For the last four years, Natalie Wynn has created videos that tear down fascist arguments and right-wing talking points. With over 1 million followers on YouTube, where she goes by the name ContraPoints, Wynn employs darkly ornate costumes and surreal decadence to discuss social justice in incisive video essays that frequently approach feature-length. Whether she’s sipping Champagne in a bathtub or dressed as a catgirl, the former philosophy PhD candidate takes a scalpel to whatever subject she’s on, from incels to the concept of “cringe.” Though she can appear aloof while in character, the real Natalie Wynn is an open book. During our call she talked sours, Schubert, and the unique pain that often comes with being a trans woman online.
Tell me about your experience with beer.
Oh boy. Well, I guess I don’t drink as much of it as I used to. I guess I started drinking when I was a teenager. I guess a lot of my 20s I was, like, always on the threshold of alcoholism, so that’s… you know. Like, it’s a complicating factor in terms of talking about it as a gustatory pleasure. But I do—I always enjoy it, and I still do. I guess these days, I really like sours and witbiers. And I don’t really like IPAs. That’s kind of an area that takes me—I feel like that where I’m alienated from beer people, is that. I want to drink, like, half of an IPA because that’s about the right amount of pine mixed with perfume. I feel like when I’m drinking beer it’s because I want to get like buzzy, but also in a way that’s hydrating. Because if I just want to get trashed, I’ll just do shots, or I’ll just drink sparkling wine. But beer is like, “I want delicious water that makes me feel better about myself and about the world.”
It doesn’t dry you out like vodka does.
That’s what I mean, yeah. But IPAs do make me feel like that. It’s like the liquid equivalent of smoked meat.
It’s like drinking a Christmas tree.
Yes, it’s like drinking a Christmas tree, which there is an occasion for, granted.
You’re in Maryland, you said? So, you have good seafood. Sours really pair well with seafood.
Exactly. So, my favorite is Dogfish Head SeaQuench Ale. It kind of tastes like my ideal beer. It tastes like you poured yourself a nice cold glass of ocean water and squeezed a lime into it. It’s perfect. Because I love the ocean. I love citrus. I don’t know. And then, yeah, you actually drink it with oysters—it’s amazing.
Did your relationship with beer change when you came out?
Yeah. It did. I stopped feeling like I had to pretend to like IPAs. That’s a big one.
[IPAS are] like the liquid equivalent of smoked meat.”
I hear trans women say that if they’re at a bar, they want to be holding the most feminine glass. In just an affirming kind of a way, like, “OK, I have to have a martini now. I can’t drink this massive beer.”
Counterpoint: a massive beer makes your hands look small and delicate by comparison.
Oh my god, it’s totally true.
You shoot your videos at your home, so has much changed in quarantine?
It’s very uncouth for me, I feel, to complain about quarantine, because I have it so much better than so many other people. I have not taken a financial hit as a result of this. I am able to work from home. I am comfortable here. So many people are in so many horrible situations that I feel like me complaining about my petty bullshit is, like, gauche.
But nonetheless, let me complain: It’s actually been very emotionally hard on me in quarantine. A lot of my friends live in other cities, and so I have kind of gotten used to traveling every once in a while and going to visit them. Can’t do that now. I kind of began this year with a breakup and a bunch of weird sexuality trauma. I ended a relationship. I kind of lost my best friend. I came out as gay, and then, coronavirus hits, like, a month after all that. And so, it’s like, “Well, great. I’m now like trapped inside to just sink into myself and reflect on what I have done and the ways I’ve deluded myself, and it’s just not good.” It’s not what I needed right now. What I really needed this year to be is a time to go out and have fun and meet new people and find myself, and instead what I have is confinement in a cell of torturous reflection. It’s terrible. But what’s pulled me out of it was I’ve actually moved to a new house, and so I have this interior decorating-fueled mania that’s propelling me forward at the moment.
Are you shopping online for furniture?
I’m shopping online for furniture, which people say not to do, but actually, it’s worked out pretty well for me. I got my measuring tape out and my little plans. I guess the big thing I got, and I did go in person to look at this. I just bought a grand piano, so that’s like the biggest purchase I’ve made in my life, because I’m not a car person, so I’m not going to spend money on that. But my Lexus is this grand piano. I went to play it in person, and I fell in love with it, and I play it like three hours a day.
What kind of music do you play?
I play classical music. My first two years after high school,I was a piano major at Berklee College of Music in Boston. That’s kind of a contemporary music school, so I was doing, like, jazz piano. But now I just sit around playing Bach and Schubert. That’s what I like. And that’s honestly kind of saved me, I think, the last month or two. I mean it’s not a replacement for a love life, but it sort of is. That’s what it’s been to me.
How do you mean?
I feel like music is kind of—it has some kind of emotional affinity with romance. Especially Schubert, which I love to play. It’s like the expression of this unfulfilled longing. This music written by this little blind incel in the early 19th century. And I don’t know, I just feel like Schubert gets me. Like he just gets what it’s about to be a human. And it just makes you feel less alone, because you’re connected to it. I don’t write my own music. I play other people’s music. I feel like I’m with Schubert. It’s very romantic.
Do you listen to contemporary stuff?
I guess I used to. I’ve been on a real vintage kick lately, but last year I got very into like PC Music and hyperpop, Sophie and all of that kind of music. That was kind of my soundtrack last year, and now, this year, I’m listening to Billie Holiday. And lying in bed and crying.
I noticed that you’ve taken down some of your old videos recently. Why?
I just find it intolerable to have them on my channel still. I mean my relationship to my transition, my past, is pretty ugly, honestly. There’s almost no way to talk about this without getting super heavy. Is it OK if I get super heavy?
Yeah, of course.
I guess in some ways, my life is very, very privileged and very easy, and I’ve succeeded beyond my wildest dreams, et cetera, et cetera. And in other ways, I feel like I’m just sinking deeper into this shame that just consumes me. And I can’t stand watching my own videos. Like, not even like ones from last year, because I’m sort of disgusted by myself. And I can’t stand how I look. I can’t stand how I sound. You know, I’m just embarrassed. I’m embarrassed about who I am, in a sense.
Do you think that might be you being more critical of yourself than other people would be?
Well, I’m sure I’m more critical of myself than most people are. But also, I don’t know. There’s also a lot of transphobia in the world, and a lot of it finds its way to my eyeballs online. And I don’t know, I think a lot of that stuff has really kind of sunk into me and kind of fucked me up, to be honest.
This is where we can talk about J.K. Rowling. You go on Twitter, and it’s like, “Oh, fuck. She’s trending again. What the fuck did she say now?” What’s your take on her?
As far as J.K. Rowling is concerned, I think she’s pretty typical of what’s called a TERF. Transphobic radical feminism has been a thing for decades, and it seems to be motivated by fear. Fear of men, right? I think that’s underneath all of her writing on this, right? There’s this fear that men are going to dress as a woman to appear non-threatening and then unleash their terrifying male domination when it’s unexpected. Which is I think—I think it’s kind of a thread that’s in Silence of the Lambs. I have not yet read her [latest] novel. It’s 900 pages, the Infinite Jest of TERFery.
I had no idea it was 900 pages.
I think it’s 900 pages. Fact-check that. I will see how much of it I can get through. But the fear of men seems to produce a strong need to be able to differentiate very definitively and finally and clearly between men and women. Women are safe and OK. Men are dangerous and scary. And if the two categories start bleeding into each other, it attacks your sense of safety if you think like J.K. Rowling does, right? And so, I think that’s sort of where this comes from. And then it sort of branches out into all these, like, meta debates and all this stuff about cancelling and Cancel Culture and free speech—all these kind of secondary issues that they talk about as a result of the clash between trans people and transphobes.
The measure of fame that I have is kind of like micro fame, relative to a certain kind of community of people. It’s awful. It’s horrible. I wouldn’t wish fame on my worst enemy.”
You did a video on Cancel Culture. And well, I mean this is going to be heavy again, but you’ve been on the receiving end of that. How did you get through that?
It was awful. I mean the last 12 months of my life—it’s hard for me to explain this to other people in a way that I don’t sound crazy—but it’s been like one of the worst years of my whole life. Despite the fact that I’ve been financially very successful. Being cancelled, it had no negative financial impact on me at all. It may have had a positive impact in that people felt sorry for me and donated. But the emotional impact is huge, and the social impact is huge. Money’s not the only thing that matters, as it turns out! Five years ago, I was an Uber driver and struggling to pay rent. It really seemed hard for me to believe that money didn’t buy happiness, because you know, so many of my problems came from this fundamental anxiety about how am I going to pay for things, right? And it’s true that having money now, that anxiety is dealt with, but all the other things in your life don’t get fixed by this. And you know, the measure of fame that I have is kind of like micro fame, relative to a certain kind of community of people. It’s awful. It’s horrible. I wouldn't wish fame on my worst enemy.
You know, it’s been hard, because I feel kind of also sort of at this point like very cut off from the trans community, because I’ve sort of become this hated figure for what from my perspective is a total misunderstanding of things that I’ve said and which seems to stem from I don’t know what exactly. I don't know why I’m as hated as I am, but it’s almost like a cornerstone of what it means to be a radical young queer person on the internet is to hate ContraPoints. And it makes me sad, and it makes me lonely. I don’t know. I don’t know what to do about it.
I think part of it is that like Twitter is just not a great place for nuance and a long discussion, right?
Yeah, and I mean if you’re talking about the most infamous tweet I did, the “being asked your pronouns tweet” where I was trying to express that I get uncomfortable when people—especially if it’s mostly cis people in a group—if I’m asked what my pronouns are. But that got interpreted as, “Oh, don’t ask people their pronouns ever, because fuck you, trans people” or something like that. And obviously, I did not express myself perfectly, because that’s how Twitter works for me. It’s emotional. It’s reactive. It’s not very well thought-out.
It’s when you’ve had several drinks.
Yeah, exactly. You have a feeling, a moment of frustration, and you just want to express this feeling that you’re having and not necessarily think through every possible interpretation and how it could be misread, right? But that is kind of what happened. It was the end of a sequence of a long sequence of things that people were irritated with me for. Then, the final nail in the coffin was me having Buck Angel as a voice actor in one of my videos. And I think it’s a complicated situation, because on the one hand, like, there’s the radical trans people who think that I’m transphobic. To some extent like they’re onto something that’s real. Like we were just talking about me deleting my old videos and me having this awful relationship of shame to my transition, to my own videos and stuff. Like, yeah, obviously I do have a lot of internalized shit going on, and it probably does manifest in certain ways that they’re picking up on, right? So, I don’t want to totally invalidate what they’re saying about me, because I do think that they’re sort of clocking something that’s there. But I also do feel somewhat that I’m being treated unfairly if the response to it is just, like, total exile. Because I’m still a human being, and I still am a trans person, and I still want to do better.
And you’re still doing what you do. And your videos are becoming feature-length. The last one was the length of a Marvel movie.
Yeah, it’s actually getting a little out of control. I’m trying to do shorter videos, because I think it’s getting unwieldy.
Do you think that’s because you can’t do anything else at this point? Is that why they’re becoming so long?
Well, I think a few things. One is like there’s a kind of pressure that you feel to kind of constantly be stepping it up and escalating all kinds of things from the length to the production value to the costume budget. The other is that as I get more experienced doing this I’m more able to produce a longer train of thought than I was when I was doing ten-minute videos to begin with. And I actually don’t like the way it’s trending. I don’t want to do two-hour videos. It’s too long. It’s too long for a YouTube video, so I’m going to try to cut back down to 30 or 40 minutes, which I think is kind of a good length.
Going back to how cancelling has not affected you financially, this is kind of the frustration with someone like Rowling—it’s not going to affect her one bit. Like you said, you got more people donating.
It’s like advertising practically. Traumatic advertising but advertising.
So how do we deal with someone who’s that big of a deal and change their minds? You’ve changed minds. Your incel video, specifically.
I mean the only way I know that I personally am good at is through my videos. People will often ask me, “Oh, how do I convince my Mormon parents to accept that I’m a lesbian?” or whatever. And I’m like, “I don’t know.” I don’t do that kind of persuasion. I don't argue with my extended family. I’m not good at that. What I’m good at is producing media that, to anyone who has the attention span to watch is, I think, likely to make them more sympathetic to me by the end of it. I did this video about Jordan Peterson more than a couple years ago now, who at the time was like the figurehead of anti-trans panic, basically saying, “Oh, we’re about to lose all of our free speech rights, because these authoritarian pronoun laws have been passed in Canada, and now, free speech is over.” People would make this argument all the time to me. “Well, why are you trying to put people in jail for misgendering you?” It’s never happened, by the way. No one has ever gone to jail in Canada for misgendering someone. So, it’s complete nonsense and panic. So I did make a video about Jordan Peterson specifically designed to pull in some of his fans. Most of his fans, they were kind of like 21-year-old men or boys really, and their whole argument was sort of based on, like, “Oh, we’re the edgy free speech brigade standing up against this PC bullshit.” So how do you bring it up to someone like that? Well, you out-edge their father figure, right? So I made a very edgy video where I take a bath with Jordan Peterson and pour milk on his face and talk about doing PCP.
And call him “Daddy.”
Call him “Daddy,” yeah, and talk about this whole pronoun argument and this sort of panic about—Jordan Peterson’s phrase was “postmodern neo-Marxism,” which is a phrase I find to be just total nonsense. I feel that video was pretty effective, and I think that a video like that about J.K. Rowling isn’t a bad idea.
No, it’s definitely not a bad idea. So who are you voting for?
Joe Biden. Am I excited to vote for Joe Biden? Fuck no, but I mean I think Trump must go by whatever means available. I do think Trump is more or less an aspiring autocratic dictator who does not believe in democracy, does not care about democracy, is not interested in elections, is only interested in his own personal power. And I think it’s incredibly dangerous not just to trans people or marginalized people but to this democracy as a whole. And I think that no, voting for Joe Biden will not solve the problem, many of the problems in this country. Not at all. Not even close. And I fully expect to protest a Biden administration, particularly on issues like police brutality, where Biden’s given very little sign that he’s going to change anything. However, I think that having him in the White House over Trump still is something worth working for. It gets the tyrant out. I don’t see any way that you could say that it’s not better to have a president who’s not actively telling white nationalists or white supremacists and militias to stand by. And as for the issues where we don’t expect Biden to do anything—police brutality and so on—I think a Biden administration is more likely to be pressured by protests, by unrest than a Trump administration, which is only going to use it as a pretense for law and order, screeching and increased military police presence.
How can you ever think that you’re trans, looking at the way that trans people are portrayed as a punchline or as monsters?”
What’s really I think the thing that’s most disturbing to me is that we see that 40 percent of the country is totally fine with authoritarianism. Like, it’s fine as long as it’s their kind of fascism.
I fully believe that 30 percent, maybe even 40 percent of the country, that there’s just no limit or no bottom to how low that they’ll sink in following this man. I mean, Trump said it himself, “I could kill a man in the middle of 5th Avenue and not lose one voter.” I believe that. I believe him when he says that. And there was a time when I thought “Oh, people will surely come around.” Like they’ll see that this is a fraud, that this is a tyrant. Well, I don’t think so. I think that people, that a lot of Trump’s base, they don’t care about democracy. They care about winning. Winning big and following this monster wherever he goes.
One would hope that seeing someone you know and loved being attacked by all this would help.
Oh, I agree. I do think that it helps kind of anchor people to a sense that they’re dealing with real human beings. I mean, knowing someone who is gay is a major factor that contributed to acceptance of gay people. I think that with trans people it’s tricky, because there are fewer of us. It’s not very common. So, most people don’t know a trans person. It’s sort of easier to attack us since we’re fewer. A smaller percentage of the population has any kind of human connection to us as a group at all, and that’s tricky.
But I think that it is one thing that YouTube is a spectacular resource for—because while there’s a lot of criticism of the way that the relationship between a creator on YouTube and their audience—the piece of jargon is parasocial. The idea is that you form these pseudorelationships with your own audience where when you become fans of a YouTuber, you feel like you know them. You feel like you’re friends. OK, that has an insidious side, because it can become pretty unhealthy to have lived in a sort of delusional role where you feel like you’re friends with a person. You feel like this person owes you things when they don’t know you. But that’s especially relevant. It’s kind of one of the things that’s going on with the cancelling of stuff that I’ve talked about with our experience where the audience, if I do something they disagree with, it’s like, “Wow, this person I thought was my friend is now betraying me by doing this thing.” So, that’s obviously bad.
But the good side is that if you’re a trans YouTuber, people who are fans of your content, who like your content, it sort of functions as you are their trans friend, which has this humanizing effect. And now, when they see political attacks on trans people, they think of you, and that I think is hugely powerful. I mean, YouTube was a hugely powerful thing for me and coming to understand myself as trans. Because we grow up in this media climate where, like, how can you ever think that you’re trans, looking at the way that trans people are portrayed as a punchline or as monsters? Well, a huge thing for me was seeing real trans people on YouTube transition, and suddenly, it became this thing. It was like, “Oh, I can relate to this. I can relate to these people. I can see myself in these people. And now, I can understand myself as trans.” Whereas, I couldn't see myself in these awful caricatures.
And people think “Oh, they’re all like this,” right? So it creates pressure on every trans person to be a better example.
It’s a horrible thing. When you have a million people watching you like I do, the pressure is incredibly unfair. I should be able to be a human, and I should be able to fuck up and be an asshole sometimes, and just be a human being. But I feel like I can’t do that because of the immense pressure on me there is to represent an entire community. The community is far more diverse than me as a person. And this pressure is not just on me. It’s every trans person. That we all kind of feel to be constantly representative. It really plays a role I think in turning trans people against each other and creating awful feuds that seem to sort of plague this community and the resentment and the envy and the scorn. I think it originates from this collective trauma basically of rejection and the unfair pressure to constantly be not just yourself, but the mascot of a whole population.