This week on The Block, one of the male contestants dressed as a parody of Samantha Hayes for a comedy skit.

He put on a high-pitched voice, wore a dress, a bad wig and even worse makeup, and made a running gag out of continuously smearing lipstick all over his face.

Two more contestants also cross-dressed, one portraying judge Jason Bonham, another portraying fellow contestant Amy. I still haven't quite figured out why, except that for some reason, cross-dressing is inherently funny to a lot of people.

Ben reapplies his lipstick during The Block's Block Stars. Photo / Three
Ben reapplies his lipstick during The Block's Block Stars. Photo / Three

Agni merely had to walk on stage in a wig and he got laughs before he'd even cracked a joke. He said he and his teammate Claire were willing to go all in - "even if it means we look like absolute muppets".

Ben elicited similar laughter with his portrayal of Sam Hayes, which wasn't even remotely like Sam Hayes at all.

So why is it we think cross-dressing - and in particular men dressing as women - is so funny?

It happens all the time in comedy and pop culture. It also happens every time Halloween or the Rugby Sevens rolls around. There are even those Keep NZ Beautiful ads - and indeed, an entire campaign - in which David Fane is dressed as a woman to depict "Mama Nature" for literally no reason at all.

As far as I can tell, it's because men think women are a joke. Or men taking on feminine traits is a joke. Or trans identities are a joke. Or cross-dressing. Or effeminate men.
Is it one or all of the above? I don't know. But I'm not laughing.

David Fane as Mama Nature for Keep New Zealand Beautiful. Photo /
David Fane as Mama Nature for Keep New Zealand Beautiful. Photo /

I can hear the PC-Gone-Mad brigade firing up their keyboards already and honestly, I questioned myself writing this thinking, do I just need to lighten up?

Then I saw a story about a boy in Denver named Jamel Myles, who came out as gay and said he wanted to present as more feminine. After this revelation, he started fourth grade (year six) and made it all of four days before the bullying led him to take his own life. He was nine.

His is not the first story like this, nor will it be the last.


Cross-dressing for comedy may seem harmless, but for a whole community, it's not. If we are taught to laugh at men dressed as women, how the hell is that supposed to make the trans community feel?

If we're taught that men taking on feminine traits is funny and silly, how are they supposed to feel about themselves if they identify as more feminine? And if we're taught that femininity is an inherent butt of a joke, how are women and young girls supposed to feel about themselves?

Cross-dressing comedy makes femininity bad and masculinity good. People will laugh at and encourage a cross-dressing man on a stage because they know he will "go back to normal". But they'll mock and torture a trans woman because her normal isn't the same as theirs.

If you are trans, gender fluid, non-binary or enjoy cross-dressing, comedy is teaching you that is not normal and that you are a joke. This is where the immense pressure comes from for non-cis, non-binary people to "pass" convincingly, and lives have ended over a perceived "failure" to do so.

It also puts even more pressure on women to look a certain way. Athletes like Valerie Adams and Serena Williams are subject to scrutiny because of their broad shoulders and muscled bodies, and "butch" women are presented as either jokes or villains in popular culture.

They're mocked because a muscled body in a dress can't be a strong, talented woman - it must be a man having a laugh.

And on the other side of that, men's portrayals of women almost always play on stereotypes of women being narcissistic, superficial, vapid and needy.

There are exceptions. Drag feels different because it gives queer - and straight - men an outlet to not only explore but exaggerate their feminine side safely and freely. It's a celebration of the most extreme forms of femininity rather than a mockery of it.

And sometimes, if cross-dressing is part of the joke rather than the butt of it, that style of comedy can work - like Kate McKinnon's Justin Bieber which parodies a character rather than a gender.

But more often than not, that's not the case. And when you make a running joke out of someone looking or acting a certain way, everyone who looks, acts or even identifies with that, is hurt in the process.

Where to get help:

Lifeline: 0800 543 354 (available 24/7)
Suicide Crisis Helpline: 0508 828 865 (0508 TAUTOKO) (available 24/7)
Youth services: (06) 3555 906
Youthline: 0800 376 633
Kidsline: 0800 543 754 (available 24/7)
Whatsup: 0800 942 8787 (1pm to 11pm)
The Word
Depression helpline: 0800 111 757 (available 24/7)
Rainbow Youth: (09) 376 4155
CASPER Suicide Prevention
If it is an emergency and you feel like you or someone else is at risk, call 111.