‘Tootsie’ at 40: Something’s telling me it might (still) be you – Retrospective

It may be the ultimate personification of the current zeitgeist, but discussion and consideration of gender roles, identification and fluidity is not new, nor is it revelatory, especially in the movies. Cross-dressing has been a part of entertainment since the beginning, from Shakespeare to the early days of film, to Monty Python to Some Like It Hot and Bosom Buddies. But it wasn’t until 1982 when a film took all the simply-for-comic-effect elements of dressing a man in women’s clothing and actually said something about gender in society, exploring some deeper truths about how we perpetuate gender roles—the exact truths that the younger generation today is spotlighting and attempting to change. Who knew that, forty years ago, one of the silliest, best comedy films of the twentieth century would turn out to have been so prescient and so ahead of its time—and stand the test of time the way it has. Well, anyone who has seen Tootsie understands. It not only is a funny, meaningful and memorable film, it is the greatest film ever made.

On this, the 40^th anniversary of the release of director Sydney Pollack’s masterpiece, Tootsie, I am honored to have the opportunity to put into words how much this film means to me, personally, as well as pay homage to its artistic greatness and place in American culture.

I was twelve in 1982 when Tootsie came out and I was living in Germany, so going to the movies wasn’t a big thing in my life. I honestly don’t remember when or how I actually saw it for the first time, but what I do remember is the lightning bolt that struck me when I did see it. At such a young age, most likely 13 or 14, Tootsie had such an impact on me, it set my life on a path that I still travel to this day.

No matter how much I had seen and loved other movies before seeing Tootsie, it was Tootsie that made me fall in love with cinema. There was something about it, from start to finish, all the elements that made me want to be a part of THAT. I set my mind on making a career in Hollywood, in some way, shape or form. When the time came to choose a college, my parents insisted on a liberal arts school, but I chose the one that was in Los Angeles, on the other side of the country from where we lived in the Washington, DC suburbs, instead of one of the many in New England, because it promised me a proximity to Hollywood and the chance at a college internship in the industry. I did go to that Los Angeles liberal arts college (Occidental College, whose alumni include Terry Gilliam, Ben Affleck and President Barack Obama), and I did get that college internship working for a small production company, which helped to crystallize what I really wanted to do, and that was write about film.

I started writing reviews for my college paper, then for the local community paper and for a couple nascent online publications (anyone remember Prodigy?). This was long before the internet as we know it, so options for film reviewing were few and far between. But what did arrive before social media was the idea of personal websites, what we now call blogs, and, in 2005, I registered my domain, CathsFilmForum.com, and I started to write, at first just for myself, then for friends, family and coworkers. I would go see a movie in the theater, come home and write my review and then send an email blast out to tell them it was there. I did this for fourteen years, until, in 2019, I saw an opportunity on Twitter to write for a real, professional film website, AwardsWatch, and the rest, as they say, is history. My very existence here, in this space, where you are reading these words, is all because of my deep, abiding love of film, my dedication to writing about it, and my commitment to continue the conversation about this incredible art form, and all its possibilities. And all of this, every single bit of it, including my career choice and where I decided to live my life, is all because of Tootsie.

Every time I tell someone that Tootsie is my favorite film of all time, I get a look that seems to be a befuddled understanding, as if to say “it was good, but the best EVER?” Admittedly, naming Tootsie as the best film of all time is an extremely subjective opinion, and I come to it largely due to my own sentimental attachment to its place in the trajectory of my life, but Tootsie is, beyond all subjective debate, an all-time classic of American cinema and it really shouldn’t come as a big surprise that anyone loves it as much as I do—and I refuse to believe I’m the only one.

The central storyline of Tootsie revolves around the character of Michael Dorsey, played by Dustin Hoffman, a struggling actor in New York City, who is desperately looking for work. When he takes his girlfriend, Sandy, played by Teri Garr, to an audition for a soap opera, Michael instantly connects to the part Sandy is auditioning for, which is written for a woman. So he puts on a dress, a wig and makes himself believable as a woman and gets the part. But Michael hadn’t put much thought into what would happen next, as his life is turned upside down when Dorothy, his alter ego, becomes a star on the show and Michael ends up falling in love with his co-star, Julie, played by Jessica Lange, who only knows Michael as Dorothy.

Tootsie took a long time to come to be, and involved many artists and took many shapes before it became the film that was released in theaters on December 17, 1982. What started in the ‘70s as a play by Don McGuire called Would I Lie to You? about an unemployed actor who dressed as a woman to get work, Tootsie only started to take shape as a film when Hoffman came aboard. Several directors were attached before Sydney Pollack, known for critically-acclaimed dramas like The Way We Were and Absence of Malice, was hired to direct and produce. But it was only when writers Larry Gelbart and Murray Schisgal signed on to write the screenplay that all the pieces fell into place. Gelbart, most famously known as the creator and writer for the legendary television series M*A*S*H, and playwright Schisgal wrote a brilliant script that expounded on McGuire’s original story by setting the film behind the scenes at a soap opera, and the comic genius just flowed from there. Although Gelbart and Schisgal got all the credit for the script (and the subsequent Oscar nomination for Best Original Screenplay), there were several uncredited writers who contributed, including Elaine May and Barry Levinson. May’s influence on the script is most likely what helps make this film still so palatable today, as what could easily have been a sexist romp is infused with feminist undertones.

Garr was concerned about those sexist elements before she signed on to play the role of Sandy, and it was the promise of being able to contribute some of her own lines, along with May’s dialogue, that convinced her to do the role. Garr’s performance is one of the most memorable performances in cinematic comedy history and yet it was her costar, Jessica Lange, who won the Oscar for Best Supporting Actress. Even now, forty years later, a heated debate still rages in film circles about who deserved to win between Garr and Lange. It is a testament to both actresses that, not only are their performances still so ingrained in our collective consciousness, but they both instill such passion from so many, most of whom weren’t even born when the film first came out.

Speaking of Lange, her Oscar was the only win for Tootsie at the 55th Academy Awards, a disappointing showing for the film, which had an astounding ten nominations. But it’s easy to forget what Tootsie was up against in 1982. Tootsie would have been the highest-grossing film of the year, if it hadn’t been for a little film called E.T. The Extraterrestrial, and it would have had the most Oscar nominations, with 10, if it hadn’t been for a little epic called Gandhi, which had 11–winning 8, including Best Picture. But, despite the strong competition from her own co-star within her category, Lange could not be denied.

When she was first offered the script for Tootsie, Lange had just finished filming a starring role as tortured actress Frances Farmer in Frances and couldn’t see herself following it up with such a light, fluffy part. But then, as Lange tells it, her Frances co-star, legendary actress Kim Stanley, insisted she take the role, if for no other reason than to shake off the trauma that making Frances had been. Lange did take the role in Tootsie, and ended up being a double nominee at the Oscars, her performance in Frances being universally lauded, but standing no chance in the Best Actress race, up against Meryl Streep’s career-defining role in Sophie’s Choice, so many consider Lange’s Supporting Actress win the Academy’s consolation prize. But what Lange did in Tootsie is vastly underrated, playing, ostensibly, the straight role, while everyone else got to be big, she had to be small and restrained. In the careful crafting of her character, Lange elevated Julie from being just a ditzy bimbo to someone real, warm, loving and honest. Lange’s performance adds a depth to Tootsie that is a dimension not seen on the page, and was completely deserving of its recognition. It is also fun to note, however, that, despite the fact that her first Oscar came for a comedy, Lange wouldn’t do another comedy for twenty-four years (Bonneville, in 2006).

As for Tootsie’s star, Hoffman, who was nominated for Best Actor, despite having won two Oscars for other roles, his performance in Tootsie is often considered the actor’s greatest achievement, and a big part of what made the film such a critical and commercial success. His well-documented perfectionist tendencies caused him to clash often with Pollack on set, which made for an uncomfortable environment at times, but resulted in a final product that was borne out of two artists duking it out, each one committed to their own vision. There was no lack of passion on the set of Tootsie, and it shows in the film itself, as every scene crackles with energy, whip smart dialogue delivered with perfect timing by some of the best actors in the business.

Hoffman’s dedication to making his character of Dorothy as believable and as real as possible is what saved Tootsie from being the butt of its own joke. If he had just put on a dress and a wig and expected us all to believe that he fooled everyone, both in life and in a soap opera audience of millions, the film would have bombed. Hoffman knew the success of the film hinged on him being able to pull it off, to make Dorothy believable as a woman. Before he even agreed to do the film, he made Columbia Pictures put up the money for full makeup and hair tests to see if it was even possible to fool anyone. What happened next, according to Hoffman, changed everything. When the makeup and hairstylists assured Hoffman that was the best they could do, Hoffman looked at himself in the mirror and realized, in that moment, that not only did they pull it off, but that he was not nearly as attractive as he thought he would be. In this moment of epiphany, he says he realized how brainwashed he had been his whole life into thinking that only beautiful women could be interesting and it was with the deeply felt mission of shining a light on that disgusting social construct that he went into making Tootsie. From that moment on, Tootsie was never a comedy for Dustin Hoffman, it was social commentary.

And it worked as both.

There are so few films that can stand the test of time the way Tootsie can. Michael’s transformation from shallow, arrogant and casually insensitive lout to a caring, compassionate and enlightened friend is one that is uplifting and hopeful, and is both skillfully and hilariously achieved. While the setting and characters may not be relatable to most, the existential struggle we all have with accepting who we are and finding the strength to change the things that are holding us back is universal. While it is a bit of a cliché that the only characters who are struggling to find their voice and stand up for themselves are women, both Julie and Sandy do eventually empower themselves to take charge of their own lives, and they do this on their own. The men are the butts of the jokes, not the women, and the more powerful and deluded the man, the harder they fall. We all love to see arrogant buffoons mocked, but, mostly, we love to see a character find humility and an understanding of their place in the world—and an understanding of how to make it better.

It would be so easy to say that it’s love that transforms Michael, but it’s more than that. It’s the realization, one that Hoffman himself had, that life as a woman, even if it’s just for one day, is much more difficult than for a man. It’s amazing how little has changed in forty years.

But let’s be real. Tootsie may have earned 10 Oscar nominations because of its ability to be much more than a one joke social commentary, but that’s not why it became the second highest-grossing film of the year and one of the top grossing comedies of all time. People loved Tootsie because it was unique, relatable and funny as hell.

There wasn’t a single weak element in Tootsie. Beyond the Oscar-nominated performances from Hoffman, Lange and Garr, scene stealing moments were turned in by every member of the cast, including the incomparable Dabney Coleman, who plays slimy soap director Ron with slithery appeal, Charles Durning as Julie’s hapless yet hopeful widower father Les, George Gaynes as John, the soap opera’s clueless letch, and Pollack himself, playing Michael’s exhausted agent. But it’s Bill Murray’s uncredited performance as Michael’s roommate, Jeff, that provided the key ingredient that was initially missing from the script. It was May who suggested they give Michael a roommate, in order to allow the audience to see a different view of Michael, in order to make him more vulnerable and appealing. Murray, who had just come off Stripes and Caddyshack, was one of the biggest comic actors in the world, but thought it would be hilarious to be uncredited in Tootsie. It turns out his presence helped to soothe some of the tension on set that existed between Hoffman and Pollack, and it was Murray who kept reminding them of how good the movie was that they were arguing about. Murray, who was allowed to pretty much write his own role and improvise most of his dialogue, delivers some of the best lines in the film as the easy-going and calm Jeff, the necessary antidote to every other decidedly stressed-out character.

Composer Dave Grusin imbues Tootsie with a light, jazzy sound, but it’s the Oscar-nominated love ballad, “It Might Be You,” that he wrote with legendary songsmiths Alan and Marilyn Bergman and performed by Stephen Bishop, that is the most memorable musical element of the film, which helped make it a Top 40 hit on the pop charts.

The editing, sound and cinematography were also nominated for Oscars, proving that Tootsie truly had all the elements working at the top of their game.

But, for me, it’s how Tootsie is the perfect example of a film that doesn’t waste a single moment of its just-under-two-hour runtime. Every scene is in service to the story, in service to the characters and the audience’s experience. It has heart, conscience, self-awareness and, most of all, wit that comes from a high concept, but is delivered in the most relatable and universal of ways. It doesn’t tack on a cheap, easily happy ending—instead, there is a purposeful vagueness as to what will come of the relationship between Michael and Julie. And, in perhaps the most telling moment of the film, the power has shifted from Michael to Julie, Michael is left redeemed and humble, and we are left satisfied.

There is no film that delivers exactly everything it promises to like Tootsie does. Not only does it stand on a foundation of acting, writing and directing that can hold their own with any other film of its generation or any other, but it has the added, exceptional element of being one of the funniest films ever made. That is a magical combination that is rare, and one that should be treasured, adored, praised and celebrated. Hopefully, more than once every forty years.

Tootsie was released by Paramount Pictures on December 17, 1982. It is currently available to stream on Hulu and buy on Amazon or rent on Prime Video.