Wednesday, June 11, 2014



A fellow went out on a bender
And woke up with his briefs in the blender
He turned off the lights
Pulled on his wife’s tights
And now feels more fluid in gender

These shoes are not being sensible.

What follows is probably gonna make a few folks pissed. I hereby apologize in advance to those who experience any panty bunching while reading this particular post. I’m just thinkin’ out loud, Peeps.

So here’s the thing. There’s a long history of humorous cross-dressing and “drag” as comedy. Classic stuff. From ancient times, through all of vaudeville, to Bugs Bunny and good ol’ Uncle Miltie, to Bosom Buddies, to Klinger in M*A*S*H and well beyond. In fact my wife attended an Ivy League school that has a long tradition of ending every variety show with a Can-can style kick-line composed entirely of beskirted males. I’ve seen it at reunions and it’s a blast. Always hilarious. The point is I’ve laughed at this kinda stuff repeatedly over the years and have many friends in show biz (and out) who partook and still partake.

Hell, I’m even capitalizing on it with this post’s illustration.

All in good fun, and so forth.

But here’s what I think, when I think. There’s something deeply wrong underlying it. Why exactly do we find it hilarious when a guy dresses up as a woman?

Why isn’t it funny the other way around? When Marlene Dietrich wore top hat and tails it wasn’t silly, it was erotic. When Janelle Monáe performs in a suit & tie, it’s way hot. Face it, even “Mary Poppins” (Julie Andrews) in Victor Victoria was rockin’ the dude-wear. If some woman in a perfume ad wakes up and slips into nothing but her man’s dress shirt? Super sexy. Some man in a cologne ad shrugs on his lady’s frilly blouse? Not so much.

And, frankly, it often feels like there’s something deeply demeaning toward women when a male performer gets laughs simply by dressing himself up as a female.

Brace yourself because I’m about to make a really disturbing analogy. But I think it’s at least semi-valid. Here goes. Minstrel shows. We don’t allow them any more, thank God. Yet for years white male performers regularly dressed up as African Americans – a brutally oppressed, beaten-down group. They’d doll themselves up in the clichéd trappings of that group and prance about pretending to be a part of that “jolly” exploited underclass for our entertainment. They exaggerated every supposed characteristic folks of the time believed about people of color: shuffling walks, wacky patterns of speech, banjoes, watermelons, wild hair, massive lips, and blacker-than-blackface. “Look how silly and goofy them folks are! Ain’t it funny when I, a white male, pretend to be one?”

We all, hopefully, get how obscene and wrong that is now. But somehow it’s still okay nowadays for random gents to entertain the crowd by adopting exaggerated versions of all the stuff our society currently thinks of as “female.” These men pretend to be women (which – ahem – also happens to be an oppressed group, not coincidentally) by wearing gaudy dresses, overstuffed bras, huge wigs, fishnet stockings, gigundo eyelashes, and tons of ladled-on lipstick, all while teetering about on high heels, clutching handbags, and squealing in high-pitched voices. “Look how silly and goofy them women are! Ain’t it funny when I, a male, pretend to be one?”

Really creepy, when you think about it.

Dietrich Does Drag. Because Damn.
Okay, so maybe I went off a bit on a tangent there with my minstrel show analogy. Harsh, but I feel it’s legit, at least on some level. I do, however, realize that some modern drag shows, particularly non-comedic ones performed by yet another oppressed group (gay men), can sometimes be more of a respectful celebration of “classic old-Hollywood feminine glamour” than an attempt to belittle and demean women.  Understood.

Oh, and speaking of non-comedic drag that works, last summer I saw an amazing production of Richard III at the New Globe in London where, just as it was originally done, men played every role, male and female. It was subtle, beautiful, and brilliant.


Looks like I not only lost my train of thought there, but then missed the following train and was forced to take a cab home.


Okay. I’m back. My real point is: the clothing we as a society dress our daughters in is stuff we find hilarious when our sons wear, but not the other way around. And that’s fundamentally wrong.

I think it’s all tied in with how it’s still considered an insult to call a boy a “girl,” how a slang word for female genitals is still used in the locker room to call a dude “weak & cowardly,” and how it continues to be cruel to suggest a guy “runs like a girl,” etc.  Girl-ness is still thought of as intrinsically inferior. Frivolous. And silly.

And therefore, when a guy pretends to be one, it’s funny. Ha ha ha.

Bottom line time. As a life-long feminist, I have to say that I feel like we will not have achieved true equality until the day comes when either women have largely stopped wearing the kinds of clothing that we find “hilarious” when men put on, or the day our attitudes toward so-called “girly” clothing has changed enough so it’s no longer funny for either sex to wear it. (The latter would be preferable because it’d suggest we’d’ve become a more accepting society in all gender directions.)

And with that (clumsily) expressed, this particular fellow who is (in spite of a last name that implies otherwise) of mostly Scottish descent, will straighten the pleats in his kilt, adjust his undersized sporran, and sashay off into the daughterset.


  1. I agree with most of what you say. But as a straight man brought up in the American culture it's hard to let go of a lifetime of sex-role indoctrination. Yes, my consciousness has been raised enough over the years that I realize women’s fashion can be oppressive, impractical, stupid, and restrictive. But, that being said, a beautiful woman in stiletto heels, red lipstick, pushup bra, and a tight lacy dress still gets Mini Me excited, even though in my bigger head I know it’s not PC.

    1. Thanks for the comment. And I hear you. I’d probably have the same reaction to a woman in that kinda outfit. I’ve honestly got no problem with that. What turns you on is what turns you on -- whether it’s a rubber ballgag, chainmail codpiece, honeybadger costume, or high heels. It’s when our society, in essence, insists that women walk around all day wearing said ballgag that I have a problem… :-)

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  3. High heels are bad for you and they hurt. We've been brainwashed into thinking they are sexy. I protest. There, I said it.

    And I'm taking my ballgag off, too.

  4. Cross dressing is denigrating to women? Hmmm. I’ll have to think about that one. It seems more denigrating to the comedian (a long-held form of comedy, in and of itself) to pretend they are the opposite sex. The comedian cross-dresser has never seemed that funny to me, but rather awkward. Since they don’t seem that funny to me, I can only guess why there is a long tradition of cross-dressing comedians. I always assumed that the humor was because the man was obviously not being a very good woman, with a beer gut and a beard, and the fake high-pitched voice is funny because, again, they were so obviously bad at it. I would imagine the more feminine the comedian, the less funny the cross dressing would be. And part of it is that the comedian thinks they’re being funny. As you pointed out, if they were serious about cross-dressing, like a serious drag queen, no one would be laughing.

    I would be surprised if people thought it was funny because women are goofy, but rather because the comedian seemed goofy trying to be a woman. It seems more like a comedian pretending they are an Olympic athlete, or a politician, or a psychiatrist, when they are obviously really bad versions of those people.

    Why aren’t women thought of as funny when they dress as guys? Well, in my view they can be. Lucille Ball seemed pretty funny when she did it, but again, she wanted to be funny. If she wanted to be sexy dressed up as a guy, she could have been that, too.

    Once again, I am impressed with your mind, Stoney. Thanks for making us think about this.

    (Just a bit more) It also depends on *how* the comedian portrays a woman. If they're acting like an idiot, then that is denigrating to women, or at least the woman they are portraying. If they are trying to act like a real woman and failing, then that is more denigrating to themselves. The blackface comedian usually acted like an idiot, so it was obviously a denigrating act of comedy.

    1. Andy, many good points! Thanks for your thoughtful response. Great stuff.

      I still say that this basic, simple fact is telling: Take any woman who is considered pretty universally attractive, say Megan Fox or Marilyn Monroe. Put her in a tuxedo or man’s business suit. Hot. Now take any male considered pretty universally attractive. Say Ryan Gosling or Sean Connery. Put him in an evening gown or cocktail dress. People will laugh. This, to me, is not a trivial thing.

    2. Also, your point at the end about the “intention” behind the drag is a good one, as is the comment about minstrel performers acting idiotic.

      But, devils advocate: it could be argued that when Al Jolson put on blackface and took a knee to sing “Mammy” he did it with great pathos and dignity and respect for the character he was portraying. Yet we still cringe when we watch it today. Why is that?

      I think it has something to do with what them young-uns today call “Privilege.” In this still very racist/sexist world, being a white male and pretending to be someone of lower privilege just feels inherently wrong and insulting.

      But again, this is all just me thinking out loud.

  5. I’m not sure I’d put drag shows on the same level as minstrel shows (I almost wrote menstrual shows by mistake), but it’s an interesting thought experiment.

    Your other point, about boys’ and girls’ clothing in general, I’m totally with you on. Perhaps when a “first class citizen” dons the costume of a “second class citizen” we find it inherently funny. If both genders were truly equal, we probably wouldn’t find Sean Connery in a well-fitted, stylish evening gown automatically silly. But in our society as it stands, a woman putting on male clothing is putting on the wardrobe of power and privilege. A man putting on women’s clothing is putting on the garb that still, even today, signals fragility, weakness, and lower status.

    BTW, this is probably why I always feel a hot chick (pardon the expression) clomping around in army boots is sexier than one teetering about precariously on high heels.

    -- Barry Evans

    1. Thanks for the comment, Barry! Good stuff. In fairness, though I agree Connery would look pretty silly in an evening gown, I think you would rock it.

  6. Well, we'll, well. Ev-a-bottie has so much to say about this. Sean and I think you kids, male female, and all the in between denominations should just settle down now, put on your big red diapers and catch a ride in the big rock head in the sky. P. S. Your illustration style is superb and captures your sense of humor so perfectly. Love it! Love it all! You can wear any thing you like my Scotty-boieeeee!

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  8. I guess we can intellectualise the whole thing but I find it hysterical when men dress as women (some like it hot, dame edna) and I dont really see the comparison to minstrel shows...

    1. Hi Stoney, its me, Lesli (LB) its all good food for thought... xoxo

    2. Thanks again for commenting, Lesli! (And I also love Dame Edna and Some Like it Hot.) ;-)

  9. It seems like a good indicator would be if women are offended by men dressing as women for comedy. What do you think, women?

  10. And by-the-way, I don't have any skin in the game either way, especially because I don't really like that kind of humor anyway. If I learn through this conversation that men dressing as women for comedy is denigrating to them, then I'll be the first one (or more accurately, the next one) to boycott. But I don't really see it. I'm actually looking forward to being enlightened, though, so I hope some more women jump into the discussion.

    1. You’re right that we should hear from women on this issue. Incidentally, my wife read the post and tells me she wholeheartedly agrees with me about it all… but then again she also tells me I’m not getting fat or going bald and that I’m amazing in bed. None of which is true.

      I meant it when I started the original post by announcing that I was “just thinking aloud.” It’s mostly just an interesting mental exercise. But, to address your point about how woman pretending to be men can indeed be funny. I agree. I didn’t mean to imply a woman could never, ever be funny by dressing up as a man. Sure they can. (The link you sent me of Sarah Silverman in a mustache is a perfect case in point.) But, to belabor my gender/race analogy, when Eddie Murphy and the Wayan Brothers put on white face and act all “whitey,” they are indeed often very, very funny. But does that mean blackface is okay to do then? Not a bit.

      The semi-coherent point I’ve tried to raise here is, I think, related to that old saying about how humor ideally should always “punch upwards,” toward the powerful and privileged.

      Thank you again for all your thought-provoking comments. I really appreciate them!

  11. Men are considered handsome real humans who can add silly padding, uncomfortable shoes, clothes, and makeup, and screech in high voices to be those embarrassing less than human jokes, i.e. women. Without the makeup and clothes, women are seen as lesser men, not even useful enough to be successfully regarded as their only accepted roles in society: decorative wallpaper or nurturing mommies. Whether the penis goes in or the baby comes out, women are seen as worthless other than their holes.