Often because it’s so taboo that since (in pretty everything the other side of the 1990’s) the man is clearly not gay, it signals a new level of absurdity in the plot.

Because they don’t know how to act as a woman. And because it’s unusual to see a comedian in this way.

It’s funny because it’s sometimes mocking the other gender, or it’s just not normal. Men usually do not wear dresses. It’s unusual, so it’s funny I guess. i personally think somebody dressed up as a large fruit would be more funny than a man in a dress

English men put on a dress whenever they can get away with it….. but then we’re a strange bunch.

I think its funny if they are hairy. Then it shows you what women can look like if razors where never invented.

I can remember when there were “all girl” shows done to raise money for certain charities (usually local) in which all the cast were actually men. It was funny because they were unaccustomed to wearing dresses, high heels and all the other things generally associated with female attire. They were wobbly, hairy, muscular (for the most part), and not the least bit feminine.

Thre’s definitely something sexist about it because a woman in man’s dress isn’t seen as so ludicrous, but I can’t put my finger on exactly what.

Incongruity does the trick nicely.

Because usually they haven’t shaved their legs LOLL

And they can’t walk in heels properly!!

There are many countries where men where what would be considered dresses here. Arabic countries and South and Southeast Asian countries, for example.

Here, feminine dresses are so stylized and have become such a big part of haute couture and very much designed to enhance the shape of the feminine body (and quite a body that is, if I may say so) and the feminine body only. Men look absurd in such dress. It fits all wrong. Essentially it is a clown outfit on a man. So of course we laugh. We’re supposed to laugh.

It don’t hang right.We don’t or rather we do have the necessary equipment to carry it off.An unsightly bulge wouldn’t do at royal ascot don’t you know.

@ucme I would’ve thought a flowy dress could hide the bulge better than any pants or shorts. Unless you mean when the dress blows up in the wind. Then you could get the more structured, fitted type.

@wundayatta Yes you have described it perfectly!

It emphasizes how different a man’s frame is compared to a woman; broader shoulders and narrower hips . And in some strange way it makes them appear MORE masculine, because the dress accentuates everything that ISNT female, because we are so accustomed to seeing women in dresses.

The worrying thing is that some men look BETTER in dresses than women…..

hahaha although once I was at my local gay bar and there was this HUGE guy (big and tall) wearing a yellow floral maxi dress. It was the most HILARIOUS thing you have ever seen….He obviously didn’t come equipped with the “gay fashion sense” gene.

The classic little black dress is the look i’d be after.Goes a treat with anything.Spoilt only by the aformentioned ugly bump below stairs.Anyway I digress.

Who knows, maybe accentuation of the bulge downstairs will be the next hottest trend for men. I mean women have been making their breasts larger and more pronounced for years. It’s only a matter of time before men start showing off and enhancing their southerly regions.
Oh wait I think the skinny leg jeans are already starting it…

@HTDC you should check out “www.aussiebum.com.au”....it has jocks and swim wear for men that do just that.

The company is worth absolute millions these days…

I’m all for the mankini, waxed of course.I’d stroll around town in one of those babies.

That’s the spirit!

@j0ey Haha wow, I wonder if they’ll start marketing overseas.

A lot of humor is based on the reversal of status roles. When high status characters in a story are treated as if they were low status characters, it is funny. The inherent high status of men in our male-dominated society results in humor when a man dresses like a woman. That is why it isn’t funny when women dress like men. In fact, women in drag are often viewed as threatening. The fact that we are seeing fewer and fewer comedians in dresses suggests that our society is becoming more and more gender-equal.

@stump I think you’ve got what I was reaching for.

@janbb Happy to help

@janbb Now that’s a double entendre if I’ve ever seen one. ;)

Because it is. Hairy chest, hairy legs. Facial hair.

Wobbly on the heels. Smoking a cigar. Funny!

@j0ey That’s an interesting site that you posted there. I can see why they’re worth millions. :)

yummeh

But it’s not always that the man is tall and muscley and hairy. My brothers go to an all-boys school, and in nearly every school production there are boys dressed as women. This is automatically hilarious, even if they’re trying to do it seriously. Yet I went to an all-girls school and when we had students dressed up as men in shows that part is nowhere near as funny.

I saw a production of As You Like It where one of the minor characters, I forget who, was a man dressed as a woman. This garnered by far the greatest audience reaction of the whole show. It’s probably just me being elitist and snobbish, but I felt that this was just a cheap grab for laughs, upstaging the fantastic dramatic irony of Rosalind’s situation (for the unfamiliar, she is a girl dressed as a boy pretending to be a girl).

I don’t get what’s so entertaining about female impersonators either. Glitz and glamour and great songs and cheesy dancing is great, but I don’t think the main drawcard should be that these men look just like women.

@HTDC That was hilarious and I needed a laugh this morning!

@janbb :-)

Incongruity is a basis for humor. What is considered funny, what is laughter, why do people laugh; These questions have been the basis of many studies. Humor is still difficult to defing. People laugh when they agree with something that is stated in a humorous way, and when they see or hear something that is incongruous. A man in a dress is an incongruity in our society. Even now.

Because it’s awkward, and people find awkward hilarious.

It’s even more hilarious if he wears a conehead hat.

How many crossdressers does it take to change a light bulb ? Three. One crossdresser to go up the ladder, one crossdresser to watch for ladders, and one crossdresser to paint the bulb pink with pretty yellow dots.

.

Because it just is. The male performers who dress like women are not always funny, just unbelievable. Women’s clothing fashion shows using male (unprofessional) models are always hysterical; we’ve raised a lot of money that way.

Nothing other than people’s unease with non-normative gender expression.