Is Crossdressing Funny? 2

Living in a different country than my parents means that on occasion I get to travel back to the motherland that is the UK and hang out with them for a bit (along with not paying for a hotel, which is quite nice). We’re a bit boring – we tend to just sit around watching TV, but then again, that’s what we always did when I lived there; sometimes I think it’s a miracle that my eyes aren’t actually rectangular.

I’ve mentioned before that I’m very open about my crossdressing. My parents know about it – I don’t think they particularly understand it, but they’re not constantly haranguing me to stop, so that’s definitely something. The only time it gets awkward, for me at least, is when we’re watching the ol’ goggle-box, and someone makes a joke referencing crossdressing or trans people. I shift around a bit, uncomfortably, hoping for the moment to pass as quickly as possible. I suppose I don’t really watch honest-to-god television anymore in the age of Netflix, so maybe this is rampant here in the US as much as I assume it is in the UK, or maybe us Brits are just a queer (choose your own definition) bunch, but it seems as if on the few occasions I’m in the UK watching TV with my parents, there happens to be a joke about crossdressing and/or trans people.

The worst part is that I’m not sure which I’m annoyed by most: The fact that we’re an easy target for jokes, or the fact that they still make me laugh, albeit guiltily now.

So why do we find things funny, anyway? There’s lots of theories about it, but the ones I find the most convincing involve surprise and the reversal of expectations. British comedian Jimmy Carr once said that a joke is like two different stories: The first one which sets up your assumptions, and the second which makes you realise your assumptions were wrong. When it comes to jokes about crossdressers, it seems like the first assumption “Men don’t <x>”, where x is usually something classically associated with women.

Don’t get me wrong – I’m of absolutely the opinion that when it comes to comedy, nothing is off-limits. That said, there are good ways and bad-ways of going about it.

(Your opinions of the following examples may be different from mine, and that’s ok)

Here are some examples of comedy which references crossdressing/trans issues:

Doctor Who – Susan the horse

Typically, I *love* Doctor Who, but this particular scene bothered me a lot. I think it’s great that trans issues are coming to the fore in popular media, but this is a horse. And this was clearly a line that was supposed to make people laugh at the fact that some people don’t necessarily jive with their assigned-at-birth gender.

“Barbara” – The League of Gentlemen

Again, The League of Gentlemen is one of my favourite shows. A lot of the show was off-the-wall, dark and peculiar humour, but throwing in an extremely manly pre-op transwoman felt mean and unnecessary.

“Work it”

I am glad this TV show didn’t get made – it seems like the only joke in this show was “Ha-ha, men in dresses. So funneh!”. That’s not to say that it couldn’t have been funny – there’s definitely some gold in those comedy veins – they just were entirely unable to find any.

I think the thing that tied all of these together was that they weren’t necessarily well thought out, and come off as derogatory and mean – or even as something that’s “other”.

And here are some examples that genuinely make me laugh:


There is literally nothing offensive here. The humour comes from the surprise of Joey doing something effeminate and having kept it a secret, and then the line at the end where Chandler is impressed at how good he is at it. Awesome.

Mrs Doubtfire

I cried when Robin Williams died, I’m not ashamed to admit. Mrs Doubtfire was an amazing movie, and I don’t think at any point did I ever feel like I as a crossdresser was made fun of. Indeed, I felt like a lot of Robin William’s scampering around as Euphagenia felt real. The difficulties with makeup and getting ready and wearing these clothes such that people perceive you differently, but being entirely the same inside. I could hardly *not* relate to that.

And curiously, this is the one that makes me laugh the most (some of you might find this one offensive)
“I’m a lady” – Little Britain

This one kills me. On the face of it, I can’t help feel that this should be offensive. But I’ve watched it three times just now and I feel like I’m going to cry with laughter. Maybe because it feels a bit close to home without being mean. For some reason, it’s surprisingly relatable. On top of that, it should be noted that the man playing Emily Howard in this clip is none other than David Walliams, writer of The Boy in The Dress, which was made into an amazing TV movie, which I reviewed extremely positively last year.

So where was I? Oh yes. Is crossdressing funny?
Absolutely, I think it is, so long as it is done with sensitivity and love. Personally, I attempt to take myself as un-seriously as possible. I’m happy to talk to, and joke with, people about crossdressing, what it entails, and what the struggles are. And I’d be thrilled to find as much humour in that as we possibly can.

But if the joke is “Look at that person! They’re different and weird!”, I’m just going to walk on by.

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2 thoughts on “Is Crossdressing Funny?

  • Ginia Love

    The first three are also just not funny….like seriously…not funny. The last one – I’m with you Duncan – cracking up!!! But I was feeling guilty for laughing. Until you shared why it makes you laugh – because you relate to it – it’s real. Funny to me comes from a place of honesty….did I spell that right? Ah shit who cares – I ain’t got time for grammer. One thing I’m grateful for is being able to laugh about how shitty living can be. Thank you for sharing and being real and I love you brother.
    Mrs. Doubtfire rocks dude!!!

  • David

    hi David here from Dublin in Ireland. I’ve been fighting a crossdress fetish all my life. Im an athletic looking male with athletic gym body. straight acting you’d never guess I was bi you’d be shocked looking at me. I’ve been dressing in private. Wig, no make up experience, with lingerie under a slutty dress. still haven’t mastered my look and am confused at times is this really what I want