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In the non-linear universe of the extremely online, a new video by Natalie Wynn, aka ContraPoints, still retains the power of an event. Wynn is a former adjunct professor of philosophy who, after stints as a legal assistant, Uber driver, copywriter, and would-be novelist, found a dedicated audience of millions seeking political instruction — or at least honesty and a little bit of glam — on topics from “Pronouns” to “Degeneracy,” “Decrypting the Alt Right,” “Opulence,” “Violence,” and “Cringe.”

Wynn’s YouTube videos are scripted dramatizations of diligently researched essays, performed by a cast of alter egos with an array of diagrams, quotes, and props, like guests at a murder mystery weekend devoted to the discourse. By framing her videos as dialogues, she has constructed one of the broadest Overton windows to achieve mainstream success. In an age of ever-tightening information silos, simply voicing both sides of any argument is as equally subversive as donning two-inch silver nails to talk about fascism.

Wynn had already accrued a significant fan base when she transitioned in 2017, and she has applied the same open, discursive approach to “autogynephilia,” “TERFs,” “transtrenders,” and other aspects of trans life that do not often see the light of day without adrenalin and keyboard smashing. It also enables a unique perspective. “Let’s talk about bone structure,” she says in a video about the incel phenomena and its phrenological fetish for the square-jawed chad. “As a trans woman, I know what it’s like to obsess over millimeters of bone.”

As the snow fell in waves over Baltimore and Berlin, we subjected Wynn to our in-house pop cultural test, asking for flash responses to a series of prompts that took us on a journey from NASCAR to anti-vaxxers, the space race, centrists, and “witchcraft for rich people.”


“I ended up here by accident. I moved after grad school for a relationship which ended shortly after and just decided to stay because the rent was cheap and I had no money. I’ve thought many times about moving to LA or New York or some fashionable place, but for some reason I just can’t bring myself to do it. There are no places anymore — only Zoom.”


“Before Covid, I would’ve said they’re a diverse group of people who come to it for different reasons. There’s Black Americans who are anti-vaxxers because they’re historically suspicious of a medical establishment that has experimented on them without consent. Then there are the upper middle class, white people in Hollywood, led by women, who just kind of feel like they’d rather do something with ginger and honey. Needles seem to trigger a lot of fears. I think a lot of neurosis is based on the body’s boundaries. So usually that’s sex, food, and, I guess, needles.”

Culture Wars

“I think there can be a material basis to a culture war, or at least a geographic one. If you look at the United States, anyway, we’re aware that a political map looks mostly red because most of the empty places in this country are red and most of the high-population places are blue. I think a lot of this has its roots in old debates. One is about federalism versus anti-federalism. Is this one nation, or is it a loose confederation of separate states? There are long-standing resentments between people in the western part of the country, for example, who feel that they’re being ruled by the urban capitals in the east. This history involves things like moonshine being illegal — which is where NASCAR comes from. That’s just kind of oppressive. It shouldn’t have been illegal — I guess this is my pro-NASCAR take. I think this intensity of resentment has motivated a lot of Trumpism in rural areas. It’s not that they think Trump is one of them — of course, they know he isn’t. They like that he pisses off the smug assholes on CNN and the liberal fake news media and the Obama supporters. He’s the enemy of their enemy.”


“As the Internet becomes the main source of political information and discussion, one trend I’ve noticed is that everyone hates centrists. The conservatives hate centrists, the leftists hate centrists, communists hate centrists, fascists hate centrists, all four corners of the political compass have their daggers pointed at that center, which has partly to do with the hipster tendency to despise the mainstream and conceptualize your own identity in contrast to the normies. I know a lot of people on the left have this incredibly supercilious attitude towards centrists and ‘the Libs’ because they’re not radical enough. Most people have not been red pilled, blue pilled, Marx pilled. Whatever pill they’re supposed to have taken, they haven’t taken it. So the question becomes what exactly do you see the function of politics being? Is it to build a democratic consensus to do the things that you want to do? Or is it to build a wall around your little political community and cast out the unbelievers? I feel like so much energy is spent on this overactive ideological immune system, trying to identify internal impurities and purge them. It’s shit.”

Astrology or Astronomy

“Neither, if I can help it.”


“I guess I like a Socratic vision of what philosophy is more than other visions — even if he is annoying. I love the framing device in Socratic dialogues where he’ll strike up a conversation with someone on the way to the courthouse and say, ‘What is justice exactly?’ Some people need to have their certainty deflated. When you’re transgender and online, everyone has their idea of what gender is, or what sex is, and so you have no choice but to act like Socrates. Because it’s such a complicated question, you can’t just correct them and be like, ‘No, actually gender is this.’ We don’t know what this is. No one knows that. It’s like justice. There’s no simple answer.”

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Hawaiian Shirts

“I’ve been watching Internet fascists pretty closely for maybe five years, and one consistent theme with them is that they’re always seeking to attach fascist ideology to these very arbitrary cultural signifiers. The more absurd, the better. Frogs, milk, the okay sign, Hawaiian shirts, clowns — I don’t know if there’s a master plan, or if it’s all kind of spontaneous and disorganized, but there’s actually a kind of tactical genius to it. The things they’re saying are deeply taboo in our society. Even far leftists can just organize in the open, but if you’re a far-right, white nationalist, this has to go on in code, so people are like, ‘Why would we need to apply hate laws to these people? They’re wearing Hawaiian shirts!’”

New Atheism

“The alt-right, the manosphere, incels, even the so-called SJW Internet and LeftTube all have a genetic ancestor in New Atheism. It was initiated in books by Sam Harris, Richard Dawkins, Christopher Hitchens, and Daniel Dennett, but the Internet part of it became the blueprint for a lot of future online movements. Particularly in the Anglosphere, people would kind of realize, ‘Oh, I’m the one atheist in my small town, and I erase the geographical difference and create a community that is actually like a global network as opposed to a physical one.’ Looking back I can see, like, the seed of what would become some very reactionary stuff. A lot of this was very Islamophobic. Then in 2011 you saw this feminist kind of schism after Rebecca Watson made a video about being sexually harassed at an atheism conference. A lot of the prominent men in the community reacted to this as if it was, like, a ludicrous outrage. ‘The feminists have gone too far. We’re not even allowed to flirt in elevators at our own conferences. How am I supposed to get laid?’ It led to this SJW, anti-SJW schism that also happened in a lot of, like, nerd cultures — video games obviously ripping it apart in 2014 with the Gamergate thing. The idea that this was about whether god exists has faded so far into the past that you almost can’t remember there was a time when this was the main thing we were arguing about.”


“Baltimore is very hipster. The best you can do is look as bad as possible. It’s a kind of anti-New York in that way.”


“I like her a lot. She’s a woman who is probably one of the most progressive people in Congress, so she’s obviously going to be despised by everyone, not least of all the left. It just doesn’t surprise me anymore, the immense amount of pushback we give to the people who are actually getting up every morning and doing the work. The standard is impossibly high. I feel like I’ve been through this myself within the trans community, where I’m largely hated, partially because I broke into a more mainstream audience. There’s a sense of like, ‘How could you possibly even understand us anymore? You’re a different category now.’”

Jordan Peterson

“People want to be told what to do. I think that’s part of the essential appeal of Jordan Peterson. People want a domineering life coach to step in and say, ‘Here’s what you’re going to do.’ I find this in my own audience. They call me Dark Mother. They want a six-foot transsexual to step on their throats and tell them what to believe. That’s what everyone wants.”


“There was a time when I said I made leftist propaganda, but that was always kind of ironic. What I aim to do is invite people to engage at a more human level with these ideas. That’s one thing I hate about the ‘destroyed with facts and logic’ discourse — it’s just boring. Who cares about a conversation where the goal is destruction? If I wanted destruction, I may as well watch jousting.”

The Stock Market

“I have no idea what the stock market is. I barely know what money is. To me, it’s more mysterious than astrology. It’s like witchcraft for rich people.”

Hope or Cope

“I think you have to hope on some level, otherwise you start to break down. In the last five years, I had a lot of my hopeful assumptions challenged. I grew up thinking the moral arc of the universe bends toward justice. Obama in 2008 was the first election I voted in. I really thought this was a massive moment for America. I did not see Trump coming, or how the Internet would go from being this progressive forum of reason and science where we were so pretentious — a new Parisian salon where we were the new Voltaires arguing about atheism online! — only to see that degenerate into the most barbaric form of racism combined with growing economic inequality. It’s terribly disillusioning and makes you wonder, is history just a cycle of rise and fall? Well, yes, in some ways. But you also have to think back on World War II or the Cuban Missile Crisis or the Black Plague to remember how bad things have been. This is not even close to the low point for humanity. I think that a more intelligent hope can grow out of this — as opposed to a lazy hope based on complacency and the assumption that things are just going to get better. Instead it’s that things can get better, but we have to make them get better. I think that’s the more mature type of hope to feel.”

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