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It's been nearly 31 years since Sydney Pollack's Tootsie made its debut, but still the comedy that earned ten Academy Award nominations—and a win for supporting actress Jessica Lange—is considered one of the best ever made. The setup seems silly, but its message about gender inequality still packs a punch. An actor (played by Dustin Hoffman) is fed up when he can't get cast, so he changes his niche by masquerading as a woman named Dorothy Michaels. As a fiery actress, he lands a coveted role on a popular soap opera, and finds it’s the role that changes his life in ways he'd never imagined. The former ladies man becomes an unexpected feminist when waking in another (wo)man's shoes shows him how skewed the world is against the so-called "fairer" sex.
With a whip-smart script from Larry Gelbart and Murray Schisgal and outstanding performances from Hoffman and Lange, as well as Charles Durning, Teri Garr, and Bill Murray, it's little surprise that Tootsie still ranks on both the American Film Institute's Top 100 Movies and on their Top 100 Laughs. It's #69 on the former, and #2 on the latter, second only to Billy Wilder's cross-dressing comedy Some Like It Hot. Fitting then that it's a video from the AFI archive that has brought Tootsie back into the spotlight. In the clip above, tipped by The Mary Sue, Hoffman talks about the makeup tests for the film, and how pivotal they were to his understanding—not just of his character—but of the gender politics we are all subject to in this world.
"If you were born a woman, how would you be different?" Tootsie co-writer Murray Schisgal aked Hoffman as he prepared for the role of Michael Dorsey/Dorothy Michaels. Not "What does it feel like to be a woman?" It's a subtle distinction, but the emphasis on his own identity intrigued Hoffman. The actor, who had long before won acclaim and professional respect for roles in Midnight Cowboy and The Graduate, considered this hypothetical question for years before the film had even found its director. As part of his preparation, Hoffman asked Columbia to pay for make-up tests so he might actually see what he would look like if he had been born a woman. The results shook him to his core completely.
Hoffman initially wanted to be sure he could look like a believable woman who would walk by unnoticed on the streets of New York, and not some obvious "guy in drag" or a "freak." He didn't want to strain the audience's suspension of disbelief. But when it actually came down to seeing himself in this woman look, he was shocked he wasn't an attractive woman. So, he asked them to do it again, but this time, make him beautiful. "I thought I should be beautiful," he explains. However, they broke it to him: this is as pretty as we can make you. Hoffman tears up at the memory of what happened next:
"It was at that moment I had an epiphany, and I went home and started crying. Talking to my wife, I said I have to make this picture, and she said, 'Why?' And I said, 'Because I think I am an interesting woman when I look at myself on screen. And I know that if I met myself at a party, I would never talk to that character because she doesn't fulfill physically the demands that we're brought up to think women have to have in order to ask them out. She says, 'What are you saying?' And I said, 'There's too many interesting women I have…not had the experience to know in this life because I have been brainwashed. That (Tootsie) was never a comedy for me."
This quote speaks for itself. But if you want to hear more, you can find a fuller version of this interview on the Tootsie DVD. And you can also see the film's trailer below if you need a more general reminder of the movie's brilliance.