Tootsie (1982)

This is a great film and quite hilarious.
Michael Dorsey (Dustin Hoffman) is an opinionated character actor who is struggling to find work in New York City. He is determined to gather $8,000 to produce his roommate's weird play, but he is impossible to work with, trying to tell the directors what his character should be doing. Suddenly, he gets a great idea, he disguises himself as a woman, Dorothy Michaels, and auditions for the role of a woman in a soap opera, getting the part after fighting the director over it, determined not to be put down because he is a woman. So he gets the role of the woman doctor.
He can't believe all the crap women must deal with and he moans to his roommate, Jeff (Bill Murray, great) about not having a good handbag because women are animals in the shopping malls. Though Jeff knows his big secret, Sandy (Teri Garr). It will kill her if she knew the truth. She literally gets suicidal at a birthday party. Instead, they just tell her that a relative died. Sandy does not react well to the actress who plays the role and though Michael is convinced that he is being strong but Sandy believes him to be weak as Emily. However, his disguise creates a problem: Julie Nichols (an Oscar-winning Jessica Lange) who plays a nurse in the soap. She is also a single mother with a widowed father, Les (Charles Durning), but she is sleeping with the sexist director (Dabney Coleman). Plus, she thinks (naturally) that Dorothy is a woman. Julie is honest but must have a low opinion of herself for she even admits that she always picks the worst guy for her.
The film plays out with a various amount of problems, including Julie's father developing a crush on Dorothy and the two of them having an odd sort of relationship. He even goes as far as proposing to Dorothy. However, Michael is in a complicated relationship with Sandy as he slept with her after undressing to try on one of her dresses for Dorothy to wear. Then there is also Julie, whom Michael has a crush on but Dorothy is more like a mother figure to her.
Dorothy's character (Emily Kimberly, hospital administrator) is so popular that she is asked to sign another contract but Michael wants out. His big reveal is not to be missed. The fallout probably should have been worse, and a lawsuit probably would have occurred in real life.
Dorothy is surprisingly feminist. Too bad her theories on women don't transfer over to Michael who even follows Julie's pick-up advice to the letter and gets a drink dumped on him and he ignores Sandy, as though they had never had sex. However, many female fans think that Dorothy is a huge role model for them.
Dustin Hoffman is brilliant; this is certainly another one of his timeless roles, along with Rizzo in Midnight Cowboy, Raymond in Rain Man and Benjamin in The Graduate. The rest of the cast is also brilliant, including the director Sydney Pollock as Michael's agent, George Fields.  The film is hilarious. However, though Michael's big reveal is hilarious, I didn't like it much. Oh well, a small problem. To Michael, Dorothy taught him what a woman really goes through in a day and how men take advantage of them (literally and figuratively). Hopefully, he'll become a better man for it. Being a woman is complicated. Grade: A