Dorothy. You’ll develop strong feelings for Hoffman when he gets caught with his dress off, wearing some tight black briefs. Mr. Hoffman will turn you into Mr. Jerk-Off man!