When Jack Lemmon Snatched All the Wigs in “Some Like It Hot”

In this 1959 drag race, the actor sashayed away with nearly every scene, setting a new bar for gender-bending comedy.

If dying is easy and comedy’s hard, let these iconic queer film performances teach you a thing or two about schticking a difficult landing.

Hollywood has been going to the same old “man in a dress” well pretty much since the invention of film. There’s apparently no easier, cheaper way to get a laugh than by showing a pair of hairy gams peeking out from a skirt. But the problem with that joke is it’s one-note. How funny can the same gag be after you’ve seen it countless times? Well, if you’re Billy Wilder, it can be the key to just about the funniest film ever.

In 1959, Wilder directed and co-wrote, with frequent collaborator I.A.L. Diamond, the movie Some Like It Hot, a crackling Prohibition-era comedy about two jazz musicians, who, on the run from the mob, take up with an all-female band. Tony Curtis and Jack Lemmon are the two musicians in question, and Marilyn Monroe is the unwitting lead singer who complicates their rouged ruse.

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(L-R): Marilyn Monroe, Jack Lemmon, and Tony Curtis on the set of Some Like It Hot.

The film is a delight from start to finish thanks to a clever script that keeps everyone on their toes, Wilder’s deft direction that hits every beat with laser-like precision, and the endlessly engaging performances from the three leads, particularly Lemmon.

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Lemmon.

Showcasing the kind of commitment that made him both a brilliant comedic and dramatic actor, Lemmon dives into his role wig-first. He starts out as bass player Jerry, the weak-willed sidekick to Curtis’ womanizing saxophone player Joe. After the buddies accidentally witness the St. Valentine’s Day Massacre, Joe convinces Jerry to hide out with Sweet Sue and Her Society Syncopators, a traveling all-girl band that will, conveniently, get them out of town and fast.

Before we go any further, please know that Some Like It Hot requires a sustained suspension of disbelief. And not because Lemmon and Curtis are unconvincing as women. Quite the opposite. When the actors first got done up in their hair, makeup, and costumes, they walked around MGM studios to see if they could pass. After they discovered they could use the ladies’ room to fix their faces without any of the women complaining, they knew they were ready for their close-ups. Still, Wilder decided to shoot the film in black and white because the actors’ makeup gave off a greenish hue on camera.

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Monroe and Lemmon.

But as a viewer you can’t help but wonder, How did Joe and Jerry get so dolled up, and on such short notice? In truth, you’ll probably question any number of the characters’ actions, but the film’s absurdity is one of its selling points. Once you surrender to its charms, you’ll just sit back and enjoy the ride.

So with Jerry on board, he and Joe—or rather, Geraldine and Josephine—make their big debut, barreling down a train station platform in their precariously perched high heels. A male cabaret dancer [read: homosexual] named Barbette was hired to teach Curtis and Lemmon to walk in heels, but after about a week, Lemmon declined his help. He said he didn’t want to walk like a woman—he wanted to walk like a man trying to walk like a woman.

Meanwhile, by the end of the film they’re sprinting in those stilettos, proving that a good heel is the great leveler.

From the start of this drag race, it’s evident that one of the gurls is into this a lot more than the other. Joe sticks to his alias, Josephine, but Jerry decides to go by…

Because he’s always “felt” more like a Daphne. Come through, sis!

And that is where the comedy comes from—the joke isn’t so much about two dudes in dresses, but about the politics of gender. Things get so deliriously confusing with characters going back and forth between “man” and “woman,” and with unlikely romances occurring, that it elevates the whole cross-dressing trope to high art. It’s a bar that few film comedies, with the exception of Tootsie, would reach.

The perfect example of this is the relationship Daphne develops with millionaire would-be playboy Osgood Fielding III, played by veteran comedic actor Joe E. Brown. With Joe/Josephine’s prodding, Daphne strings Osgood along so that Joe—as his other alter ego, the Cary Grant–esque would-be millionaire Shell Oil Jr.—can use Osgood’s wealth and yacht to seduce Marilyn’s boozy, broken-hearted broad, Sugar Cane.

Same.

See? Deliriously confusing. But you know who’s not confused? Osgood. He immediately falls for Daphne before she even knows what’s hit her. After a romantic night, tangoing ’til dawn with Osgood, she accepts his marriage proposal. Bewitched, bothered, and bewildered, Joe asks his old pal, “Why would a guy wanna marry another guy?” To which Daphne answers, with complete sincerity:

From there, things escalate until the final scene, in which Daphne, having once again escaped the mob, this time with Osgood (and lovebirds Sugar and Joe), finally comes clean, leading to perhaps the most famous, and funniest, last line in all of film.

No, nobody’s perfect, but in Some Like It Hot, Jack Lemmon sure comes close.

Lester Fabian Brathwaite is an LA-based writer, editor, bon vivant, and all-around sassbag. He's formerly Senior Editor of Out Magazine and is currently hungry. Insta: @lefabrat