By the time I was in middle-school I was already a dopey romantic. I spent too many hours to admit crafting not one, but TWO, mixtapes (as in cheapo, plastic, 90 min. Memorex ca-settes) made up entirely of 1980s hair metal power ballads. Every rose has its thorn, Bret Michaels, PREACH! I’m not sure what I intended to do with those tapes. I think I had some vague notion of tricking the cute boy I liked, the one with the Buddy Holly glasses and longish hair who also happened to be a devout ACDC fan (Not that I made it my business to learn every rancid word to every ACDC song I could stand. No), into sitting on the couch with me on a Friday night. In this scenario we would listen to these songs laced with angst and pedal distortion about love that lasted forever (until it didn’t because she died or he cheated or went to jail or found out they were related) and the message would seep into his subconscious that I was the girl for him. Instead, what I actually did was hang out in my parents’ finished basement, flipping these tapes over and over late into the summer night while I worked on my super keen oil paint-by-number craft set. Social Life Level—crushing it.
It was an easy hop from music to movies. I have yet to meet a Romcom I would pass by and the 1980s were lousy with them—Moonstruck, Roxanne, Sixteen Candles, Say Anything, Arthur (because nothing says true love like alcoholism), Big, Splash. These and so many other flicks spoke to my 11-year-old self in a profound way. Even though I was the girl desperate to be gotten, to be pursued, I deeply identified with Hanks and Cusack and Martin as the earnest, sweet weirdo who wooed that seemingly unattainable person. You could be an oddball and still wind up with the person of your dreams. This felt hopeful to me on both sides of the romance fence. Life would eventually deliver its share of awkward, painful, incredibly un-Romcom-ish lashes to my tender, romantic heart. But, whatever. I still had Jon Bon Jovi who promised he’d always be there for me, like, for real.
So it was during my feverish affair with all things Romcom-ish that I eventually found Tootsie. I was probably twelve when I first saw Tootsie. I checked it out of the library (nerd) on a dodgy VHS tape (old nerd). What initially sparked my interest in the movie was not its plot, but my blossoming obsession with all things Bill Murray, who plays a supporting, yet wickedly comic role as the best friend and roommate of the main character played by Dustin Hoffman. I came for the Murray (who did not disappoint), but I stayed for the goofy romance.
The film’s main title theme, “It Might Be You” further cemented my adoration for this flick. Performed by Stephen Bishop, the song is a suspended swoon into the realization that the person you’ve been searching for all this time has been right here all along. It’s genius. It contains a lovely, lilting melody spun from pure sugar that simply begs to be the first dance at your wedding. Additionally, it neatly sums up the plot of every romantic comedy in the history of romantic comedies that we also secretly wish were just a wee bit closer to real life. I remember listening to the song play over the closing credits, watching to see who had written this tune that was TELLING ME MY LIFE. And because the Internet was waiting to be discovered by Mark Zuckerberg, I had to ask my mother to drive me to the local record store, Strawberry’s Tapes & Records, to hunt down the soundtrack.*
The tale of Tootsie is as follows: Dustin Hoffman stars as Michael Dorsey a struggling New York actor who dresses in drag to pass himself off as “Dorothy Michaels” in order to get a part on a soap opera because GENDER. He ends up falling for his co-star, played by the savagely sly Jessica Lange because COMPLICATIONS. Add in the brilliant Bill Murray as Jeff Slater, Dorsey’s roommate who is also a struggling playwright; the delightfully ditzy Teri Garr as Sandy, Dorsey’s friend and possible romantic interest; and Dabney Coleman as a smarmy TV producer and the whole thing practically writes itself. Dorsey’s masquerade as “Dorothy” leads to all kinds of farcical shenanigans that reach a hilarious tipping point. Hoffman is Hoffman—the man could win an Oscar portraying a paper bag left out in the rain. By the end of the film it’s completely believable that his character could wind up with a fox like Jessica Lange, again, giving hope to the rest of us slightly left-of-center types.
Fast forward to Chicago where I’m in a PhD program studying theatre and gender (14th Century Malaysian Poetry was all full, had to go with something less practical). In a seminar we’re talking about performers who work in drag. Someone brings up Tootsie. “Something’s telling me it might be you…” I can barely stop myself from humming the chorus softly under my breath (Damn you, Stephen Bishop you Pavolvian devil!). I haven’t seen the flick in upwards of fifteen years, but just the mention of it gives me that squishy feeling in the cave of my stomach. It’s the same feeling you get when you see an old flame after the wounds have scabbed over and all that remains is that sweet familiarity, the inside jokes, the smell of their hair on your pillow.
Tootsie leads to a meaty seminar discussion about the politics of performance, about gender and feminism and the culture wars of the 1980s, about the appropriation of female identity and other fifty-cent phrases and ten dollar theories that I can sling with the best of them because INTELLECTUALISM. I take it seriously, I do, and I’m invested in wringing the significance out of this conversation. But I already know I’m going to stop in at the Blockbuster a few streets from my apartment on my way home from campus tonight and have a date with an old friend.
I watch it and it’s everything that made me smitten when I was a kid. With a greater appreciation of wit and comic timing, a lot of the writing is far funnier than I remember. There’s a reason why Hoffman, Lange, Murray, and Garr are giants in their field—their performances are so strong, nothing feels dated or hacky. But there is something different with this viewing. For the first time, I pay more attention to the opening sequence of the film and it hits me—this isn’t a movie about pursuing who you love, it’s a movie about pursuing what you love.
The movie opens with a montage of Michael Dorsey doing what he does best: acting. We see him rehearsing plays, leading workshops, and going to (mostly failed) auditions. Each time there is a cut back to Michael conducting a workshop we hear him telling his fellow actors things like: “What do you care more about than working?;” “There’s no excuse for not working. There’s no excuse. There’s unemployment;” “You’re an actor, you’re in New York. There is no work. But you gotta find ways to work.”
Just after this sequence, we see Michael and his roommate, Jeff, (Bill Murray) working at a Manhattan restaurant. This establishes the quintessential every-waiter-is-an-actor trope. Jeff tells Michael about the rewrites he’s done to his new play, Return to Love Canal. Michael promises Jeff they’ll work on it later that night at home. Except it happens to be Michael’s birthday. When they arrive at their apartment there is a house full of people waiting to surprise him. Over the course of the party scene we see Michael talking to people, but mostly obsessing over his career, over the work. He tells one friend about Jeff’s play: “The point is Sandy and I are raising money to do Jeff’s play in Syracuse. We’re going to do it. You could do the same. In the Poconos. You’re sitting around saying ‘I can’t work,’ create your own—you make it. You find a way to raise it.” He is so singularly focused on this line of thought that he hardly notices Sandy (Terri Garr) sashay over to him carrying someone’s baby, cooing at Michael to look at this adorable lump of love. The subtext is unmissable–she lives in a world where people get married and have babies; he lives in a world where there is “work and unemployment.”
It hits me: This is the spine of the movie.
The next day Michael finds out that a Broadway role he was supposed to audition for already went to another, in his opinion, extremely less talented actor. Furious, he storms into his agent’s, George Fields (played by Sydney Pollack), office. He confronts George who is forced to tell Michael that he’s essentially a “nobody” in the business. It’s not because he doesn’t have talent, George explains, it’s because he’s a tyrant to the craft, a perfectionist who prizes the art above all else. Michael brings up Jeff’s play–a great play, a masterpiece even that Michael intends to star in. His agent laughs at him. “No one wants to see a play about a couple living next to nuclear waste. They can see that in New Jersey!” (Like I said–a much greater appreciation for fine comedy writing).
“I don’t want to argue about it,” Michael says. “I’m going to raise the money and produce Jeff’s play. Set me up for anything.” That’s when George tells him that he’s essentially unemployable. He’s too difficult, too much work, even to shoot a 30-second dog food commercial. No one in New York or Hollywood will take him on.
“You are a wonderful actor,” George says. “But you’re too much trouble. Get some therapy.”
“Okay, thanks,” Michael replies. “I’m going to raise the money to do Jeff’s play.”
The drag, the gender bending, the comedy of watching Dustin Hoffman wrestle with a bra, and even the silly awkwardness of witnessing him disguised as a woman trying to control his crush on Jessica Lange is all window dressing for what really drives the story: staying true to your passions, committing to the work, serving your art.
As someone who does creative work, I really connect with this message. Writing is not just fucking hard (duh), it’s often a lonely strange pursuit that requires a bottomless supply of grit, resilience, and faith. It also has my heart and soul in a full nelson the way acting possessed Hoffman’s Michael Dorsey. I hear Dorsey’s voice in my head: No one “reads” anymore, print is dying, long prose is anathema. Yet you’re a writer. What do you do? You write. You find places to publish or you make your own. There’s no excuse. There’s only not writing.
When I feel like I’m throwing pebbles into the Grand Canyon, when I’m letting myself get pulled down under the current of the “Who would want this? Who would read this? What are you doing with your life?” thoughts, I reach for Michael Dorsey’s mantra. “I’m going to raise the money and do Jeff’s play,” I say, sometimes out loud. It’s shorthand for refusing to give up, for believing in myself even if no one else does, for recommitting to what this art is, what it means to me, and what I know it can do in the world.
At the end of the movie, Michael’s gender adventure costs him relationships, a lucrative, but artistically bankrupt job on a hit soap opera, and nearly the girl. Spoiler, he does get her. He and Jessica Lange have a tentative and sweet reconciliation on a New York street corner. When I was twelve, this ending was immensely reassuring. The Laws of Romcom upheld! But after watching the movie years later through a different lens, I found I barely noticed the charming period to the end of their story. For me, the real resolution happens in a shot that takes place a few scenes before the actual ending. The camera pans over a theatre marquis that reads: “Return to Love Canal, a new play by Jeff Slater.” You find a way. You make your way. You roll, Tootsie, and you keep on rolling.
*Strawberry’s Tapes & Records did not have the Tootsie soundtrack because it was 1987 and the movie was already considered paleolithic by retail standards. I eventually secured my prize through the Columbia House mail order tape and record scam..er club.