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ContraPoints is the hilarious YouTuber delivering hardcore politics in drag

We talk to the video star about trolls, newfound fame, and what’s going to happen to the people that hate trans women

If ContraPoints had been as massive in 2016 as she is now, things would have been different for me. You see, in 2016, I had the most dismal one night stand of my life. His name was Ben (name changed, obviously). He was the 27-year-old owner of a gaming store. Ben was straight, white and, turns out, attracted to trans women (but loudly confused about it). Letting him buy me a drink turned into a 90-minute therapy session where he inundated me with a brief history of his neuroses about his sexuality. Unfortunately, in the thrall of vodka, I went back to his flat. It continued. A barrage of questions and mini-debates. He – unwittingly – used insulting language, casually derogatory terms – including asking me if I had heard the word “trap” which some friends of his used to describe trans women (‘yeah, I’ve heard that one’). He asked me what I thought of Jordan Peterson, the Toronto professor and author, who has proudly said he would misgender his trans students in defiance of ‘compelled speech’. I slurred ‘Peterson is bullshit’. Not my finest rhetorical performance. “Nah he’s a smart guy,” Ben contended, “plus no-one should be forced by law to use the pronouns someone wants.” Then he leaned into kiss me. I was desperate for validation as a woman and it was bleak.

However, the memory of it all is the best explanation I have for why the world I inhabit feels a little less of a fucking mess with ContraPoints in it. My ‘baby trans’ days of insecurity, taking crumbs of attention from the Bens of the world, are long since over but, still, it’s delightful to know that the trans girls of tomorrow could also tell this type of man to “fuck off and watch ContraPoints” the minute he started his shit. There, on YouTube, she would appear: radiant and razor sharp to give the conflicted young hetero white male all the hits: why Jordan Peterson is actually banal as fuck, why pronouns are actually about functioning in a society not biology, why men who obsess about women not giving them sex become dangerous weirdos online, why its not OK to say ‘trap’ but it is OK to love the woman behind the slur.

Natalie Wynn, aka ContraPoints, is a 30-year-old Youtube content creator, and number two on 2019’s Dazed100. The trouble with the relatively recent emergence of the description ‘YouTuber’ is that its breadth tends to obscure the dexterity of Wynn’s particular craft. In fact, her monthly videos (usually between 20 and 40 minutes in length) are each the product of weeks of work in which Wynn thoroughly researches and writes her script, purchases and designs and builds her own sets, designs and styles her own costumes, does her own wigs and makeup, shoots the entire video in the small hours of the morning (over a week), then edits the entire thing herself, working 16 hour days with the occasional assistance of one close collaborator who assists with script and audio editing. The music for the videos is the only aspect of the creation she outsources. If this were being done in a theatre or even a small cabaret bar, it’s hard to imagine Wynn’s videos being produced by anything less than a team of ten. 

The sheer level of work she is putting in would be remarkable even if her final result were not as astute and hilarious as her videos are. In many cases, her humour makes use of perfectly crafted one liners that capture the self-deprecation and identity angst needed for any viral queer meme (“I look inside myself and ask: ‘Do I feel like a man or a woman?’ And the answer is I feel like shit”). But the true brilliance of Wynn’s work emerges when she pushes the limits of surreal and grotesque: in online trans circles, for example, her name has become virtually synonymous with the word ‘mouthfeel’, which she once used to describe the difference in texture and turgidity between a trans woman’s penis (if she is ‘pre-op’ and on estrogen) in one’s mouth during oral sex from sucking the penis of a cis man (which is typically larger and more rigid thanks to testosterone). In a nod to how much her trans fans have run with her character’s use of ‘mouthfeel’, Wynn went further – roleplaying in a later video as a wine-swilling connoisseur at a French cafe discussing the differences hormones cause to the taste of the penis. In a culture where trans women are usually demeaned and reviled by imagery invoking their genitals at birth, Wynn’s lurid wit runs away with it all so far that the garden variety bigot cannot possibly keep up. Much of the content the far-right has disseminated on YouTube involves a sense of aesthetic, style, humour and community building in its dangerous propagation of racist, misogynist and homophobic messages. Perhaps Wynn’s greatest success has been observing this disparity in how the platform has been harnessed and being part of a loose collection of leftist creators beginning to turn the tide.

Natalie when I came to do this interview I mentioned it on my social channels, and people literally went wild. The thing about being a 30-year-old white transsexual who isn’t ContraPoints right now is that everyone asks me what I think of ContraPoints. For real. Everyone. How do you feel about the concept of fame? I mean I guess people say ‘microfame’ about popular online figures but I think it’s wanky. You’re simply famous.

Natalie Wynn: It’s something that’s new in my life that I haven’t yet formed a fully mature opinion about. If people come to say hi to me on the street they’re very nice about it. I’m not going to be like ‘I’m famous, I hate this!’ Also I’m a YouTuber! I’m sorry, if you put a camera in front of your face and record yourself talking? You have a personality that on some level wants attention. YouTube is a perfect platform for introverted narcissists. That’s a weird thing when I meet fans. When I give this performance on YouTube, there’s a big energy to that. I’m trying to avoid saying ‘big dick energy’.

Yeah it’s a bit 2018. Also we’re two trans women. Literally – cancel the dicks.

Natalie Wynn: Right! So in comparison to that big energy on YouTube, in person I’m very, very small energy. I always feel like a disappointment because anyone who’s seen ‘ContraPoints: revolutionary’ is not going to be impressed with the actual person… Natalie.

Yeah, that makes sense. People refer to you as ‘Contra’. Like, that’s almost an alter ego. Are you quite happy with almost having a separate persona? It’s very Sasha Fierce!

Natalie Wynn: It’s like getting a level of prominence in your field and being known professionally by your LiveJournal name from 2003. It’s just the channel name I picked having not any notion that this was going to be my career. It’s weird. But also one of my colleagues is called Hbomberguy. So, you know, it could be worse.

“It’s just the channel name I picked having not any notion that this was going to be my career. It’s weird. But also one of my colleagues is called Hbomberguy. So, you know, it could be worse” – ContraPoints

You’ve said on Twitter a couple of times about how a lot of the interviews that you have done for mainstream publications that maybe don’t normally look at YouTubers, have focused on your channel’s rebuttal of arguments used to convert young men to the alt-right. It’s certainly a part of your channel but I have to say I think your channel has evolved significantly since that content was central to it? You’ve stressed that you have nearly as many women and LGBTQ+ subscribers and fans, for example.

Natalie Wynn: Well, I think if you looked at the videos I made in 2019 you would never describe this channel as being about deconverting the alt right. In 2016 to 2017 I was talking about that and getting 20,000 or 30,000 views on a video. Now, I’m getting a million views on a video talking mostly about trans stuff. And then suddenly, I’m in the LA Times about how I’m deconverting the alt right. I’m not opposed to it – I’m glad that they cover that aspect, because I’m happy to take recognition of everything that I am proud of. That’s what I was doing. But I wish they had this energy in 2016 and 2017, when it was needed and they were being recruited. It’s only now that people started getting murdered, that the editors that want to publish some stories about it.

I think there is some crossover between your audiences – if you like – the young male audience and then the women and queers. For example, one of my trans friends said – about you – “my boyfriend that has watched all of her videos, and it’s spared me hours of conversation”. I think it’s useful that you’re afforded that gravitas conferred by the male sphere because now you’re getting some of the male audience to look at the trans content.

Natalie Wynn: I’m happy to talk to men. I think I’m good at it. I think.

Well you have insider knowledge, Natalie! See if I were a cis journalist I couldn’t make that joke.

Natalie Wynn: I mean but also… yes. I can imagine that social perspective better, perhaps. But I also feel like I’m somewhat losing my grip on that as well. But for now I want to try to use it in the best possible way. People will sometimes criticise me for doing things in a way that will be appealing for the people who need to listen to it. I did this video called “Are Traps Gay?” which has a million views and I was heavily criticised for making it initially.

Yes well that’s the one my trans friend meant. That’s the one the boyfriends and other miscellaneous trade watch. The trans women who date cis men are all sleeping with guys who’ve watched that video, Natalie. I speak from experience.

Natalie Wynn: Well, you’re welcome trans women! But seriously I hope that that would be the effect of something like that – a piece of big discourse that could actually make lives easier. You know a few people have accused me of making a dating ad for myself with that video. Which – yes – guilty. But also I would like to think it helps others.

“I didn’t discuss anything about myself in that video so bad that cis people aren’t assuming worse about me anyway. That’s kind of how I see it. I think that trans people are already regarded as perverse and degenerate. It’s only uphill to go from there” – ContraPoints

I’ve always been genuinely surprised by how much you put yourself out there, in terms of the levels of personal information you share in your videos. The first video of yours I ever watched was your video on ‘autogynephilia’. This pseudoscientific theory that some trans women are actually men with an all-consuming sexual fetish to roleplay as women. In reality, it’s a theory now mostly used to slut shame individual trans women online. Your video did this thorough rebuttal that deeply impressed me but, you know, it included a lot of personal sexual disclosure from your own life.

Natalie Wynn: When I think back on a video, I’m not sure if I made a mistake. The idea, when making that video, that it was going to hit a million views was inconceivable. But you know, the popularity of it also forces the question: why is it so popular? It’s clear that some people are Googling. Now you could ask me ‘why would you be so sexual with it?’ Well, here’s the thing: as a public trans person I didn’t discuss anything about myself in that video so bad that cis people aren’t assuming worse about me anyway. That’s kind of how I see it. I think that trans people are already regarded as perverse and degenerate. It’s only uphill to go from there.

I’ve had my fair share of transphobic abuse online, and I get some of what that’s like. I think now it’s safe to say it doesn’t compare in scale to what you’re dealing with. However, I always notice you are very transparent about personal things relating to your own transition. Like how it’s important to you to pass in daily life. I always worry about putting that out there now because one gives people ammo. If you say ‘I want to pass’, the first thing a troll will do is say ‘sorry bro you have clearly tried hard but don’t pass’. They hone in on that anxiety to hurt you. Are you concerned about that at all?

Natalie Wynn: What is the point of coming out, if I don’t then tell people who I am? There’s nothing so horrible I can put out there about myself that bigots wont have said about me to begin with. I don’t really know if I’m even capable of bringing any more of it on myself at this stage. The people who want to hurt us know how to hurt us. They know that we care about passing! They know that. I’m not really convinced that not mentioning or not saying you care helps. They know you can upset most trans women by saying ‘you have really mannish clockable hands’.

Yeah hands are the final thing they go to when the person has ticked every other feminine box.

Natalie Wynn: Yes, hands are the last refuge of the transphobe.


Do you still read online comments about yourself?

Natalie Wynn: Oh god yes. I’ve got better – I don’t go to the places where I’ll only encounter hate. My days of reading about myself on 4Chan are over. But I read my own comments section and look at what people are saying on Twitter. I’m too much of a junkie for the feedback – I want the positive comments too.

I think there’s definitely a boredom that comes from talking about transition once you’re several years post transition. I wondered if you feel that (given we’re the same age and similarish stage regarding our transitions)? When you’re initially going through it it’s the most interesting thing at hand, obviously, but I find discussing it boring now and that’s a recent change for me. And I remember older trans women suggesting I might feel that way and I’m starting to get where they were coming from.

Natalie Wynn: I have no doubt that in a year or two, I will look back on this entire period, and just cringe horribly. It’s as much a curse as it was a blessing, having the platform I have, in the sense that is thoroughly documents my pre-transition self. That videos of me pre-transition are freely available online is honestly one of the biggest sources of gender stress in my life. But I think that when you’re going through the first two years of oestrogen transition it’s so incredibly difficult, it’s painful. It’s so insecure and it really challenges your understanding of the world and gender and just so many things. It does feel like the most interesting thing in the world. Absolutely. I’m sure that to older trans women, it is completely exhausting and obvious. And I’m sure that I will find it completely exhausting and obvious in a couple years myself. But, you know, baby trans are always gonna baby trans!

“My days of reading about myself on 4Chan are over. But I read my own comments section and look at what people are saying on Twitter. I’m too much of a junkie for the feedback – I want the positive comments too” – ContraPoints

Presumably you have to negotiate your own privilege now too? In that you can’t quite speak to the majority trans experience because you’ve made a decent amount of money from your Patreon which has allowed you to access surgery and other things that put your experience outside of 90 per cent of trans people’s daily lives and struggle?

Natalie Wynn: Yes there’s now an aspect of – how can I put this – envy management I have to do online. There’s this bizarre irony that happens where, for talking about the trans experience on the internet, the internet gave me money. And now the internet is intensely resentful that I have money. I get why. I would be resentful too. I have things that many people want and can’t get. And it’s not fair. I find myself being very cautious not to say things that are going to make me sound really cluelessly out of touch – which, honestly, I guess is increasingly a risk.

Public-facing trans women often go through a cycle with fellow trans people where they’re put on pedestals and then they are seen to have fucked up and torn down, sometimes viciously. It’s horrible for the trans woman involved often because she’s being held to account for a systemic issue of there not being enough trans people to avoid overinvesting in a few figureheads.

Natalie Wynn: Yeah I agree. I was thought to be a funny and humorous person early in my transition and people basically pinned on me the job of representing them – which no one person can possibly do.

I remember reading in another interview with you that the reason some of your videos parody or use the format of a TV debate where you play every role is because that format is set up to make trans women, in particular, fail? Is this because if we are too aggressive we get told we’re mannish but if we’re too reserved and feminine we lose the debate?

Natalie Wynn: 100 per cent. I think that a trans woman is inherently at a massive disadvantage in a debate format. I mean if you tried to debate someone like Ray Blanchard (the sexologist who created the pseydo-scientific concept of autogynephilia) the minute you get there there is this is look on his face, like, ‘Oh, great. The adults have to stop talking now. Seriously. Because we have to deal with this delusional child’. The audience is going to sympathise with that, because they don’t understand trans people! They understand ‘rational’ white male scientists. So what you have to do is exactly what you just said: you have to either be very meek and feminine – in which case, the perception of your femininity is viewed as a losing point in the debate because debate is a kind of inherently macho activity. But if you come in macho then they see a crazy man. So there’s really no winning.

You recently did an excellent video called “Gender Critical” which was about trans exclusionary feminism or trans hostile feminism or transphobic feminism. However you may describe it. But for clarity they tend to style themselves as ‘gender critical’ and their opponents - trans people and their cis allies - commonly refer to them by the acronym ‘TERF’.

Natalie Wynn: Yeah.

Now you are probably well aware that the type of anti-trans feminism you discuss in that video has much much more influence over mainstream feminist discourse in the UK than the platformed liberal and leftist feminism in America. But given that you did such a great video, I wonder how you think this huge conflict is going to end? It is very based in the online sphere and offline its easier to have constructive conversations but now at its core it is so vitriolic; there is no good faith, there’s no grounds for conflict resolution. Do you think it can be resolved?

Natalie Wynn: Well, the way I see TERFs losing, and I know I’m not the first to observe this, but they can’t really build alliances very effectively. I think that in progressive spaces, trans people will find sympathy. I do believe that. And then TERFs get kicked out. That seems to be what’s happening. In a lot of progressive spaces TERFs just get kicked out, because they’re bigots. So what TERFs end up doing instead is they build alliances with conservatives, in which case, they kind of have to drop the feminist causes and just become conservatives. So TERFs have kind of isolated themselves, where they can’t be allies of other progressives. So what they’ll do is just become conservatives – if they’re that committed to hating trans women, that they are willing to drop feminism entirely, basically, then they’ll do it. And I think they have started doing that.

Your recent video “Trans Trenders” I watched a couple of days ago. You said it might be your last video on trans identity beforehand on Twitter. That video ended on a note of ‘why do we have to explain our identities?’ Is this about you feeling burnout, or a personal decision to walk away from ‘identity’ as a subject for your content?

Natalie Wynn: I’ve spent a lot of time trying to justify myself to the world in a rational, philosophical way – me, my identity and my existence. But I’ve got to the point where there’s things I can say that are pretty convincing in my case. But the problem with trying to come up with a theory that explains why trans people are valid is that any theory like that will inevitably exclude some people. And that will be upsetting to those people who are excluded. I personally cannot think of a theory that includes everyone. So I’m kind of just done trying. And I think that having a good theory is not ultimately what causes people to accept us anyway.