Why ‘Tootsie’ is One of the Finest (and Most Important) Comedies Ever Made

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In the first-season 30 Rock episode “Fireworks,” Liz Lemon and would-be beau Floyd fall asleep watching Tootsie. In their morning discomfort, Floyd awkwardly announces, “I, uh, I think Tootsie’s a very well-crafted movie.” Liz, equally uncomfortable, replies, “Yeah, they use it as an example in all the screenplay books.” As with the best of that show, it’s a moment that’s funny because it’s true — in this case, it’s literally true, Tootsie is a very well-crafted movie. But praising it solely for craft also shortchanges it a bit. The further we get from Tootsie — which is available for fresh consumption via Criterion’s recent DVD and Blu-ray special edition — the more it seems clear that it may, in fact, be the single finest comedy of all time.

To be clear, this doesn’t make it the funniest movie ever made (I’ll hold to my previous designation) — though it is very, very funny. Much of its crackerjack humor comes courtesy of the great Larry Gelbart (he wrote the book for A Funny Thing Happened on the Way to the Forum, developed M*A*S*H for television, penned Oh God!, and cut his teeth in Sid Caesar’s legendary writer’s room) who is Tootsie’s top-billed screenwriter. He shares that credit with Murray Schisgal, who’d developed the script with star Dustin Hoffman for years, based on Hoffman’s desire to make a film about what kind of a woman he’d be, if the circumstance presented itself.

Gelbart was a legendary jokesmith, and he wrote a first-rate farce and laugh delivery system; you can feel his influence in the traditional set-up/punchline bits (“Nobody wants to pay twenty dollars to watch people living next to chemical waste! They can see that in New Jersey!”), the expected complications (like our hero sharing a dressing room with a perpetually underclad Geena Davis), and the third-act physical and verbal chaos, which approach door-slamming farce. Gelbart wrote so many good lines, even the day players get some (“How do you feel about Cleveland?”).

The brilliant Elaine May was then brought in for an uncredited pass; Hoffman and director Sidney Pollack credit her for creating the roommate character, played so beautifully by an arid-dry Bill Murray, and fleshing out the female characters — particularly Terri Garr’s Sandy, whose neuroticism mirrors the kind of roles May would often play herself. (The script was notoriously worked and reworked; frequent Jerry Lewis writer Don McGuire, The Electric Horseman scribe Robert Garland, and future Rain Man director Barry Levinson all reportedly took a crack at it as well.)

To his credit, director Pollack took the best of what all those voices had to offer and weaved them into a remarkably unified whole. From its opening scenes, he’s quietly setting up little bowling pins to knock over later: the way Michael ignores the baby at his birthday party, how he callously tries to pick up women there, even a brief, early cutaway of a studio tech sipping beer next to a tape deck at the TV studio. Every beat is efficient — note how he cuts straight from Michael’s meeting with his agent to him in costume as Dorothy walking down the street, saving the transformation scene for later — and every moment is essential. Even the opening credit sequence functions as an orientation into the logistics of working as an actor, from vocal exercises to workshops to make-up to rehearsals to auditions to, of course, waiting tables. (If there’s any doubt to the film’s influence, watch the upcoming indie movie Loitering with Intent, which not only apes that opening, but literally quotes dialogue from Tootsie.)

That authenticity extends to the shades of autobiography in Hoffman’s performance; this was his Birdman, a role springing from his own reputation for prickliness (“Pardon me,” he announces to a dark auditorium in the middle of an audition, “but is my acting interrupting your talking?”). His bouts with Pollack in pre-production were so charged that he became convinced his off-screen director — who hadn’t acted in two decades — was the only one who could play his onscreen agent, and those scenes are charged with their real-life tension. “I’m trying to stay calm here,” Pollack tells Hoffman. “You are a wonderful actor. But you’re too much trouble.” Pollack had originally cast Dabney Coleman as the agent; Hoffman objected that the power dynamic wasn’t right, because Coleman was a peer. “Why make up what you don’t have to make up?” Hoffman reportedly asked Pollack — exactly the kind of thing Michael Dorsey might say. So Pollack took the role, shifting Coleman over to the role of the soap opera director (a smoother fit for the actor, who had become Hollywood’s go-to male chauvinist pig after 9 to 5).

Getting Pollack on as director was barely easier. When he saw Gelbart’s script, the filmmaker — not exactly known for his comic touch — turned it down. “I didn’t know what to make it about, other than the joke,” he recalled in 2007, and held to that until Hoffman and Schisgal explained the thematic spine that had drawn them to it. The final film tips that theme early on and off the cuff; in an offhand line, as they walk away from the camera, roommate Jeff tells him to stop trying to be Michael Dorsey the great actor or waiter, and “just try to be Michael Dorsey.” At the conclusion of the hilariously wandering, total-bullshit, improvised-on-live-television monologue wherein Dorothy finally unveils herself as Michael, he supplements the stuttering “deeply”s and “just”s with a clear confession: that he’d become “strong enough to be the woman that was the best part of my manhood. The best part of myself.” In his final scene with Jessica Lange’s Julie, he puts a finer point on it: “I was a better man with you, as a woman, than I ever was with a woman, as a man.”

Tootsie wasn’t the first feminist film from a major studio (or comedy, even; see the aforementioned 9 to 5), but it was one of the most important, because it was a giant commercial and critical hit. In many ways, it’s reminiscent of another broad comedy that supplements its screwball and slapstick with a subtle social message: 1996’s The Birdcage, also scripted (wouldn’t ya know it) by Elaine May. Both films made their progressive messaging palpable by giving it an approachable comic sheen, and by delivering it via a major movie star. The message can get a little scrambled, as you might expect from a feminist movie written and directed predominately by men — are they saying that it takes a man to start a feminist revolution? Maybe; I’m more inclined to think that, ultimately, at that moment in time, it’s simply a matter of someone not accustomed to that treatment speaking up. And his experience as Dorothy doesn’t just make Michael a better person. His influence makes shy, submissive, doe-eyed Julie stronger — not just with Ron, but with Dorothy herself, and ultimately with Michael.

In other words, it’s a movie with a lot on its mind — while never toppling over under the weight of its good intentions. In retrospect, it’s sort of genius, how they smuggled all that stuff in under the cover of a drag comedy, and promoted it not as a message movie, but as “Hey, look, Dustin Hoffman in a dress, funny!” He’s double-billed in the end credits, as Michael and Dorothy, and that’s appropriate — he creates two distinct characters, and acts both of them differently. “I think Dorothy’s smarter than I am,” he realizes, midway through his charade. And maybe that’s what Tootsie is really all about: when we dispense with our learned behavior and preassigned roles and macho bullshit, we can lean a lot from walking in someone else’s shoes.

Tootsie is out now from the Criterion Collection.