Spoiler Alert: It's more complicated in heels!

Movie: Tootsie

Rank: 69

Year: 1982

Director: Sydney Pollack

Cast: Dustin Hoffman, Jessica Lange, Teri Garr, Dabney Coleman, Bill Murray

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While disguising yourself as a woman to get ahead in your career feels like a distinctly male notion, what ensues is a soapy, fun ride of a prickly actor finding his foothold in the industry while gaining some knowledge of the plight of women in the workplace.

Acting teacher Michael Dorsey has become infamous for being difficult to work with on set and stage. When his agent informs him no one will hire him, he decides to turn himself into a woman to land a soap role in order to be able to fund his roommate’s play. Matters are further complicated after sleeping with a friend, falling in love with a costar and being hit on by a few men in his life.

Unexpected to him, Dorothy and her off-script antics become an icon for women in America and a smash hit. When faced with the prospect of a year-long contract and confusing emotions with his costar, Michael takes the opportunity of a live reshoot to out himself not only to those he works with, but also the audience. While no firm resolutions are set out, things seem to definitely be headed in a positive direction for Michael.

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"I don't believe in hell. I believe in unemployment, but not hell."

- Michael Dorsey

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With a score made for a 1980’s sitcom, I kept expecting Alan Thicke to pop out of a doorway to deliver some of his hallmark Dr. Seaver fatherly wisdom.

A movie clearly marked by its time period, it exists in the heyday of soap operas or “daytime dramas.” The fast-paced shooting schedule allowed Dorothy to ad-lib and get away with it; and the infiltration of these daily stories in American homes allowed her to gain national recognition. In an age where soaps are ending after decades on air and seasons are being renewed on a year-to-year basis, Dorothy’s meteoric rise and self-shaping image wouldn’t happen today.

Really embracing the tropes of an industry film, what would this movie be without its audition and shopping montages? Not only do we get a sense for how high maintenance Michael can be, but also for how great his transformative skills are.

We can talk about how Michael with all of his male privilege and confidence had the gall to speak out against on-set sexist behavior when he experienced it directed toward him for the first time. We could also talk about how his brazen attitude in a scene was only tolerated because of his immense popularity. However, what I really want to talk about is how there must be a Mommy complex in Hollywood because every guy to woman transformation in a movie involves an age-up. Mrs. Doubtfire made sense with his effort to be unassuming to gain visitation with his kids, but Dorothy really backed herself into a corner while also faced with old men who couldn’t take a hint.

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"This is our first date, I just want to look pretty for her."

- Michael Dorsey

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While parading around as this grandmother-esque figure, Michael was acting like a grade-A dick to poor, confused Sandy, a friend of his for six years. After being caught literally with his pants down, in an attempt to quickly try on her dress while she showered, he made a move and they slept together. Despite her asking him to just call it off from the beginning, he lies to her and causes her to literally chase him down.

While I have a hard time seeing this as AFI-worthy, it was if nothing else, a fun adventure in one actor’s poor decision-making which yielded positive results. I must believe its place on this list is in part due to Dustin Hoffman’s mainstay in American cinema. Its casting has also aged well, with Bill Murray as the sarcastic in-the-know roommate, Geena Davis’ in her feature film debut and Jessica Lange as a fearsome single mother and leading lady.

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"You know, I could lay a big line on you and we could do a lot of role-playing, but the simple truth is, is that I find you very interesting and I'd really like to make love to you."

- Michael Dorsey

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Post-script: Shout out to these on-screen parents from pinnacles of my 1990’s childhood. I must assume Teri Garr tried her hand at acting some time between giving up and reuniting with her daughter, Phoebe Buffay. I wonder if she knows she’s only a few degrees away from the President’s Daughter?