“The first time I used milk in a video was because I thought it looked like semen, and I thought that was funny,” says Natalie Wynn, otherwise known as the American YouTuber, ContraPoints. She's chuckling down the phone as she dispels this Reddit myth that she uses milk in her videos to reclaim it from the alt-right, which has taken to wielding it as a symbol of white supremacy. “There’s a complex semiotics of milk,” she admits, "but why did I pour milk on my face? Was I thinking about its connection to power or sex? I don’t know, I probably just laughed!


These sorts of elaborate theories aren’t uncommon when it comes to Wynn's work, and they’re evidence of the intense attention people pay to her videos. Combining humour, drag and philosophy, she is one of the most incisive and compelling video essayists on YouTube. Her latest video 'Gender Critical' (a term radical feminists have taken to using in reaction to being called TERFs) racked up almost half a million views in a day. From the context of comedy to transphobic memes, ContraPoints is doing the seemingly impossible: making nuanced and controversial political debates both sexy and engaging.

Wynn “tinkered” on YouTube for more than a decade before arriving at this formula. To begin with, she was “a minor participant in YouTube atheism content, because that’s what you did as a person with opinions in 2008.” But in 2016, she began ContraPoints: a response to the atmosphere she saw building online. “I noticed a surge of political content around GamerGate in 2014, and it was pretty right-wing – or at least anti-progressive,” she tells me, citing a spectrum of content ranging from the centrist to the straight-up Neo-Nazi. She decided to create her own videos, and these “tinker-toy attempts” at deconstructing social justice issues through a left-wing lens soon caught on. More importantly, they became a creative outlet.

Until that point Wynn, who is now 30-years-old, had devoted much of her life to academia. She was born and raised in Virginia but later moved to Illinois, where she studied for a PhD in Philosophy at Northwestern University. “The idea of being an academic for the rest of my life became boring to the point of existential despair,” she recalls half-jokingly – it’s hard to tell: she later describes her PhD as a “guided tour of history’s most boring homosexuals.”


She describes being fundamentally miserable, juggling numerous jobs to “fund failed artistic attempts.” That’s when she noticed that pseudo-intellectualism was beginning to creep into right-wing discourse, propelled largely by the likes of “phoney philosophers like Stefan Molyneux”, whose popularity proved there was an audience for philosophical takes on political issues. “They were selling it to people who craved this kind of commentary, but were just getting into a horrible version of it,” she says. ContraPoints was conceived to balance the political playing field by dissecting issues through a left-wing lens. “That’s one thing I learned in my philosophy training,” she adds, “if you’re writing a paper on Aristotle, you have to first show that you understand him. Then you can make your counter-argument.”

Race was a key focus of ContraPoints’ earliest videos. In pursuit of a relationship, Wynn moved to Baltimore after dropping out of University. There she found a city in the midst of “an uprising” after the murder of Freddie Gray – a young, wrongfully-arrested black man who died due to injury in police custody. No officers were charged. Soon she started seeing “violently, viciously racist” online comments which were being ignored, a fact which frustrated her. “I thought that if people are leaving these comments, they're thinking these thoughts all the time," she says. "People told me I was crazy, but then the 2016 US election confirmed to me that people were voting the same way they were leaving YouTube comments.”

Online radicalisation became another key theme in ContraPoints videos. Her essays on ‘decrypting the alt-right’ and incels garnered millions of views, as did her thorough debunking of prominent alt-right commentators like Ben Shapiro and Jordan Peterson.


“They take these tired, old-fashioned racist reactions and present them as an edgy new thing, and it’s powerful rhetoric,” she says. “They understand how to make these ideas sexy and dress them up for public consumption; what drives me crazy is that the left doesn’t seem to have that intuition on how to publicly present a thought.” The fatal impact of this alt-right rhetoric was laid bare by the recent Christchurch mosque massacres. “People still think these are just memes, just jokes,” she says, her voice heavy with frustration. In a tweet posted in the wake of the tragedy she wrote: “No satisfaction now, just anger. No one listened.”

Wynn acknowledges that to de-radicalise someone you have to engage with their ideas, but this method isn’t exactly popular. “The only way I was able to make these videos was to have conversations with centrists, or with people that were going in an alt-right direction,” she explains, “I was doing what you’re literally not supposed to do, which is to talk to them.”

This approach is rooted in the understanding that ‘politics is aesthetics’ – in other words, the way you make an argument is as important as the argument itself. “It’s not just about calling someone out and using logic,” she explains, “because there are emotional and psychological reasons that people hold their political convictions. From a psychological standpoint, you have to empathetically enter a person’s world; not just why do they think what they think, but why do they feel what they feel? Repeat that back to them and you can really gain traction.”

As a persuasion strategy this can be effective, but she describes receiving “credible kickback” from the left in the past “for having any interaction with somebody who is publicly right-wing.” Now she makes a deliberate effort not to publicly have interpersonal contact with them – “I observe them secretly and then report on them in this very controlled video form.”

Some topics are more personal than others. Wynn transitioned as her YouTube career was burgeoning, and she dives deep into subjects like 'gender critical feminism’ (now synonymous with ‘transphobia’) which require huge amounts of emotional labour to unpack. “I didn’t understand how difficult it would be to transition in the public eye and look back at pre-transition videos – it’s sort of humiliating and painful,” she explains. “I’m eventually going to have to be at peace with it, but I’m not right now.”


On this note, the rising popularity of the ContraPoints channel doesn't come free of anxiety. It’s hard not to politicise the autonomy she has over her content and her image in a world which often views trans communities through a voyeuristic lens. “I get to decide how much makeup I’m wearing and in what lighting, which is important because there’s this incredibly complicated politics around the physical appearance of trans people,” she explains. Understandably, Wynn is acutely aware that allowing media outlets in requires not only a sacrifice of control, but also a huge amount of trust.

She also describes transition as “the final nail in the coffin” of her hopes of becoming a public debater. “To be good at it you have to be confident, assertive, almost a little aggressive. In a trans woman those qualities will always be read as masculine, so in order to win the debate, you have to lose the debate.”

Comments like these feel out of step with her sharp, sexed-up and seemingly fearless online persona. “It’s complicated,” she says of the expectation we put on YouTube celebrities (although she laughs when I imply she fits the bill) to allow us unfiltered access to their lives. “I would say I’m a little impersonal – my main persona is an idealised version of myself," she says. "It’s how I wish I argued in person! I’m actually very timid and non-confrontational.”

That’s not to say she aims to be aspirational. “You have to put some of the darkness, shame and self-disgust in there – it’s about having enough of myself in the mix that I feel like I’m being authentic.”

Screenshot from 'The Aesthetic'

YouTube thrives on the illusion of genuine connection with creators we love. “It allows you to feel that you know this person on the screen, and that’s important for trans people in particular because there just aren’t many of us. As a prominent trans person, you hope that someone feels they know you and then thinks of you at the polls; you hope to impact the way they act when they encounter a trans person in real life.” But with this lack of visibility comes pressure to perfectly represent an entire community. “A lot of trans people place hope in me as a sort of public champion,” she says, “so if I disappoint them it’s like this slap in the face. I’ve been accused of transphobia in the past; people think I could betray them at any moment.”

She describes one particular backlash around ‘The Aesthetic' – a dialogue video (in which Wynn plays both characters) between Justine, a hyper-feminine trans woman, and Tabby, the “militant radical”. Wynn wanted to “explore ideas without necessarily endorsing them,” but she received backlash for not making her opinions on assimilation and aesthetics clear. “People didn’t like the ambiguity," she says, "so in the absence of me giving my opinion, they felt they had the right to speculate and assume the worst.”

Ironically, the video – which Wynn reiterates that she’s proud of – actually serves as meta-commentary on the pressures placed on trans women, which are heightened for public-facing trans women. “I’m definitely not claiming any kind of oppression. I want to make it clear that I’m the lucky one,” she says. “But I don’t think people get the intense scrutiny I get from all sides. I do feel like a lot of the criticism I got for that video was unfair.”

Wynn doesn’t claim to speak for an entire community; her views are inevitably shaped by her experience, and as her profile grows she acknowledges that hers will become “less relatable” to a large swathe of people. “Still, I’m not the only trying to change negative representation of trans people – there are lots of trans creators out there,” she says.