Tootsie’s Crossdressing Comedy with a Heart of Gold Shouldn’t Have Worked, but It Did

It’s a 1982 comedy starring Dustin Hoffman, a movie star who wasn’t known for comedies, directed by Sydney Pollack, a filmmaker who wasn’t known for comedies. Of course, these guys butted heads throughout the production. The revolving door of screenwriters who worked on the script (which was still getting punched up during filming) is already the stuff of legend. And let’s not forget: It’s about a guy in drag. It’s a premise that’s been famously used in other classics, from Howard Hawks’ I Was a Male War Bride, where Cary Grant donned women’s clothes to get back in the U.S., to Billy Wilder’s Some Like It Hot, where Tony Curtis and Jack Lemmon pretended to be gals to get away from gangsters. Even Blake Edwards came out with a drag movie that same year, having wife Julie Andrews play a female impersonator in Victor/Victoria.

But even with all that working against it, Tootsie became a comedy classic. Not only did this $21 million budget movie become a critical and commercial hit—eventually grossing $241 million, making it the second most profitable film of 1982 (a little movie named E.T. took the top spot)—it was also nominated for ten Academy Awards, including Best Picture. People really took to the idea of Dustin Hoffman in a dress.

Fresh from starring in the Oscar-winning smash Kramer vs. Kramer (where he got his first Oscar for Best Actor), Hoffman—that quintessential Serious Actor—did a 180 and headlined this comedy, where he starred as a quintessential Serious Actor. He takes the piss out of himself as Michael Dorsey, a dedicated thespian who’s also something of a prick. (Anyone who knows about the hell he put his Kramer co-star Meryl Streep through knows how that can be painfully accurate.)

A standard-issue New York actor—auditioning during the day, waiting tables at night, teaching an acting class somewhere in-between—Dorsey’s commitment to his craft has made him a pariah in the industry. Even his own agent (Pollack, pushed into the role by Hoffman) tells him no one on both coasts wants to hire him. He eventually proves him wrong by becoming Dorothy Michaels. Covered in heels, makeup and conservative women’s wear, he lands a gig on the daytime soap opera Southwest General, where he becomes an overnight sensation.

As ludicrous as this setup is, Tootsie pulls off the amazing feat of being an absurd farce that seems plausible because Pollack, Hoffman and the cast (which also includes Teri Garr as Dorsey’s neurotic gal pal, Dabney Coleman as a sexist TV director, and a young Geena Davis as Dorsey’s rarely-clothed castmate) don’t go for broad laughs. Dorsey goes on quite the eye-opening journey as his star rises. Between becoming a close confidant to his single-mom co-star (Jessica Lange, who won a Best Supporting Actress Oscar for her performance), whom he eventually falls for, and seeing how women like her get harassed and undermined on the set, Dorsey eventually realizes how bad the fairer sex has it.

Even when things get ultra-ludicrous (yes, a couple of lovestruck dudes start pursuing Dorsey/Michaels), Pollack—who previously helmed such straight-faced dramas as They Shoot Horses, Don’t They? and Three Days of the Condor—painstakingly made sure that the audience believed his protagonist’s journey from desperate man to successful woman. “I had to find a way to make all of this humor absolutely reality-based,” Pollack says in the commentary on the Criterion Collection Blu-ray.

Despite their behind-the-scenes disagreements, both Pollack and Hoffman wanted the comedy to come out intelligently and truthfully. They brought in several screenwriters to help them make the story (originally based on Don McGuire’s play Would I Lie to You?) both funny and believable. Larry Gelbart, Elaine May, Barry Levinson and Hoffman’s late playwright pal Murray Schisgal were just some of the credited and uncredited scribes who contributed to the script. The star and the director also didn’t mind throwing in some improvised scenes. (Mostly provided by Bill Murray, assuming the audience-surrogate role as Dorsey’s playwright roommate.)

Even with all these cooks in the kitchen, Tootsie turned out to be a delicious delight. It’s the sort of sophisticated comedy people love to say is just not made anymore. But it was barely made then. In the essay that accompanies the Criterion Blu-ray, film critic Michael Sragow starts off by saying, “Tootsie is a marvel of big-studio moviemaking from an era when such a thing was no longer considered possible.” He mentions how Columbia Pictures, the movie’s distributor and the same studio that once dropped classic comedies like It Happened One Night and The Awful Truth “funded and developed it with a moxie that had mostly vanished from the majors when movies ceded ground to television and studios got sucked into conglomerates.” (Sadly, ain’t a damn thing has changed.)

Even though dudes in drag is considered a lowbrow (or, in the case of performers of color, racially demeaning) way to get laughs, cross-dressing comedies are still a far cry from going out of style. Hell, earlier this year, Tyler Perry dropped another Madea movie on Netflix. Years ago, I interviewed indie-film producer/guru John Pierson, who spent some time in Fiji running a movie theater with his family. (This was chronicled in the movie Reel Paradise.) One of the big hits at that theater was Sorority Boys, a forgettable 2002 farce about a trio of frat guys who get all dolled up and hide out at a sorority. As Pierson told me, “A man dressed as a woman—that’s a surefire laugh in Fiji, but not only in Fiji.”

Sure, drag comedies will always round up the yuks. But, unless another group of unlikely people team up to do something fresh and funny and feminine, we may never see another movie that brings the same wit, cleverness and heartfelt, honest humor as the sweet-as-hell Tootsie.

Craig D. Lindsey is a Houston-based writer. You can follow him on Twitter and Instagram at @unclecrizzle.