Man. Some Like It Hot and now Tootsie. Apparently, I really like movies about cross-dressing. What can I say? These comedies are hilarious! And what I love about Tootsie in particular is that it fits right in with the screwball comedies of the 30s and 40s. It’s a satirical love story with quick and witty dialogue, and with an outlandish premise. Dustin Hoffman’s ability to transition from Michael Dorsey to Dorothy Michaels and back within the same scene is a level of acting that has rarely been duplicated. From the walk, to the posture, to the talk – he nails it. It’s certainly more convincing than Tony Curtis and Jack Lemmon. It’s impossible to imagine anyone other than Dustin Hoffman in the role, so it’s probably a good thing production was delayed long enough that neither Michael Caine or Peter Sellers could take it.

Michael Dorsey is a struggling actor in New York City. Between specific qualities wanted for roles and Michael being difficult to work with, it’s been months since he’s successfully landed an acting job. His friend, Sandy, casually brings up a role she’s pursuing – the hospital administrator for the soap opera, Southwest General. Desperate for work not in a restaurant or classroom setting, Michael disguises himself as a woman, Dorothy Michaels, and lands the part. Dorothy takes charge of her part, playing the administrator, Emily, as a strong, confident feminist, which makes her a national sensation. To look for clothes for Dorothy, Michael raids Sandy’s closet, but she catches him in a state of undress and plays it off that he wants to sleep with. She reciprocates. However, Michael is actually falling in love with one of his costars, Julie, who is also the girlfriend of the soap’s director, the sleazy Ron (if you recognize the guy in this role, it’s because he plays the equally sleazy boss in 9 to 5). Julie and Dorothy become close friends, and it’s Dorothy who encourages Julie to end things with Ron for her own well-being. Dorothy has a couple of admirers of her own, the veteran actor on the soap, John, and Julie’s father, Les. Les goes so far as to propose marriage to Dorothy. John just shows up to her apartment and attempts to put himself on her. As soon as John is removed from the apartment, Sandy shows up, having been ghosted by Michael since their night together. Michael admits to her that he’s in love with someone else, which obviously upsets Sandy. To get out of his contract, Michael sets up a situation where the soap has to go live for their next episode and reveals himself a man, claiming to be Emily’s brother, Edward, who is seeking revenge for Emily’s “murder”. The reveal is a shock to everyone and Julie punches Michael as soon as the cameras stop rolling. Some time later, he approaches Julie to apologize and admit that “I was a better man with you as a woman than I ever was with a woman as a man.” Julie admits to missing Dorothy’s company and they walk down the street in conversation.

I’ve already said plenty on Dustin Hoffman’s performance, but alongside that, it should be mentioned that Hoffman has been on record multiple times to explain what the role in Tootsie has done for him. He claims that playing Dorothy allowed him to realize that he found the woman incredibly interesting, but because she’s unattractive, if she were a real person, he never would have approached her. He felt ashamed of his internalized sexism. While that easily sounds like a celebrity posturing to make themselves sound better, it still opens up a conversation about the truth behind what he’s saying. That’s what all the best comedies do anyway – open the doors that would otherwise remain closed. I guess it’s true what they say: you can’t judge a woman until you’ve walked a mile in her heels.

Bonus Review: Mrs. Doubtfire

Speaking of men dressing as women for the sake of work, there was another film, very similar to Tootsie, that came out eleven years later: Mrs. Doubtfire. I expect most of my readers have seen this film, so it’s not much of a recommendation to watch something new as much as a recommendation to rewatch this hilarious movie from one of the greatest comedy talents ever to walk the earth.

Daniel quits his job as a voice actor over a scene that he argues encourages kids to take up smoking. He picks his three children up from school, and takes them home to have a birthday party for his son, Chris, despite, Miranda’s, his wife, objections. Miranda, who is very devoted to her job, returns home and sees the chaos ensuing in her living room. In her frustration and with the news that Daniel quit his job, Miranda decides to divorce. Because of Daniel’s lack of a job or home, Miranda gets sole custody of the children. Daniel gets a job in shipping at a television station, and then, when Miranda reveals she’s putting a want ad in the paper for a nanny, he takes a second job. His brother who is a makeup artist helps Daniel create Mrs. Doubtfire, the greatest nanny across two continents. As Mrs. Doubtfire, Daniel is very strict with his children, allowing them to be more disciplined and Miranda to be more relaxed, and Daniel himself becomes more responsible. After hours, Daniel is caught playing with some of the props for the children show the station works on by the CEO, Jonathan. Impressed by his talent and imagination, Jonathan invited Daniel to dinner to discuss ideas. The same night, Miranda is having a birthday dinner at the same restaurant with her new boyfriend and the children and insists Mrs. Doubtfire join them. Daniel must juggle both dinners to little success. However, Miranda admits his help in raising their kids is best for everybody so she works out a joint custody deal. He also becomes the star of a successful children’s show, as Mrs. Doubtfire.

I know I’ve reviewed Good Morning, Vietnam already, but I’ll mention it again because that film left so much open room for improvisation that some of Robin Williams’ monologues feel like retreads of his stand-up specials. There’s no harm in that fact. The material’s funny so why would anything else matter? However, Mrs. Doubtfire is significantly more structured than Good Morning, Vietnam, which means that Williams’ improv had to fit the scenes and was much more tightly leashed. This also means that the comedy in Mrs. Doubtfire feels more original. So when Williams, as the Doubtfire character, is ignored in his attempt to discourage his ex-wife from wearing sexy clothing on a date and instead suggests an ugly frock, his comment that he will “get the frock out of here” is immaculate. Or when he throws a fruit at Pierce Brosnan’s head, he can claim as a witness that it was “a run-by fruiting”. It’s a film that is hilarious, joyful, and tender.