Seeking out the

5000 greatest films

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Tootsie
Hollywood's most exquisitely constructed comedy

Tootsie was a foundational film for the young, impressionable me. I saw it at age eleven in 1982, when it was first released. The teaser trailer, featuring a slow pullback of Dustin Hoffman stretched out in a bathtub shaving his legs while a voice-over sets up the premise, is the first memory I have of seeing any trailer. It served its intended purpose of spiking my curiosity, and when I did see the movie, Tootsie did not disappoint. I laughed and laughed and laughed, even though much of it went right over my head. When the nineteen-year-old me was studying film in NYC and bought my first laserdisc player, the Criterion Collection edition of Tootsie was one of the thirty discs I had in my collection that I watched innumerable times. I studied it intensely, trying to understand what made it so endlessly rewatchable to me. There are a lot of nostalgic reasons why Tootsie ranks so high on my list of favorite films, but after decades of film watching, I believe it deserves its spot because I'm a structure fanatic, and I consider Tootsie the most exquisitely constructed comedy ever made.

Like Casablanca, Tootsie was the product of many creative folks, including a significant number of talented screenwriters. The project began life as an unproduced stage play called Would I Lie to You? by Don McGuire, about an unemployed male actor who cross-dresses in order to get jobs. Buddy Hackett was originally attached to star in a film version, but the production never came together. The script kicked around Hollywood for years, going through the hands of many development execs, actors, and screenwriters. The premise was maintained, but the lead character was often changed from an actor to a tennis player, a chef, or various other professions. Nothing stuck until Dustin Hoffman read a draft of the screenplay written by director Dick Richards, producer Charles Evans, and screenwriter Bob Kaufman, based on McGuire's original. By this point, the script focused on an out-of-work male actor who got a job playing a female nurse on a popular TV soap opera. Hoffman bought the film rights and started to develop it for himself to star in, hiring writer Murray Schisgal to make the film less of a broad farce and more a grounded but comical exploration of the premise. Hot off his experience in Kramer vs. Kramer (1979), Hoffman was drawn to the material, seeing compelling similarities and resonances between the two works. As with Kramer he perceived the protagonist to be a traditional-minded male character who must learn to access the feminine aspects of his personality in order to become a more complete, well-rounded individual. Hoffman also saw this new role (as the character does) as "one of the great acting challenges of all time."

At this point, Dick Richards and Charles Evans were on the project as director and producer. Hoffman clashed with both men, and they departed over creative differences. Hal Ashby signed on to direct, but he had conflicts with the studio, Columbia Pictures, who fired him and brought on Sydney Pollack. Pollack wasn't crazy about the script as it stood, so Larry Gelbart (the veteran TV writer of Caesar's Hour and M*A*S*H, and book writer of the Broadway hit A Funny Thing Happened on the Way to the Forum) was hired to do another rewrite. It was clear that Hoffman was never going to be credible playing a sexy nurse on a TV soap, so the fictional actor was now pursuing the role of a tough hospital administrator. Pollack also clashed with Hoffman, as pretty much everyone who worked with the volatile actor did at this point in his career. But Pollack saw in Hoffman the exact kind of strength, insecurity, talent, ego, passion, and infuriating difficulty working with others that he wanted in the main character, now named Michael Dorsey. He encouraged Gelbart to put more and more of Hoffman's personality into the character of Michael.

The contentious behind-the-scenes relationship between director and star worked its way onto the screen as well. Pollack had cast his old friend Dabney Coleman to play Michael's agent, George Fields. But Hoffman didn’t find Coleman intimidating enough. Like Pollack, Hoffman was a stickler for credible character motivation, even in a broad comedy, and he didn't believe his character would put on a dress to get work if Dabney Coleman told him no one wanted to work with him. Hoffman thought he'd just tell Coleman to fuck off. But Hoffman was intimidated by Pollack and said that if he told him no one in the industry wanted to work with him, he might consider disguising himself as a woman and start auditioning for female roles. Pollack, who had started out as an actor, reluctantly agreed to play the part. It turned out to be an ideal piece of casting. In fact, the experience made Pollack view himself as an actor, and other directors later followed suit. We probably have Tootsie to thank for the great director's memorable turns in Husbands and Wives (1992), The Player (1992), Eyes Wide Shut (1999), Michael Clayton (2007), and others.


Coleman was reassigned to play the arrogant, chauvinistic soap opera director Ron Carlisle. The Ron character is romantically linked to the show's leading lady, Julie Nichols, whom Michael Dorsey (pretending to be actress Dorothy Michaels) befriends and falls in love with. The switch turned out to be inspired casting because, by this point, Coleman had played the ultimate male chauvinist boss in 9 to 5 and had developed a prickly screen persona that perfectly suited the part. Ron possesses many of the same negative attributes as Michael. Thus Michael (disguised as Dorothy) is forced to see and judge his own behavior—specifically the ways he has treated women—via looking at the funhouse mirror of Ron. Gelbart even has Ron say some of the same lines we hear Michael say earlier in the film back to him, justifying his infidelities and attitudes. When we hear these sentiments coming from Dabney Coleman, we're far less forgiving of them than we were with our protagonist—and so is Michael.

The role of Julie Nichols was difficult to cast. In most versions of the script, she was little more than a beautiful and vulnerable soap star. Even in the excellent draft Gelbart turned in, which Pollack and Hoffman liked enough to start casting and Columbia liked enough to green light, Pollack believed the script needed more work. He became aware of Jessica Lange when his daughter convinced him to watch the Dino De Laurentiis remake of King Kong (1976). He disliked the film but was mesmerized by Lange in the Fay Wray role. Even though he lacked a completed script he was satisfied with, Pollack offered Lange the part of Julie. He explained to her that he often started a picture without the script being ready, and he promised the part would be worthy of her once cameras rolled. She trusted him and signed on. Lange makes Julie a deeply sympathetic character. She could easily come off as a pushover. But the final film provides Lange with many scenes outside of the TV studio, where we come to understand not only Julie's specific circumstances but also gain insight into the life of an actress on a daytime TV drama at the beginning of soap operas' peak popularity. Julie is the least comedic role in the entire film, and Lange is required to make her feel credible in many wildly exaggerated situations.

The role of Sandy, Michael's neurotically insecure actor friend, was another that Pollack felt was underdeveloped. He brought in Elaine May, then as well known in Hollywood for her abilities as a script doctor as she was for her comedy or her acting and directing career. May poured much of herself and her observations about New York actresses into Sandy, and Terri Garr was cast to bring them to life. Garr's comedic chops are on full display in Tootsie. She was, at the time, a bigger star than Lange, having appeared in the hits Young Frankenstein (1974) and Close Encounters of the Third Kind (1977). She had just come off of her starring role in Francis Coppola's musical One from the Heart (1981), which was turning out to be one of the biggest bombs in cinema right around the time Tootsie wrapped shooting. Its lack of success might have helped her tap into Sandy's insecurities. Both Garr and Lange were nominated for Best Supporting Actress Oscars for Tootsie. Of course, in typical Oscar campaigning shenanigans, Lange really belongs in the Lead Actress category. The studio justified her placement with the absurd notion that Dustin Hoffman was both the Leading Actor and the Leading Actress in Tootsie, which is ridiculous since Michael Dorsey and Dorothy Michaels are the same character. It was more the case that Lange was already up for consideration as Lead Actress for her starring role in Frances (1982) that same year. Lange won the only one of Tootsie's ten Oscar nominations—a rare case of an actor getting nominated in two different categories in the same year, that actor not splitting the votes cast for them between the two categories, and two actors from the same movie nominated in the same category not canceling each other out.


Elaine May's contributions were not limited to enhancing the lead female roles. Knowing Hoffman had shared apartments with many fellow thespians (including Gene Hackman) when he was a struggling New York actor, she added a roommate character for Michael. She made the roommate a playwright rather than another actor so there would be nothing competitive between them and so the dynamics of the Sandy character could be more fully explored. May set it up so that all three characters have the common goal of producing a play together if Michael can successfully raise the money via his soap opera stint. It was also May's suggestion that Bill Murray play this roommate character. By this point, Murray had broken out from Saturday Night Live and become a major star in Meatballs (1979), Caddyshack (1980), and Stripes (1981). But he was far from the kind of New York theater-trained actor that Hoffman and Pollack were used to. May assured them they would not regret casting Murray if they could find him at such late notice. He famously had no agent (as is still the case), and the only way to offer him parts was to leave a voice message on his listed phone number. Murray was excited to get the chance at a more traditional role in a more prestigious movie than he was used to. He agreed to sign on but stipulated in his contract that he would be uncredited and that Columbia would not publicize his participation in the film so that his appearance would come as a surprise.

The addition of Murray was inspired, and Pollack found him a fascinating actor to work with. A birthday party scene in the first act of the script called for all kinds of expository info dumping, which Pollack had hoped May would improve. She told him she didn't write party scenes because all party scenes in movies come off as totally fake. In the end, Pollack never got the party scene in the shape he wanted on paper, but when the time came to shoot, knowing Murray's skills as an improviser, he asked him if he could just sit at a table surrounded by attentive listeners and just talk about being a writer in a way that sounded deep but in the end was kind of meaningless. Murray said, "Sure, I can do that." Pollack just rolled film on Murray, gradually having the extras leave until only one person was left listening to him going on as if he had the same audience he’d started out with. By interspersing this little improv shot into the scripted scenes of Michael using the same pick-up line on a number of women and striking out, the party scene took up little screen time but conveyed the necessary feeling of time passing. In a later scene, Murray asked Pollack if his character could be eating raw lemons as he gives Michael some advice at a crucial juncture. The idea made little sense to the director, but he was impressed at how this odd acting choice heightened Murray's performance at this key moment. When you watch the film, you don't really notice what Murray's character is eating because you're so focused on the intensity of the warning he's giving Michael.

The rest of the Tootsie cast fell into place perfectly. Pollack and the legendary casting director Lynn Stalmaster made sure the right person was placed in even the smallest roles. For example, the great Chicago stage actor Lynne Thigpen plays a tiny part as the floor manager on the soap opera. She has practically no dialog but makes a memorable impression nevertheless. Gelbart, one of the best gag writers of all time, gave some of the most memorable zingers to characters who only speak that single line. During Dorothy's audition, the soap opera’s producer, Rita, states that she’d like to make Dorothy look a little more attractive and asks the camera operator how far he can pull the camera back. He responds with, "How do you feel about Cleveland?" The line always gets one of the biggest roars of laughter from every audience I've ever watched this with.

Another example of a tiny role that makes a big impression is Geena Davis's turn as soap star April Page, with whom Dorothy shares a dressing room. Making her acting debut in the picture, the six-foot-tall fashion model towers over the diminutive Hoffman in their scenes together. The role only required Davis to look jaw-droppingly gorgeous in her underwear to unsettle Michael Dorsey as he attempts not to ogle her while disguised as Dorothy. But Davis also has many great comic moments in the film. Pollack and editors Fredric and William Steinkamp frequently cut to her hilarious reaction shots to enhance key sequences, and she has several subtly funny lines that probably would have hit the cutting room floor had they not been delivered by such a gifted actress. Davis possessed the perfect blend of sexy, goofy, and physically imposing to make this bit part stand out, and it's not surprising she went on to become one of the biggest stars of the '80s and '90s. In the more substantial role of Julie's widower father, Les, the multitalented Charles Durning utilizes many of his theatrical gifts, including his skill as a dancer. Les's attraction to Dorothy makes the fact that Michael is falling for Julie all the more complicated. The great New York stage actor Doris Belack plays Rita, the soap opera's producer, a formidable woman who responds positively to Dorothy Michaels because she recognizes aspects of herself in the strong, self-possessed "actress."

George Gaynes, then a working stage actor with few significant credits to his name, auditioned for the role of the lecherous, aging soap star John Van Horn and was shocked when he got the part. Gelbart and Schisgal had pulled off a great bit of writing with this character. John Van Horn is a comically inept individual that no one takes seriously as he persistently tries to seduce all the women on the show, including Dorothy. His inability to take no for an answer is always played for laughs until he ends up in Dorothy/Michael's apartment in a confrontation that almost turns to rape. Gelbart had devised the way that Michael, as Dorothy, is forced to let him up to the apartment by having Van Horn serenade Dorothy from the street, waking the neighbors and causing a scene. It was a farcical idea that the stringent realist Pollack never thought would be credible until he saw a videotape that casting director Stalmaster made of Gaynes singing as the character. The tape convinced the director that the scene would play as both laugh-out-loud hilarious and plausible—which it does.

One more small but key contribution to the script came from the screenwriting team of Barry Levinson and Valerie Curtin. In order to draw the parallels between Michael Dorsey and the insensitive chauvinist soap opera director Ron Carlisle, Pollack wanted Michael and Sandy to be sexually involved. Neither he nor the other collaborators could come up with a simple way to get these two platonic friends into bed. But Levinson and Curtin, who were married at the time, came up with a simple answer to this problem while they were getting ready for a party one night. They envisioned Michael trying on some of Sandy's dresses, her catching him undressed by her closet, and him concealing the true reason for being naked in her bedroom by coming on to her. If you count this not-inconsequential contribution, the number of writers on this script had risen to about seven or eight, and Pollack was the kind of director who liked to run all his scripts through his own typewriter before finalizing them. Prior to his taking this last step, he and Hoffman had countless script sessions. Pollack had gone back and re-read every single draft that had been done to make sure there wasn’t any little nugget that had fallen through the cracks. Turns out there was. Way, way back, possibly in Don McGuire's original play, a scene existed in which the actor pretending to be a woman has a late-night heart-to-heart with a beautiful actress he's co-starring with. She tells him what she would really like to hear a man say to her instead of the same-old insincere pick-up lines. Later on, while not disguised as a woman, the actor meets up with the actress at a party, pretends not to know her, says what she said she wanted to hear from a man, and she slaps him in the face. Pollack thought that idea was way too good to leave out, and he incorporated it into Michael and Julie's relationship.

As they neared production, one of the director's biggest concerns was that the script's first act was way too long. In their initial script development, Hoffman and Schisgal had done extensive research into how a man who looked like Hoffman could pull off passing as a woman. They met with drag queens and female impersonators to learn things like where to buy shoes, how to hide five o'clock shadow, what makes the most realistic looking falsies, and so on. One detail they loved came from a drag queen who told them that birdseed made the best fake breasts because of the way it moved around inside the cups of a bra. Hoffman wanted all the research that he had done to be part of the work we see Michael doing in the film, but Pollack wasn’t convinced. While that material was interesting, this movie wasn’t about how an actor learns to play a woman. He suggested Gelbart remove anything from the script that didn’t serve the theme that had attracted them all to the project in the first place—the story of a flawed guy who becomes a better man as a result of having been a woman.

In the end, not a single scene of Michael Dorsey preparing to become Dorothy Michaels remained in the first act. Pollack's gamble, and he did feel it was a real risk, was to not show any of what the shlubby Michael must have undertaken to pass himself off credibly not only as a woman but also as a professional actress. There isn’t even a preparation montage—and this is a movie filled with amazing ‘80s-style montages. Set to Dave Grusin's jammin' theme music and some memorably of-their-time songs performed by Steven Bishop, Tootsie is awash in montages. The ultra-'80s blue silhouetted "Take My Breath Away" sex montage in Top Gun has nothing on the gauzy, slow-mo salad tossing and candle lighting images underscored by Steven Bishop singing "Something's Telling Me It Might Be You" in Tootsie.

But nothing like that occurs in the turn from Act One to Act Two of this film. Pollack and Gelbart had whittled down all the exposition required for the story into an opening credit sequence that tells the audience everything we need to know about Michael Dorsey: he's a great actor but a difficult person to work with, and he's an acting teacher who preaches to his students that they must do anything to get work. Pollack was the kind of director who felt even farce must be credible and logical, or else it's all just contrived. But he believed that Hoffman could sell the idea that Michael was such a good actor that the audience wouldn’t need to know how he transformed himself convincingly into Dorothy. Hence, the incredible ellipse cut that takes the story from its first act into its second. We learn that Michael feels he has no choice but to disguise himself as someone else to pursue a well-paid role on a TV soap. There is then a hard cut to what is now colloquially known as "The Tootsie Shot." In this long-distance, telephoto widescreen shot, a sea of New York City pedestrians walk along a busy street, and our main character slowly emerges to become the focal point of the shot. The rest of the rush hour crowd then fades into a soft blur.

This shot has been used in countless New York movies before and since—including Hoffman's own Midnight Cowboy (1969), as well as Stayin' Alive (1983), Ghostbusters (1984), Crocodile Dundee (1986), Heartburn (1986), Wall Street (1987), Baby Boom (1987), Working Girl (1988), Bridget Jones's Diary (2001), Elf (2003), The Devil Wears Prada (2006), and The Wolf of Wall Street (2013). But I think it has come to be known as "The Tootsie Shot" because this movie represents the single best example of its use. In part, that's because the cut to the shot serves as the act break, and in part, it's because it takes much longer to realize who we're supposed to focus on than is typical. With John Voigt in Midnight Cowboy or Paul Hogan in Crocodile Dundee, the point of the shot is to emphasize that they are fish-out-of-water characters, but the more typical use is to pull one anonymous member of a crowd out and visually state to the audience that this person is important, with a story about to be told.

The man behind the quintessential example of this shot was Owen Roizman, who by now had worked on three prior films with Pollack. The director and cinematographer had an easy working relationship that translated into a great-looking picture. With the exception of some of his earliest movies, like They Shoot Horses, Don't They? (1969), Pollack was always a director who liked his movies to look classy and a bit more attractive than real life ever gets. At this point, New York City was undergoing a makeover. Shedding its 1970s reputation as a crime-ridden cesspool of muggings, stabbings, and ineffective government, the city was luring tourists back with its "I Love New York" promotional commercials. By 1980, Governor Hugh Carey declared that the jingle created for these TV spots was to become New York's official state anthem. And ever since Woody Allen's Manhattan in 1979, filmmakers had realized that the city could be beautiful and romantic as much as it could be gritty and threatening. The look Roizman created for Tootsie suits it so well because Michael Dorsey is the opposite of a fish out of water. He's a small, nimble New York actor used to darting around the streets, shops, restaurants, studios, subways, eight-floor walk-ups, and sprawling, unfurnished loft apartments.