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Are Cross-Dressing Comedies Dead?

Okay, hear me out. This is important for writers…

According to the AFI, the two greatest comedies of all time are Some Like It Hot, and Tootsie – BOTH employing the conceit of straight men dressing as women in order to achieve some advantage. Add to that list Bosom Buddies, Mrs. Doubtfire, Klinger from MASH, and the incomparable Bugs Bunny, and you have a wealth of comic material.

It now seems to be a depleted resource.

In an age when former athletes (Bruce Jenner) and traitors (Bradley Manning) are self-identifying  as women, as genders and their roles are being augmented, redefined, and outright muddied, where does the comic truth lie?

You see, whether we create comedy based on the collision of social codes – behaviors, norms, expectations – and/or with a “comic gap”  – the difference between who the character thinks he is vs who he really is – you need a strong collision, that strong gap.

We used to have strong gender roles, inequalities and really disparate expectations that would make the other sex cry if they had to perform them (ahem, comedy).

We want to laugh at swaggering dudes forced to balance in high heels, forced to be demure and all that. Then you add the sexual tension and fear of getting caught and you have a great comic engine.

But it dawned on me while rewatching Some Like It Hot the other day: we can’t remake this movie.

Some Like It Hot

Now, it’s a Billy Wilder – and considered the greatest comedy ever – so yes, it would be stupid to remake it anyway, but for today’s comic writers, it can’t be done.Cross Dressing Comedies are Dead

Yes, we can still write a tale of two unlucky guys running from Chicago mobsters. Yes, watching men try to put over on the other women in the band is amusing, but the real comic engine comes from their mores.

These are two cool lady’s men musicians known for romancing women for money. Joe does it right on camera in the agent’s office. Jerry, while not as studly, still thinks he’s a kid in the candy store of sexual mischief on the train.

So they have to be dropped: they need to have the script – those codes I mentioned – flipped on them.

First, Sugar (Marilyn Monroe) innocently climbs into his bunk. Jerry thinks he’s getting lucky at first, but then the other girls show up and it becomes a party in Jerry’s bunk.  He’s packed in, wall-to-wall women and any “surprise” will not only be embarrassing and unsexy, but he and Joe will get thrown off the train (and subsequently killed).

So Jerry’s sexual candy shop has become a terror, and once the girls put ice down his back, Jerry can only pull the emergency cord to prevent disaster.

Later, Jerry is pursued by dirty-old man Osgood, and Joe by the bellhop.

Try to tell any of those scenes with a transsexual in today’s political climate.

Can’t be done. So what if “Finkle is Einhorn?” The girl band, and the general audience don’t care. The obstacles necessary to make the scenes hilarious are gone.

Jerry could pull a Crying Game on Osgood and we’d yawn. It’s just another dude in drag.


Tootsie has to be the best cross-dressing comedy ever because it delves directly into the central of sexual politics in dating, cultural expectations in the workplace, and feminism.Tootsie - Greatest Cross-Dressing Comedy

By being a woman, Michael becomes a better man… AND shows countless other women how to stand up for themselves.

And it’s laugh-out-loud funny.

Now show me any Dorothy scene where a transgender character makes that funny. Or any scene where a straight Michael getting caught causes any consequence as it did then.

The shame is gone. Dame Edna or Rupaul could strut through and the jokes would just lay there.

Some may say that’s a good thing, culturally, but for writing comedy, it’s terrible.

We Need to Mourn the Dear Departed Values

Years ago I saw “We’re Not Married,” (also with Marilyn Monroe!) about a group of couples who discover that the Justice of the Peace who performed their wedding wasn’t yet authorized.

That meant that the couples had to race to get hitched legally before anyone found out or they were living in sin! And it gave some couples a second chance to second guess their options.

It’s was cute premise worth remaking until I realized it would never work. The stigma of shacking up outside of marriage is gone. Divorce is simple. Abandoning your spouse is unfortunately common.

In other words, today there’s no dramatic tension for this set up. We’re playing tennis without a net.

Is the same true of cross-dressing comedies?

What About The Major and the Minor?

Billy Wilder’s Hollywood debut as director was The Major and the Minor, about a sassy woman who pretends to be just shy of 12-years-old in order to get half fare on a train ride home.Nearsightedness in Cross Dressing

This twist on the cross-dress works the same way: the character uses the disguise for a specific advantage, and then realizes it’s not only hard to remove without getting in trouble, but it also harms others. The character must go through a series of comic nightmares before realizing that only truth (and the grace of others) can set us free.

Here, the Major takes in this child alone (and feigning sickness) on the train. If anyone discovers she’s “of age,” she’s thrown off the train (low risk) but the scandal would end both his career and his relationship with his fiancé.

So Susan Applegate must play Sue-Sue through a series of comic nightmares until… well, until Billy Wilder shoehorns the Major’s desire to join the fight overseas.

The movie was too stuck in WWII patriotism, so it’s ripe for a remake.

But how?

Developing a Cross-Dressing Comedy

First, find a part of the sex/dating game worthy of mockery.

Today I think the target may be tuned-out men. Failure to Launch wasn’t big, and didn’t really express today’s kind of porn and videogame obsessed sloth uninterested in dating and marriage.

These guys TRULY need a romcom.  Or a thriller/comedy / road picture that isn’t a boring mood piece about finding yourself among transgender parents or children (please, Hollywood, stop).

Say a woman disguises herself as a man in order to marry this sloth…

Wait, why? Why would she bother?  Yes, she’ll be alone but she’ll have her dignity!

And where’s the plot? What are the stakes? What social mores are we playing with? The audience experiences more interesting scenes than we could generate off that premise.

So, what if the sloth dresses up as a woman in order to get into a kinky threesome he’s always dreamt about?  Okay, that’s a porn scenario. Not going there.

Would he dress for housing like in Bosom Buddies?  Not if he’s living at home. Or on public assistance.

Hey, what if he puts on a dress in order to keep receiving public assistance!  That’s it! Our sloth discovers that married men or women get more money or benefits (gotta research that) so he disguises himself as his own wife (a la Mrs. Doubtfire)…

Well, that’s a comic premise, but is that a journey the audience wants to explore? There’s no strong anatgonist to push him forward. And where’s the development that would take him from sloth to a responsible adult ready for marriage?

So forget the sloth! Say it’s a rock star cad like Brando. What’s he against? “Whatta you got?”

What compels his journey when he has willing women, and no social mores, morality, obstacles or even shame?

On the other end of that rainbow, isn’t monogamy overrated and marriage destined to fail? I heard the failure rate’s over 50% now.

Wait, is marriage itself moribund?  Is that next to fall? Or has it fallen and I haven’t noticed?

Dammit, is there anything left with which to make a decently subversive cross-dressing comedy that ends in some positive catharsis, reaffirming God-fearing American values – whatever the hell those are?

Society, get your collective you-know-what together so we can start mocking you again. Geez, give us something to work with here.

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