2 Movies 1 Moment: When a Man Wearing a Dress is More Than Just For Laughs

Men dressing as women in theater is certainly nothing new as actors were exclusively male for centuries. In modern times, the sight of a man in women’s clothes is mostly used for a gag, and has allowed many of Hollywood’s more manly men to get a laugh in drag. But more significant roles have found some of cinema’s finest actors don a dress and do more than make a comedy. Here are two men in dresses that gave us a smile plus a lot of heart.

Melissa’s Pick: Mrs. Doubtfire (1993)

Film Summary: Daniel (Robin Williams) and Miranda Hillard (Sally Field) are going through a messy divorce. Miranda has been granted custody and Daniel has been racking his brain trying to find a way to see his children more often than once a week; it’s not an option for him to not see them. He also needs to get a new job if he ever wants to get joint custody. His employment history hasn’t been the most stable and the social worker seems to have something against him. Just when everything seems to be at its most bleak, Miranda comes over to pick the kids up after having dinner with Daniel and explains that she has to go to the newspaper to drop off a listing for a nanny. Immediately, Daniel gets the idea that he should be the one to pick them up before and after school, that way he can see them every day. Miranda shoots the idea down right away. That’s when Daniel changes the phone number on the listing so no one else will call and starts making calls to Miranda using different personas until he comes up with the winner: Mrs. Doubtfire.

The Moment: Now that Daniel has created Mrs. Doubtfire and Miranda wants to meet her, he goes to his brother, who is a makeup artist, to make Mrs. Doubtfire a reality.  More than happy to help, Daniel’s brother and his boyfriend start the process of transforming Daniel into Mrs. Doubtire. They try a latina makeup, a very elderly woman, a sassy redhead and then, with the sound of Luck Be a Lady by Frank Sinatra playing in the background, Mrs. Doubtfire comes to life. First we see the makeup and then we see the shappings of the outfit; panty hose being pulled up over tremendously hairy legs, the back of the skirt being zipped up and buttoned, adjusting the pin at the neck of the blouse, and finally a shot of the shoes as the camera pans up and we are able to see the back of the ensemble. Daniel nervously asks, “How do I look?” to which his brother responds, “Any closer and you’d be mom.” Our moment finally arrives a few seconds later when the doorbell rings at the Hillard residence, Miranda opens the door and we are able to see the whole thing top to bottom, Daniel completely reinvented as Mrs. Doubtfire wearing a thick wool skirt, white blouse and lovely cardigan.

Why it Matters: This movie has so much heart and this moment shows us just how great of a person Daniel is. He is willing to do anything to be with his children; he’s willing to break social norms, overcome any obstacles and even become a completely different person just to be close to them. This moment brings all of this to striking clarity. For some reason, it doesn’t seem like that much of a stretch for a woman to dress like a man, but when a man dresses like a woman, it’s a real testament to their determination and it seems like the furthest length to which a person can go to accomplish a task. There is no doubt that Daniel loves his children and that he would do anything for them. Hearing Daniel call Miranda as different characters is hilarious, as is seeing the different characters that Daniel’s brother creates for him but seeing him standing in the doorway of his own home dressed as a woman and pretending to be a stranger is so astounding.  The transformation here is really incredible. Also, Robin Williams is wonderful. RIP.

David’s Pick: Tootsie (1982)

Film Summary: When a down on his luck actor – mostly because of his difficult to work with attitude – can’t find a job, he resorts to wearing a dress and presenting himself as a woman when he sees a role on a daytime soap opera that he thinks he can do. With some prosthetics, make-up, and the right wardrobe, he pulls it off and becomes a celebrity, fooling the nation into thinking Dorothy Michaels is a real person.

The Moment: None of it is going to matter if Michael (Dustin Hoffman) can’t fool his agent, so after he gets himself made up in his new persona, which baffles and yet intrigues his roommate (Bill Murray), he hits the streets and ambushes George (Sydney Pollack) at the Russian Tea Room, a famous restaurant in the city. First, out front, he tests the waters, “bumping” into his agent and asking him if he knows where the restaurant is, which of course they are standing right in front of. It’s just a ploy to see if Michael is immediately recognizable, and when it works perfectly, Michael, err Dorothy, follows him in and takes a seat right in the same booth, causing George to panic before Michael whispers his identity, inspiring the classing line: I begged you to get some therapy. Michael stays in character and continues with the lunch, fooling everyone around them and convincing himself that he can make it as a woman actor.

Why it Matters: Typically, a guy in a dress in a Hollywood movie is played for laughs, and certainly, Tootsie is no exception, but it does something else as well. While initially, seeing Hoffman in women’s clothes is a bit silly and maybe even awkward, something very interesting happens as the film progresses – we care about Dorothy! Hoffman make this character come alive, so much so we sometimes forget that there is a man under all that makeup and wigs. He is so convincing as a person, we gloss over the fact that it’s just a character. It is even a little sad when he strips away Dorothy and becomes Michael once again, proving just how impactful Dorothy was as a person and a role model. That we as the audience not only care about “her” but also sympathize with her, is a testament to how well the film was made and how well Hoffman dedicates himself to the role. Yes, we laugh when it starts, but feel changed when it’s over.