Natalie Wynn : The Oscar Wilde of YouTube Fights the Alt-Right with Decadence and Seduction

 

To call Natalie Wynn a YouTuber seems like a terrible understatement. On a platform awash in makeup tutorials, guys playing video games, horrible comedy and conspiracy theorists, Wynn – whose YouTube channel is called ContraPoints – is someone truly original: a provocateuse, a video essayist and a warrior against the alt-right in ways you would never expect.
 
Her videos are political in nature but feel like theater, involving many costume changes and references to philosophers and academic texts. She can switch from discussing Taylor Swift to Wittgenstein with the snap of a fan. Sharp and funny, she’s a comedian who wields her wit in the service of exposing bigotry and making people examine their own biases.
 
She also happens to be a trans woman, and often talks about trans identity and rights. She’s unafraid of not fitting into anyone’s idea of what she’s supposed to think, and that catches her a fair amount of flak.
 
Millions of people know this already. ContraPoints, which launched in 2016, has more than 1.3 million subscribers. Her videos over the last few years – on cancel culture, on the conservative author Jordan Peterson (whose image she speaks to directly from the bathtub, referring to him as “daddy”) – have attracted tens of millions of views. Her 2018 video about incels, in which she manages to get us to contemplate their pain while still raising an alarm about their unbridled misogyny, generated 4m views alone. All of this has made it possible for her to live on the funding of the more than 13,000 fans who donate to her Patreon account (she doesn’t do ads or endorsements).
 
I traveled to Baltimore on a grey, muggy spring afternoon to visit Wynn at her large, and largely unfurnished, four-storey Victorian townhouse (a rental). The house goes with a certain 19th-century feel projected by Wynn’s arch internet persona – you can imagine her sipping absinthe with Oscar Wilde – but the woman who came down the stairs to greet me looked like a blonde 1970s icon: sort of Marianne Faithful circa 1971.
 
Wynn, 32, is tall, slender and as pale as moonlight. She was wearing light-blue jeans and a sheer, long-sleeved top. Her manner in person is the opposite of the brassy, sassy dame you see in her videos; she’s soft-spoken and doe-like, with big brown eyes. We went and sat in her high-ceilinged kitchen upstairs and talked for three hours while snacking on raspberries and blueberries.
 
Days before I came to see her, the Texas state legislature passed a bill that made providing gender affirming health care to transgender minors “child abuse” – one of many attempts in that state and around the country to prevent transgender kids from transitioning before their 18th birthday.
 
In 2021, 33 states have introduced more than 100 bills aiming to curb the rights of transgender people in general, a record-breaking year for such legislation. These bills come in the context of an increasingly hostile climate for trans Americans, where 28 transgender and gender non-conforming people have been killed this year – nearly all Black and Latina trans women. Advocates for LGBTQ rights say that these bills have contributed to transphobia and violence against the trans community.
 
Wynn seemed troubled by how this new Texas bill was going to affect trans kids and their families.
 
“It’s difficult to talk about this topic because most people don’t know that much about it,” Wynn said in her gentle way. “I think the average person hears ‘transgender medicine and children’, and that doesn’t seem like a good idea because what they’re envisioning is, like, genital reassignment surgery, which is almost never performed on people under 18.
 
“Most of the time, what we’re talking about is puberty blockers,” she said, “which are pretty well-tested drugs that are used to delay the onset of hormonal puberty. Basically, kids who use them end up needing less surgery later. Life is easier for them. A lot of people have this concern, ‘Oh, how could you possibly know when you’re 12 or 13? Why not just wait until they’re adults and let them decide?’ Well, for some kids, they’ve known since they were five, and this is urgent for them. If you have a kid who for years has had gender dysphoria, this is a persistent thing. If you take those kids and you won’t let them transition, it’s torture.”
 
“I think that anyone should be able to imagine what it would be like to go through the wrong puberty,” Wynn added. “If you’re a woman, imagine that your body’s getting hair and your voice is dropping … You’re basically creating refugees of these families who have to go to other states in order to take care of their children.”
 
“It’s very upsetting,” she added.

 
One of the hallmarks of Wynn’s rhetorical style is her ability to get her viewers to see things from another person’s point of view; which in the case of trans children hits close to home, although she says she didn’t know she was trans herself until later in life. “I was not a trans child,” she told me. “I wouldn’t say that I was a girl trapped in a boy’s body. I was able to live as a boy. Being a boy was OK, but being a man wasn’t.”
 
Her journey of self-discovery has been a running theme on her channel, often presented in humorous, self-deprecating ways that seem designed to help the viewer relate to her struggle. One can imagine the dramatic shifts in her own identity may be partly why she balks at cancel culture.
 
She was the subject of a cancellation campaign herself in 2019, when she became the target of a wave of harassment after her video Opulence, which attacks consumer culture and our obsession with wealth, used a voice-over from Buck Angel, a transsexual porn star who had in the past made statements considered offensive by some in the transgender and non-binary communities.
 
“He has a lot of outdated and grumpy opinions about trans topics,” Wynn conceded, “but to me he’s still some kind of legend.
 
“If you don’t fit into the social justice warrior idea of the checklist of opinions that you are allowed to have as a trans person, you might face punishment,” she went on. “One of the things I really don’t like about my own generation is the hyper-moralism of it. It’s like this extreme Spanish inquisition mentality that we have on social media, of trying to detect the signs of heresy and root it out.
 
“I think a part of it also has to do with me having succeeded as a trans woman … I know it’s gauche to be like, ‘Haters and losers are just jealous of me,’ but succeeding as a trans woman, it’s like you went to a low-income high school and then you’re the one who goes to Harvard Law. The other people in the high school are going to have feelings about it.
 
“The whole internet is about jealousy,” she continued. “It creates such animosity between people because it’s all about people envying each other. It’s so unhealthy in every possible way. I’m working on a video about this – envy – which is an interesting topic because of social media, which is all about promoting envy and making people unhappy with what they are and what they have.” She said she’d been reading up on Buddhism in preparation.
 
Wynn was born in Arlington, Virginia, and grew up in a nearby suburb. Her mother is a doctor who practices geriatric medicine; her father a psychology professor. “For the first 20 years of my life,” she said, “I was entirely interested in music.” She attended Boston’s prestigious Berklee College of Music. A shiny grand piano sits in the living room of her Baltimore house. “I still play almost every day,” she said. “Now it’s for pleasure, but when I was younger it was clearly some kind of escape.”
 
“I was OK until I was 14 or 15,” she said, but then she started having some trouble. She was sent to mental health professionals who at various times diagnosed her with depression, bipolar disorder and ADD, among other things, for which she was prescribed Zoloft, Klonopin and other drugs. She now questions those mental health assessments and is no longer taking any psychiatric medications.
 
“One thing I was treated for that I think is nonsense,” she said, “is I was diagnosed with OCD when I was 15. The reason for that was that I was spending too much time on grooming, they decided. Meaning like hairstyling and things. That, to me, is gender enforced through psychotherapy. I strongly disagree with that, because if I had been a girl, I don’t think anyone would have been concerned that I was spending half an hour a day on cosmetics … Gender is very aggressively enforced on teenagers.”
 
After Berklee, she became a philosophy major at Georgetown, where she started exploring her attraction to women’s clothes in a more public way. “I would cross-dress in bars. It was fun, although a lot of alcohol was involved,” she said, smiling wryly. “I would paint my nails and do makeup and stuff. By the time I was in grad school” – at Northwestern, where she pursued a PhD in philosophy – “I was 25. I wasn’t passing as a woman or anything. People still recognized that I was a man.”
 
Wynn recalled a woman in her department who was a “terf”. “She told me that I needed to get psychiatric help because of the makeup and nail polish. I think she was very hostile to any feminine ornamentation, period, and viewed that as the dressings of male oppression forced upon women.”

 
Wynn’s ability to see the other person’s side of things often extends to those who have hurt her as well. “I always sympathize with these people,” she said. The woman at Northwestern “is not a happy person”, she said. “I feel bad for her … I think there’s a lack of understanding about male femininity and what that means in our culture and how it’s treated. Men wearing makeup is not appropriating female culture. There’s no such thing as female culture. Gender is within a culture, and gender mandates categories of existence, I guess, and it forces you into one based on the sex assigned to you at birth.”
 
It’s stunning to see Wynn’s talents at work in her video JK Rowling, posted in January, which has gained nearly 3.5m views. In the video, Wynn – who for most of it is dressed as a witch, a sardonic nod to Rowling’s billion-dollar Harry Potter franchise – takes up the question, much discussed on Twitter, of whether Rowling is transphobic: a question ignited by some of Rowling’s own tweets, as well as an essay she wrote in 2020.
 
Wrapped in this question is also the question of whether Rowling should be cancelled. Wynn’s answers to these questions seems to be yes … and yet, no; she seems less interested in cancelling Rowling – whose books she says she enjoyed as a child – than in prompting her viewers to consider the possibility of their own lurking transphobia.
 
“That essay that [Rowling] wrote,” she said, “honestly reads to me as a cry for help. She talks about her own experience being sexually assaulted and having never spoken about it before, and her own difficulties with gender and bad feelings growing up. All this is associated in her head somehow with trans people. To me, I see trans people as a weird outlet for this pain that she’s harboring and needs to find something else to do with.”
 
And what would she say to those who argue that someone like Rowling should be cancelled for the harm she’s done by spreading her views? “If we can criticize people constructively,” Wynn said, “there’s a chance that these moments could actually educate people and potentially help the person that we’re mad at transform themselves. I try to take a more humanistic perspective when it comes to the topic of bigotry.”
 
Wynn started making videos in 2008, when she was 19. She made videos of herself playing the piano and talking about atheism, a former subject of interest. But it wasn’t until the misogynistic online harassment campaign Gamergate happened, in 2014, that she started to think about using YouTube as a political tool.
 
It was scary to her, because no one seemed to be speaking against the villains of Gamergate. “It felt like a rumbling. And, in retrospect, I see that it was the earth shaking as Trumpism approached. YouTube just exploded with rightwing content. I felt I ought to do something about it, and I also felt I could. I started recognizing I have the skillset to step in.”
 
She developed her style, posting a number of videos before launching ContraPoints in 2016. She had dropped out of grad school by this time and moved to Baltimore for a relationship with a man that didn’t end up lasting.
 
“I went through a period of deluding myself into thinking I was a heterosexual woman,” she said. “It’s easy to fit in that way, I guess. I was figuring it out. There was a period where I was like, no, I’m just a man who likes feminine things. Then there was a period where I identified as gender-queer – non-binary basically. At some point, I realized I want to actually medically transition, and I was like, OK. That’s when I changed my name and started identifying as a trans woman,” in 2017.
 
Last year, she made a video entitled Shame, in which she came out as a lesbian. “How do I put this delicately?” she says in the video. “Your humble hostess is a total les.”
 
“I’m not the same person I was five years ago, or even a year ago,” she told me. “But then,” she asked, “who is?”
 
‘The internet is about jealousy’: YouTube muse ContraPoints on cancel culture and compassion. By Nancy Jo Sales. The Guardian, June 17, 2021.

YouTube has gained a reputation for facilitating far-right radicalisation and spreading antisocial ideas.

 
However, in an interesting twist, the same subversive, comedic, satiric and ironic tactics used by far-right internet figures are now being countered by a group of leftwing YouTubers known as “BreadTube”.
 
By making videos on the same topics as the far-right, BreadTube videos essentially hijack Youtube’s algorithm by getting recommended to viewers who consume far-right content. BreadTubers want to pop YouTube’s political bubbles to create space for deradicalisation.
 
Pivot to the (political) left
 
The name “BreadTube” has its origin in anarcho-socialist book The Conquest of Bread, by Peter Kropotkin. The name emerged organically as a more comedic alternative to the name “LeftTube”, and captures the dissident leftwing nature of the creators it encompasses.
The movement has no clear origin, but many BreadTube channels started in opposition to “anti-SJW” (social justice warrior) content that gained traction in the mid-2010s.
 
The main figures associated with BreadTube are Natalie Wynn, creator of ContraPoints; Abigail Thorn, creator of Philosophy Tube; Harris Brewis, creator of Hbomberguy; and Lindsay Ellis, creator of a channel named after herself. Originally the label was imposed on these creators, and while they all identify with it to varying degrees, there remains a vibrant debate as to who is part of the movement.
 
BreadTubers are united only by a shared interest in combating the far-right online and a willingness to engage with challenging social and political issues. These creators infuse politics with their other interests such as films, video games, popular culture, histories and philosophy.
 
The current most popular Breadtuber, Wynn, has described her channel as a “long theatrical response to fascism” — and a part of “the left’s immune system”. In an interview with the New Yorker, Wynn said she wants to create better propaganda than the far-right, with the aim of winning people over rather than just criticising.
 
Euphemisms, memes and “inside” internet language are also used in a way that traditional media struggle to replicate. The Southern Poverty Law Centre has referenced BreadTubers to help unpack how memes spread among far-right groups, and the difficulty in identifying the line between “trolling” and genuine use of far-right symbols.
 
BreadTubers use the same titles, descriptions and tags as far-right YouTube personalities, so their content is recommended to the same viewers. In their recent journal article on BreadTube, researchers Dmitry Kuznetsov and Milan Ismangil summed up the strategy thus:
 
    “The first layer involves use of search algorithms by BreadTubers to disseminate their videos. The second layer – a kind of affective hijacking – revolves around using a variety of theatrical and didactical styles to convey leftist thought.”
 
What are the results?
 
The success of Breadtubers has been hard to quantify, although they seem to be gaining significant traction. They receive tens of millions of views a month and have been increasingly referenced in media and academia as a case study in deradicalisation.
 
For example, The New York Times has reported deeply on the journey of individuals from the far-right to deradicalisation via BreadTube. Further, the r/Breadtube section of Reddit and videos from all BreadTube creators are littered with users describing how they broke away from the far-right.
 
These anecdotal journeys, while individually unremarkable, collectively demonstrate the success of the movement.
 
YouTube’s algorithms are a problem
 
The claim that YouTube helps promote far-right content is both widely accepted and contested.
 
The central problem in trying to understand which is true is that YouTube’s algorithm is secret. YouTube’s fixation with maximising watch time has meant users are recommended content designed to keep them hooked.
 
Critics say YouTube has historically had a tendency to recommend increasingly extreme content to the site’s rightwing users. Until recently, mainstream conservatives had a limited presence on YouTube and thus the extreme right was over-represented in rightwing political and social commentary.
 
At its worst, the YouTube algorithm can allegedly create a personalised radicalisation bubble, recommending only far-right content and even introducing the viewer to content that pushes them further in that direction.
 
YouTube is aware of these concerns and does tinker with its algorithm. But how effectively it does this has been questioned.
 
Limitations
 
Ultimately, BreadTubers identify and discuss, but don’t have the answer to, many of the structural causes of alienation that may be driving far-right recruitment.
 
Economic inequality, lack of existential purpose, distrust in modern media and frustration at politicians are just some of the problems that may have a part to play.
 
Still, BreadTube may yet be one piece of the puzzle in addressing the problem of far-right content online. Having popular voices that are tuned into internet culture —and which aim to respond to extremist content using the same tone of voice — could be invaluable in turning the tide of far-right radicalisation.
 
Meet BreadTube, the YouTube activists trying to beat the far-right at their own game. By Alexander Mitchell Lee. The Conversation, March 8, 2021. 

Natalie Wynn knows that people can change. After all, she sometimes jokes, she was a “male alcoholic” until 2017. A 32-year-old trans woman, she’s now a wildly popular political YouTuber. Her channel, ContraPoints, was a cultural bright spot of the Trump era, and she may be one of the few people in the left media who can credibly claim to persuade her opponents on occasion. Her videos are also—in a left-media ecosystem of scolds and ascetics—a lavish pleasure to watch.
 
I met Wynn over Zoom just after the Capitol riot and before Joe Biden’s inauguration. In her videos, Wynn’s aesthetic is elaborate and campy, her speech theatrical and well-performed, her look one of high glamour. But like most iconic performers, in person her beauty was simpler. Her makeup was precise and inconspicuous. She wore a black, lacy, floral blouse and her hair in a bun. She spoke with a bit of girlish uptalk and sometimes rambled excitedly.
 
Though Wynn’s channel—and fame—are less than five years old, her fascination with YouTube goes back much further. More than a decade ago, she recalled, she was “embarrassingly interested” in New Atheism, one of the first political subcultures to have a major YouTube presence. A militantly anticlerical movement whose best-known adherents were Richard Dawkins, Sam Harris, and the late Christopher Hitchens, New Atheism represented a backlash against the George W. Bush presidency and the September 11 attacks. As a reaction to religious fundamentalism, New Atheism was attractive to many, like Wynn, who leaned left. But it didn’t take long, she said, to become disillusioned with those “sexist Islamophobes who think they are the most rational people since Voltaire.”
 
While an undergraduate at Georgetown, Wynn drifted away from evangelical atheism. “I’m proud of myself that I was only 22 when I realized atheism was cringe,” she laughed. But she kept watching YouTube videos, and about six years ago, she noticed something disturbing happening to her former intellectual community. Because she had once subscribed to New Atheist channels, YouTube’s algorithm was feeding her content that the predominantly white male online groups had since embraced. “We had gone from ‘Creationists DESTROYED with facts and logic’ to ‘Feminists DESTROYED with facts and logic’ to ‘White genocide is happening. We need to defend the race,’” Wynn said. Her old online circles were flirting with fascism and white nationalism. “It was alarming. And no one seemed to be talking about it. No one seemed to be resisting it.”
 
At the time, the mainstream media appeared titillated by the growth of the alt-right, publishing fawning profiles of Richard Spencer as the “dapper hipster putting a smile on white nationalism,” Wynn said. There were a few left voices on YouTube, mostly a handful of feminists whose earnest videos were the targets of mass-abuse campaigns by the right. On Twitter, “SJWs”—an Internet acronym for “social justice warriors,” or people known for calling out others for breaches of political correctness—preached to the choir at best, and at worst enraged even their sympathizers with their admonishing, hectoring style.
 
Wynn, who began posting videos on the ContraPoints channel in 2016, portrayed this discursive nightmare in a 2017 post titled “Debating the Alt-Right,” in which Jackie Jackson, a “classical liberal” talk-show host, moderates a discussion between “prominent tweeter and author” Saul Salzman and Fritz, a genderqueer neo-Nazi alt-righter. Salzman won’t engage with the Fritz’s ideas; he simply berates Jackson for even allowing the Nazi on the air. Fritz denies being a Nazi, remains polite, and gaslights hilariously—“Well, who hasn’t, in a spirit of irony and exuberance, dressed up as a Nazi once or twice?”—as Salzman grows increasingly outraged. Jackson takes her alt-right guest’s views seriously and reproaches Salzman for calling Fritz a Nazi. In the end, all assertions unchallenged, the Nazi wins, and in a nod to Rhinoceros, Eugène Ionesco’s 1959 absurdist drama about the rise of fascism, Salzman has a vision of Jackson, her head transformed into a rhinoceros’s head, as Fritz looks on approvingly. (In Ionesco’s play, the main character is criticized for pointing out that everyone around him is turning into a rhinoceros—yet in the end, he’s the only human left.) The sketch dramatized the problem that Wynn set out to address on ContraPoints: So many on YouTube seemed either to be becoming Nazis or were complicit in denying the fascist presence.

 
Another early video features Wynn pretending to have a conversation with The Golden One, a Swedish Nazi YouTuber and bodybuilder with more than 110,000 followers. In it, she performs a naive insouciance to show the absurdity of his racist and masculinist ideology, and the video culminates with her asking him how to become an “alpha male” and then pouring milk all over her face. “Those early videos had such an unhinged energy to them,” Wynn recalled. And they were unique on left YouTube at the time. “It’s just a very different approach from being like”—here she adopted a quavering millennial voice—“‘This is literally fascism and, like, I’m very upset that you would say this.’”
 
Instead, she continued, “my stylistic choice was to out-edge the edgelords.” ”Edgelord” is Internet-speak for a person espousing deliberately shocking or offensive views, and while the term is a derogatory one, in the early Trump years, “edge” was the best way to compete in the attention economies of YouTube, Twitter, and Reddit. This is partly how the alt-right became such a formidable cultural and political force. As Susan Stryker, a trans activist and scholar of trans history, politics, and culture at Mills College, told me, “The sensibility of the so-called alt-right or populist right is, ‘Hey, we’re going to own the libtards, and they don’t even get that we’re making fun of them.’ Then for Natalie to say, ‘Dude, I see you, I understand your style, I’m just going to flip it back on you’—that was brilliant. The idea of an aesthetic intervention, not just an argumentative intervention, was genius.”
 
Wynn’s approach has been a huge success. In 2019, she asked on Twitter whether her work had helped people to change their minds, and numerous viewers spoke up with their stories. She regularly hears from people who say they were on the alt-right and that her videos helped convince them to move left. Some have become her friends. As a result, she said, she has people in her circle who were “wearing MAGA hats five years ago.”
 
“You’re going to laugh when I say this,” ventured Steve Duncombe, a professor at New York University and author of the recently rereleased book Dream or Nightmare: Re-imagining Progressive Politics in an Age of Fantasy, “but hear me out: ContraPoints reminds me of Franklin Roosevelt’s fireside chats.”
 
In FDR’s time, explained Duncombe, who is currently researching pro-New Deal propaganda, radio was “filled with snake oil salesmen…quacks and demagogues and all sorts of trashy stuff,” just as YouTube is today. FDR’s radio addresses were effective because “he respects that the audience for radio has the capacity to think and reason.” Wynn, Duncombe added, “understands the medium of YouTube” and also knows its audience can think deeply about gender and capitalism. She can therefore speak directly to a public that wouldn’t have encountered these ideas in any other way.

ContraPoints conveys a belief in the power of logic and reason but also the emotional intelligence to know they are not enough. Wynn understands that opinions come from a deeply affective place, often a raw and lonely one. In a video on incels (short for “involuntary celibates,” heterosexual men who can’t find women and whose misogynistic rage often leads them to far-right politics), Wynn delves into the pain and self-hatred of these Internet communities, empathizing as someone who has spent time with alienated men but also as a trans woman, a member of a marginalized group familiar with rejection and insecurity.
 
The left YouTuber Caleb Cain, formerly an alt-right YouTuber, has credited Wynn with his political conversion, citing her empathy for the disaffected young men like himself in her audience, when most on the left just wanted to denounce him for being racist.

 
In addition to such political triumphs, the financial success of ContraPoints is every casual YouTuber’s dream: Wynn no longer has to have a day job. With 13,595 Patreon supporters at the time of this writing, she’s able to live comfortably in Baltimore and make increasingly high-production videos.
 
Part of her success is due to her aesthetic. “Thinking back to the cringiest part of my life, one of the things I liked about reading Christopher Hitchens—even when I thought he was being an asshole, as he often was—is that he had this style of writing that was somehow charming.” She aspires to that irresistibility in her own work. Even if viewers disagree with it at first, they may not hate it if they fall in love with the style. She wants her video essays to be about “more than being right,” Wynn said. “It’s also about finding pleasure even in the argument itself.”
 
This aesthetic is not just about humor, though the jokes are central. Wynn is a classical pianist—in addition to dropping out of Northwestern’s PhD program in philosophy, she also attended Boston’s Berklee College of Music—and sometimes plays in her cinematically opulent videos. (Political YouTube is normally so visually dull that it’s often unclear why it needs to be a visual medium at all.) Wynn offers much for the viewer to see, citing a range of influences that include music videos, David Lynch, fashion advertisements, and “weird old VHS recordings of drag shows in New York in the ’80s.”
 
“No one’s really that original,” she added, “but what makes an artist boring and derivative is when they have too few influences.” What an artist ideally wants, she explained, is for the viewer to ask, “What the fuck is this combination of things I’m looking at?”
 
Wynn doesn’t just stand out on YouTube; she laments the dour solemnity of the left more generally. “One thread within leftism that I’ve always kind of hated is this: There’s this moralistic almost-puritanism. Sometimes there’s this suspicion of glamour—a suspicion of beauty, even—because that’s seen as decadent and bourgeois. And I hate that. I much prefer the Oscar Wilde division of leftism. Part of what makes human life worth living is not simply having enough food but…aesthetic excess.”
 
We talked about this renunciatory quality to left culture and how it hasn’t always been this way—remember sex, drugs, and rock and roll? So much about the 1960s and ’70s counterculture was, as Wynn put it, an “artistically daring celebration of life.” In one of her videos on capitalism, she makes clear how her love of luxury fits into her leftist economic vision. “Actually, champagne socialism is good,” she tells viewers. “But I’m not talking about the champagne classes becoming socialist. I’m talking about redistributing the goddamn champagne.”
 
Another reason Wynn is such a successful left-media creator is her acute awareness of her audience. “When I started making these videos, there was no such thing as LeftTube,” she said, “and so I was making videos for RightTube. I was gaining followers by conversion.” Even now, she wants to reach TERFs (trans-exclusionary radical feminists), the alt-right, and men on the verge of becoming alt-right.
 
Yet as her audience has grown among the already converted—trans people, liberals, the left—her prominence sometimes draws criticism and even cancellation, a theme she’s addressed in her videos. This can be painful. Wynn is used to personal and disturbing online attacks. Sometimes they come from transphobes or Nazis, which actually makes them easier to handle than criticism from the left, she said. “It’s in some ways less psychologically hurtful, because it’s like, ‘Well, I’m making the Nazis angry.’ There’s a sense of a valiant victimhood that comes with that.” But when the left tells her, “‘Oh, you’re a horrible person, you’re just a rich Karen profiting off of dead trans women’—these crazy things that leftists sometimes say to me bother me more.”
 
Yet Wynn told me she’s also learned from the critiques. As her audience has grown, she’s come to understand that the larger platform entails some responsibilities. She used to feel “entitled,” she said, to state her opinion, whatever it might be. A specific incident about a year and a half ago changed her mind. After Wynn tweeted that she didn’t like being asked what pronouns she uses, the Internet blew up in rage: Many trans, genderqueer, and nonbinary people have been fighting for years to make asking about pronouns a common and easy matter of etiquette. Wynn said she now realizes that “I don’t get to tweet that and have it just be an opinion. That’s not the effect it has.” The effect of that tweet, for example, might have been to further marginalize anyone who wouldn’t want their pronouns assumed.
 
It could also suggest to the cis public that pronouns don’t matter or that asking about them might even give offense. Wynn certainly didn’t intend any of that, but there isn’t much discursive space for her to have “a spicy take” on a subject like this. Anything she says on the subject of trans experience, she acknowledged, “influences the whole public conversation around trans issues because there’s so many people listening to me, especially compared to other trans people.”
 
Asked if she’s a ContraPoints fan, Stryker, the trans studies professor, laughed and said, “I feel like maybe this is part of the story. I need to be very careful.” Although Wynn had made “slight missteps” in her comments about trans issues and nonbinary identities, Stryker said she too was bothered by the social media discourse around these—and many other—issues. “The broader phenomenon of hungry little piranhas feeling like there’s a little blood in the water and just going into a feeding frenzy is a real problem, you know? And it’s hard to talk about, because you don’t want to play into right-wing tropes about left-wing cancel culture.” Wynn herself noted this paradox in one of her videos: Cancel culture exists, she says, but most of the people who complain about it are “dicknuggets.”
 
Wynn said she’d like to see the left-opinion ecosystem—perhaps the left in general—become more tolerant, not so much of divergent opinions but of diverse temperaments. She pointed to the feminist scholar Jo Freeman’s famous essay, “Trashing,” in which Freeman notes that left and feminist communities sometimes mistake a conflict of personality for a political difference. “There’s going to be people who want to be very angry and very scoldy, very outraged,” Wynn said. “Some people…want a safe space where they’re made to feel validated and comfortable all the time. And then there’s people who want to make edgy jokes. All these personalities are going to exist. It’s OK if you personally can’t stand what the other person’s doing. You don’t have to like it. But you have to acknowledge that this is not a political struggle—not really.”

 
For a left-media creator, success can make the question of exactly who your intended audience is a confusing one. “A million people watch my videos every time,” Wynn told me, lowballing the figure (it’s more like 2 million views per video on average, with 1.2 million subscribers to her channel). She did some math and estimated that her videos have about the same audience as 50 consecutive sold-out shows at Madison Square Garden. “Do I have anything to say to an audience that large? And the answer is: Absolutely not.”
 
So what do you do when your viewers could include just about anyone? How do you speak to both the alt-right and the socialist left? In that regard, the subject of Wynn’s first video of 2021 is well-chosen. J.K. Rowling, the author of the Harry Potter series and an outspoken TERF, makes an ideal foil. The author’s success and popularity, as well as her fluency in banal and mean-spirited gender clichés, make her an effective vehicle to explain why TERF ideology is so hateful and paranoid and not simply a benign difference of opinion. The video is on track to become one of Wynn’s most watched, garnering more than 2.3 million views just 10 days after its release.
 
Wynn has no plans to stop doing ContraPoints. “I don’t think anything is going to be more creatively rewarding. I have total creative control,” she said. In answer to a question I didn’t ask, she added that she will “never, ever” run for office—“I’m not the right kind of narcissist for that.”
 
Nor is she seriously considering any medium other than the video essay. She’s been approached to write a book, but she’s not sure it would be worth the commitment. “I’ve spent so much time now learning to do video essays. Why am I going to switch it out when this is what I’ve developed as a skill?” Also, she added, obviously struggling to put this tactfully, “print media, I’m sorry to say, is not as big of a thing as it used to be. YouTube is more of the moment. Because it’s newer, it’s less prestigious. It’s not serious. But that’s always what people say about new media, right?” When novels first became popular, she continued, they were considered frivolous, a decadent feminine distraction. “And now YouTuber is kind of an embarrassing profession. But in 40 years, there’s going to be YouTube studies departments at most major universities. It’ll become serious later. If anything, I enjoy the feeling of being part of something now that hasn’t yet been museum-ified. It still feels to me like this organic form of popular art.”
 
Natalie Wynn Wants to Redistribute the Goddamn Champagne. By Liza Featherstone. The Nation, February 22, 2021.
 

 

The YouTube of today is a vastly different platform from the YouTube of yesteryear. Once characterized by cheesy, poorly-filmed comedy skits and the dominating presence of Vevo, it was a mecca of low-brow humor and cat videos. YouTube’s audience, however, has matured, and so has its content.
 
The video essay is taking over YouTube as a primary form of content on the platform. YouTubers with niche knowledge and impeccable production value are becoming major stars. These YouTubers are smart — they have high level knowledge about topics from critical theory to historical dress — and they perform for the camera in a manner that is entertaining, educational and far-reaching. Many viewers are flocking to YouTube, not just to laugh, but to learn — and the best creators offer both.
 
The video essays I will discuss in this column are nothing short of works of art. They often combine musical score, high fashion and makeup alongside performance and narrative, with sturdy cultural critique and analysis that is both complex and easily digestible. And, perhaps most importantly, they are a hoot to watch.
 
You can’t talk about YouTube video essays without mentioning ContraPoints, also known as Natalie Wynn. She is one of the pioneers of this digital movement toward video essays, and her videos, perhaps best described as “films,” present some of the highest art, critical analysis, skilled performance and humor that the platform has to offer. Wynn delivers all of this surrounded by elaborate sets and beautiful score, while wearing full drag, tipping a 40 oz. to the head and engaging her own hilariously on-the-nose characters through dialogue, a la Plato. If anyone can be described as the intellectual figure of this generation, it’s ContraPoints.
 
Wynn might be described by some as a “classically trained academic.” She studied piano at Berklee College of Music and received a bachelor’s degree in philosophy from Georgetown. She then attended Northwestern to pursue a Ph.D. in philosophy.
 
But this is where Wynn’s career diverged from the traditional academic. She dropped out of the Ph.D. program at Northwestern, saying to Vice News, “The idea of being an academic for the rest of my life became boring to the point of existential despair.”
 
Wynn plays an important role in the contemporary intellectual community — she is no modern liberal. ContraPoints, rather, is a radical leftist. But while many modern left-liberal movements have condemned discourse with “the other side,” ContraPoints has embraced it. She doesn’t shy away from engaging with the arguments of incels, the alt-right, TERFs and public “intellectuals” such as Ben Shapiro and Jordan Peterson (whose visage she hilariously flirts with in a bathtub).
 
This is where Wynn’s academic training combined with her high emotional intelligence make her a powerful public presence. She’s been credited with converting many young alt-right leaning men away from dangerous racist, sexist, transphobic rhetoric. If you’ve ever argued with an alt-righter or “Trumpist,” you might be wondering, how the f*** does she do it?
 
Wynn herself says, “It’s not just about calling someone out and using logic, 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.”

 
Indeed, her critiques are always based on charitable interpretations of the arguments that she addresses, and her combination of philosophical argumentation and sociology has proved to be powerfully effective. For many, it’s difficult to explain to someone why white supremacy is wrong, they just know that it is. But ContraPoints can do it. Her video on the alt right breaks down both the factual incorrectness and negative ethical value of common, normalized white supremacist arguments. She takes the alt-right’s very own arguments and talking points and breaks them down in a clear, charitable and thorough way that makes her critique nearly impossible to dispute. She puts words to concepts that, for many, have been impossible to describe. And she does so in a way that reaches people on every side of every aisle.
 
Contra’s content isn’t just devoted to changing the opinions of alt-righters. She also makes video essays that critique and analyze cultural phenomena (such as “cringe,” “beauty,” “cancelling” and “degeneracy”) with the double-edged sword of philosophical breakdown and extreme drag looks. These videos are fun, but so solid in their argumentation that I was able to use “The Darkness” as a source for my philosophy capstone paper; they have true academic utility. Within these films, she discusses each topic as it pertains to gender, sexuality, behavior, personal beliefs and more. She works out meaningful and thorough descriptions for these topics that provide exquisite foundations for her analysis. She, critically, has perfected the fine art of meaningfully differentiating between expedient political rhetoric such as “trans people are born in the wrong bodies” (phrasing which is not philosophically nuanced, nor true to every trans person’s experience, but is critical to the acquisition of rights for trans people) and more complex metaphysical discussion about gender, sex and orientation which many modern academics shy away from.
 
What puts ContraPoints a step above the rest is her bold, critical and unapologetic nature. She’s not nice. She doesn’t cater to anyone or anything, left or right. She’s not afraid to say, “I am an evangelical transsexual. I don’t want toleration, damn it. I want converts,” and she certainly doesn’t care whether you think she means it or not. She pursues what’s true, what’s expedient and what’s hilarious. And she does it all while dressed as a sexy catgirl.
 
Natalie Wynn’s work is of the highest art, but don’t just believe me, check it out for yourself. Did I mention she’s funny?
 
The Rise of the Video Essay as Art: ContraPoints. Bu Rachel D’Agui. The Stanford Daily, February 16, 2021. 

'"This is an aesthetic century. In history, there are ages of reason and ages of spectacle, and it’s important to know which you’re in. Our America, our internet, is not ancient Athens—it’s Rome. And your problem is you think you’re in the forum, when you’re really in the circus.”

 
With these words Natalie Wynn, through the YouTube channel “Contrapoints,” has emerged as an unlikely hero of the left, debating the populist lurch in American politics and society. Social commentators and philosophers of yore used pens as their swords. Ms Wynn’s 21st century weapons are social media and videos, where she flamboyantly yet thoughtfully argues for freedom and tolerance.
 
Ms Wynn’s videos have together amassed 17m views and around 400,000 subscribers. Her subjects include the alt-right, “incels” (young men angry that they are involuntarily celibate) and Jordan Peterson (an anti-feminist writer). The aim is as much to entertain as to inform. To explore different positions, Ms Wynn creates personas that take part in platonic dialogues with one another.
 
As part of The Economist’s Open Future initiative, we asked her if politics is really a circus or whether it can be pulled back towards the forum. “I’m putting on a show, and that’s why I get so much attention,” she admits. “Is that the way things should work? Probably not. But it’s the way things do work, so I don’t see what choice we have but to act within the parameters of that reality.”
 
* * *
 
The Economist: Social media is bad at conveying nuance. But you seem to make an effort to empathise with the people you disagree with...
 
Ms Wynn: I try to swim against the current as much as possible when it comes to the tribalism that defines the way people do politics on social media, and I try to present myself as an individual and humanistic voice. I’m interested in people, not just factions. I don’t just want to show how somebody might be wrong, I want to know why people believe the things they believe in the first place. I want to understand the mindset that would lead somebody toward the alt-right.
 
And so I tend to be somewhat evasive when I’m asked to nail myself down to one ideological position, because I like to keep myself free and open. I think the way people on the left do things is really ineffective and terrible.
 
The Economist: How so?
 
Ms Wynn: I’ve done several videos that target the strategy, or lack thereof, of a lot of people on the left. There is rhetoric that’s extremely alienating and off-putting. There’s tribalism that makes it very difficult to get in. There’s purity testing that pushes most people out. I think that a lot of the way that leftist spaces work online is designed for 5% of people to be able to be welcomed by them. Meanwhile, right-wing groups are recruiting anyone who wants to get on board with the cause.
 
I have to be cautious because if I tweet one thing critical of progressive movements I get love-bombed by all these right-wing people saying: “You’re so right, it’s so awful that you have to deal with this.” It’s like they have a welcome committee for people who want to sign up for the far right but on the left you almost have to fight your way in.
 
The Economist: Why YouTube?
 
Ms Wynn: YouTube is just where I was. I used YouTube a lot and I watched a lot of videos. And the algorithm, for whatever reason, has a way of just recommending right-wing content, even if it’s not something you’ve sought out. It’s very easy to find your way to anti-feminist, anti-Black Lives Matter YouTube, and I noticed how little progressive content there was on the site. I thought “There’s a hole here,” and “Somebody should do this.” And I thought that person could be me.
 
I was bored with academia and bored of being around people who assume all the same political positions, even though they’re pretty different from what the average American believes. I wanted a more populist agenda and to reach a bigger audience.
 
The Economist: Do social media algorithms invite us to hate each other?
 
Ms Wynn: On YouTube, there’s a right-wing extremism funnel. You start by watching a college student ranting about how dumb feminism is. It’s wrong but it’s not especially sinister. And then three suggested videos later you’re hearing about why we need a white ethno-state to save the race from a Third World invasion.
 
It’s pretty easy for anyone who’s susceptible to that kind of rhetoric to get sucked deeper and further into this kind of thinking. I wouldn't be surprised if something similar happened on the progressive side. We’re all in echo chambers to some extent, and that fosters an intense antagonism. Politics is always antagonistic and tribalistic. But social media puts us in isolated information bubbles. We’re not just disagreeing on politics. We’re disagreeing on reality in very fundamental ways.
 
The Economist: If this is the future of how we consume political ideas, it sounds like a threat to social cohesion.
 
Ms Wynn: In the United States a lot of people don’t believe that climate change is caused by humans. It’s difficult to have political conversations when you can’t agree on basic facts.
 
The Economist: In a recent video you said: “The President of the United States is a reality TV star. This is an aesthetic century. In history, there are ages of reason and ages of spectacle, and it’s important to know which you’re in. Our America, our internet, is not ancient Athens—it’s Rome. And your problem is you think you’re in the forum, when you’re really in the circus.” Do you believe that?
 
Ms Wynn: I do think that it’s a more realistic way of understanding what the biggest platforms of our political circus are like. If you approach presidential debates or political media as if you’re Plato and Aristotle arguing at the agora, then you’re really naive because that’s not what’s happening, that’s not what a debate is.
 
I think Donald Trump shows us politics as spectacle, and it has nothing to do with philosophy or reason or political science or environmental science or anything to do with reality at all. Traditionally we all know that fascism is the aestheticism of politics and the aestheticism of the military. Donald Trump has said that there’s something beautiful about the proper application of barbed wire.
 
The Economist: Maybe he understands something most people don’t.
 
Ms Wynn: He does understand something most people don’t, and he understands the way the media works in a way that most politicians don’t. That’s what I mean when I say it’s a circus. He noticed that we live in a marketplace of attention, not a marketplace of ideas. Trump is masterful in terms of hijacking the conventional norms of journalism because when he’s running for president and says something outrageous, journalists feel like they have to cover it as news. It was basically free advertising for him because in a sense all publicity is good publicity. A lot of the outrageous and supposedly evil things that he says are things that actually resonate with people.
 
The Economist: Should we try to drag politics back towards the forum?
 
Ms Wynn: I don’t know how you could drag it back towards the forum at this point. I don’t see how that could be done. Everyone has to understand that this is a circus and this is how it works, at least until the way the media works changes. What I do on YouTube is—think of this as entertainment. I’m doing some stuff that you could categorise as philosophical thinking. But my priority is to hold the attention of my audience.
 
That’s what I’m thinking about when I’m writing a video. I know that my videos get about 400,000 views each these days, and the reason is because I’m not just a boring talking-head talking about the means of production or dry scientific analysis. I’m putting on a show, and that’s why I get so much attention.
 
Is that the way things should work? Probably not. But it’s the way things do work, so I don’t see what choice we have but to act within the parameters of that reality.
 
The Economist: Since the global financial crisis, liberalism has struggled at the ballot box. Is the right better adapted to the circus?
 
Ms Wynn: There is something about far-right populism in particular that just grabs people on a basic, emotional level. Donald Trump’s messaging and the messaging around Brexit grabs people almost at the level of primordial fear. They set up a big “other”—a scary invasion of immigrants—and they promise protection. The symbols are so basic, like a wall. It plays pretty well in the circus of ideas.
 
But another reason why liberalism is struggling is because a lot of people opposed to the right wing are getting more radical themselves. As the right becomes more extreme the left goes further left. My sense among young people in the United States is that socialis[t], which spent almost a century as a word that was off-limits, is suddenly something that people are calling themselves again. It’s not just a linguistic shift. There is a rising sense of hostility towards American capitalism that hadn’t existed in my lifetime, or even my parents’ lifetime.
 
The Economist: In recent years, free speech seems to have lost a lot of its popularity. Why do you think that is?
 
Ms Wynn: I think that the idea of suppression of free speech has become a major talking point of anti-progressivism in particular. For years this has been the main talking point for a lot of conservatives. Is it true? To some extent it is. When I was a grad student, there was a sense in the department that there was a certain kind of feminism that you just had to agree with. It really felt like you couldn't disagree without being branded as a reactionary.
 
A lot of professors and students feel like they’re not even allowed to ask questions. That’s not good, but I also think that this issue has been blown out of proportion and treated like it’s a massive threat to free speech. College campuses are like strange little incubators that don’t really resemble the rest of the country, so maybe it’s not as universal an issue as it’s presented. Also, a lot of the time free speech, as a talking point, can be used as a dog whistle for “why aren't we letting Nazis speak on campus?” People want to say things that are vicious and hostile towards minorities, and there’s a solid basis for not wanting that kind of thing on campus because it makes life pretty bad for minority students. If you have to be surrounded by hateful rhetoric you’re going to be less open to the idea of speaking out.
 
It’s tricky because you want universities to be places where people can ask questions and where a diversity of ideas can be expressed, but you don’t want the prevailing ideas to be so hostile that they effectively shut some people out of the conversation, because that’s a way of taking away somebody’s free speech. For instance, as a transgender person, if I’m in an environment where I know that lots of people are hostile to trans people, then I don’t feel comfortable speaking out. There’s no easy answer.

 
The Economist: Those threats to free speech probably aren't mutually exclusive.
 
Ms Wynn: I absolutely agree. That’s what makes it so tricky to talk about, because those things are both true at once. On the one hand, the people complaining the loudest about threats to free speech on college campuses often have quite a sinister agenda. The reason they’re complaining about freedom of speech is because they’re complaining about really oppressive ideas being suppressed. But on the other hand, there is a real problem here where there’s an orthodoxy that prevails that is even detrimental to so-called progressive brainwashing.
 
If I want to brainwash someone, they have to be able to ask questions or they’re just going to sit there and think “This is all bullshit but I have to go along with it” and then they go home and go to right-wing YouTube. That’s one reason why I think it’s important to be able to engage with people who don’t agree with us. If you refuse to entertain other ideas, then people who are genuinely curious and don’t have a sinister agenda will be sent into the hands of people who tell them even worse things.
 
The Economist: Was The Economist wrong to interview Steve Bannon as part of our Open Future festival?
 
Ms Wynn: It’s tough for me to provide a definite yes or no answer. Personally, my first impulse is to say it was a bad idea and that you shouldn't have done that. Bannon is the alt-right and people like that are thirsty for platforms. Giving them one can enable them to propagandise for white nationalism. It’s tricky. People like Bannon want any platform they can get for a reason: because it helps them.
 
I understand that this is against what journalism usually wants to do, which is to interview anyone to show the world what they’re about. It can be done well. When I think about Richard Spencer, the mere fact of him being “platformed” sends the signal that these are ideas worth talking about, and it shifts the “Overton window” to the right. Some debates are settled and to constantly have them open to renegotiation is very harmful to a lot of people.
 
For instance, advocates of conversion therapy for gay teenagers—that’s the kind of question that doesn’t need to be debated in my opinion. We know that this is bad. We know that it comes from homophobia and that it wants to basically wipe gay people out of existence. To platform people who advocate this or to include them in a discussion on a big media platform basically signals that this is a valid idea.
 
People like Bannon know how to exploit liberal norms in order to push a very illiberal worldview. It’s quite dangerous, but I’m reluctant to say that you should never talk to somebody like that. There are cases where I’ve seen people do it well, where you expose the person for the terrible thing that they are. But it’s very difficult to do that and most people aren't up to it.
 
The Economist: What does YouTube tell us about the future of politics?
 
Ms Wynn: The biggest thing it tells us is that the traditional gatekeeping that existed into politics and into commentary is gone. Anyone who has enough confidence and charisma and a camera can be the political commentators of the future, and many of them are already the political commentators of the present. It will probably extend to politics. Donald Trump is somebody with no background in politics whatsoever. Is it conceivable that we might have a YouTube president? It is to me. It’s a scary thought.
 
But YouTube is already becoming serious competition for traditional news media—especially when it comes to political commentary. Most of these people don’t have degrees in journalism or editors holding them up to certain standards. There are no fact-checkers. Information and media are becoming unhinged from the grounding it has on older media.
 
In some ways that’s great because that gatekeeping was keeping a lot of people out unfairly. For instance, it’s amazing to see transgender people, who have never had much power in society and have been unable to speak for themselves. If they have enough showmanship, they can get a big audience and speak their truth without constraints. On the other hand, if you have a suspicion of immigrants and a webcam, you can have millions and millions of viewers. That’s something that we’re all going to have to deal with for the foreseeable future.
 
The transgender populist fighting fascists with face glitter. By N.B. The Economist, December 21, 2018.

Hail mortals, I come to thee from my fairy grove to bring thee tidings of great woe,” says a glitter-speckled woman flapping a pair of iridescent wings in the midst of a faux-forest, her otherwise naked body strategically festooned in butterflies. “Western culture is being destroyed — by cucks, and by gender bending, intoxication, and sodomy,” she intones solemnly. “You know, things that have never happened in Europe.”

 
ContraPoints, whose real name is Natalie Wynn, is known for slick, moodily lit YouTube videos that draw hundreds of thousands of views, where she brings a leftist perspective to a variety of hot-button issues — things like structural racism, Marxism, transgender politics, and the alt-right. With a wink, she calls herself “one of YouTube’s leading B-List transsexuals.”
 
For a time, Wynn pursued a PhD in academic philosophy, but she left when she found the academy too stifling and hidebound; in this light, ContraPoints is a gloriously effective act of revenge, redistributing the wealth of knowledge in digestible form.
 
But her affect and persona are what made her brainy, insightful videos popular. More than most of her contemporaries on “LeftTube,” Wynn has a style; her editorial signature is an unmistakably ornate flourish. Her ContraPoints persona is decadent in the mold of Oscar Wilde by way of Weird Twitter: sexily confident and fearlessly indulgent, with orations delivered from plush chairs and scented baths. Her style extends to the postmodern rococo of her set design and the bewildering variety of costumed characters she plays on her show, giving us something like Platonic philosophical dialogues in the idiom of social media.
 
ContraPoints as a character is nothing if not luxuriously indulgent: “sex, drugs, and social justice” promises Wynn’s Twitter bio. It seemed appropriate to sit down for a drink with her — albeit a virtual one. So I poured my Scotch and set about asking her a few questions, particularly about her online persona, her controversies, and her sense of irony — a sharp cocktail of eros and empathy that elevates her political commentary to a singularly powerful plane.
 

 
The tension between persona and person, familiar to all who are touched by even a feather of fame, is evident in Wynn’s work and online presence. She sometimes struggles with the potential conflicts between what she wants to say, the expectations of the fans who make memes about her and deliver her views — sometimes as many as half a million per video — and a diverse transgender community who has come to see her as a representative. The wider left online, energized by a real sense that today’s crises present an opportunity for socialist movements, is also starting to see her as an envoy for the cause; an articulate, attractively cool leftist who’s reaching the digital generation where we live.
 
Nathan J. Robinson, editor-in-chief at the leftist online magazine Current Affairs, writes that what ContraPoints does is “smart … persuasive ... fun. More of this sort of thing, please. God bless ContraPoints. She’s a national treasure.”
 
But such pressure makes missteps costly. Last November, Wynn was harshly criticized by many of her viewers for agreeing to a Vancouver debate at the University of British Columbia’s “Free Speech Club” with Blaire White, a self-described conservative YouTuber who has shared coy tweets with Richard Spencer, enthusiastically supported far right activist Lauren Southern (whose most recent exploits include participating in expeditions to attack asylum seekers in the Mediterranean Sea and ginning up fear about immigrants in Melbourne), as well as Milo Yiannopoulos (whose connections to the extreme right, and actual Neo-Nazis are well documented). She has also donned blackface (which many understood to mock Black Lives Matter, a frequent target —though she has since deleted many of her YouTube videos attacking them) and once posted on Facebook that “if he ain’t Aryan, we ain’t marryin’.” Condemnation was swift, and Wynn was accused of legitimizing a fascist.
 
“I think they are worth speaking to, for a few reasons,” she wrote in a lengthy thread defending herself. “I have conflicted feelings about it myself but have decided to take the risk in order to promote a leftist perspective that I believe at least some of the audience is receptive to.” While some claimed that she was being used as a naive prop by the far-right, she insisted that rather than seeing all her ideological opposites as “hopeless bigots,” that many in their audience hadn’t considered other points of view in any detail.
 
One of the tenets of leftist thought is supposed to be that many popular attitudes are the result not of individual moral defects, but of a collective default way of seeing: "bourgeois ideology," "rape culture," "male gaze" "cis/hetero normativity"
 
        — Natalie Wynn (@ContraPoints) November 30, 2017
 
 
 
In the end, she told me, White “flaked out” on the debate, and Wynn ended up chatting with the moderator to a “pretty small classroom.” But amid the call-outs, she forswore future debates with right wing extremists, almost petulantly, because “my heart can’t take the backlash anymore.” In a subsequent, searching Twitter thread she wrote about how the backlash had forced her to completely rethink her life.
 
“At first, I was confused that anyone could see me as this figure of any importance. But now I think I’m starting to kind of get it,” she told me, before describing fan meetups in the US and Canada where she met over a hundred other trans people who impressed upon her the importance of her role. This, she said, led to newly out trans people looking up to her as an example of confidence and success in transition. “There’s a lot of emotional investment, not in me but in people’s idea of me.”
 
 
“This is the best piece of advice I can give to aspiring YouTubers,” she wrote on Twitter at the time: “your audience are not your friends. They are spectators. Their love is highly contingent. The moment you fuck up you’re dead to them. They do not love you. They love an idea of you.”
 
Eventually the hurt feelings gave way to a new sense of responsibility. “I basically had to radically change the way I behave online,” she tells me. She’s tried to draw a clearer line between her persona and herself, cutting back on revealing personal streams, eschewing flashy public debates, and thinking more critically about how her work will be understood.
 
Confronting the right, she says, is “broadly my mission,” but “the way I go about it has certainly changed.” Beyond that, however, she has come to question the utility of these sorts of one-on-one debates. “A debate,” she told me, “is a very specific kind of performance.” Wynn’s point is well taken; debates rarely test the rigor of ideas, but the strength of one’s pitch. That pitch combines many elements: appearance, style, rhetoric. But “truth” is not required, only a good argument. Though often conflated, these are not the same. A persuasive argument is not necessarily an accurate one; a poor argument is not necessarily wrong.
 
Wynn offered up an example of the latter from her earliest days as a YouTuber: she’d debated Blaire White before, online, well before she herself had transitioned.
 
“Even though I think everything I said is essentially true,” she said, “I looked awkward. I was wearing this awkward pink anime wig and not looking at the camera and just talking like an insecure man. And I’m next to, you know, the conservative shitlord fish-queen supreme,” she said, laughing. “None of this has anything to do with reason, none of this has anything to do with evidence, none of these things people imagine themselves being persuaded by.”
 
The cult of rationality that pervades so much discourse across the political spectrum neglects the role of emotion in our decisionmaking, and, perhaps most urgently, the role of emotional appeal in the success of many neo-fascist movements around the world. Perhaps the most important thing ContraPoints offers us is a sense of what it looks like to combat that vision with something similarly visceral.
 

 

There’s always a moment in her videos that throws you.
 
In the aforementioned episode, “The West,” it isn’t her performance as a glamorously nude faerie queen; instead, it’s her nostalgic reflection on the classic real-time-strategy game Age of Empires, including a bit where the bearded “prophet” from the game magically willed a metaphorical gender transition from male to female. She accompanies this with a flirty lament about The Golden One, a Swedish YouTube personality who mixes bodybuilding with neo-fascism and looks exactly like the ‘roided-out Aryan slab you’d expect.
 
“Ah, The Golden One,” Contra says, “his soul and mine are intermingled. Probably because we both played 1,200 hours of Age of Empires in 1999 and then something went terribly wrong. Fuckin’ 9/11! It used to be such an innocent decision, choosing to play the Franks or the Saracens, and then it became this huge civilizational struggle… and that’s why this guy is a fascist and I grew up to be a woman.”
 
When deconstructing the sludge of alt-right YouTube, Contra consistently and methodically picks apart the first principles of streamers. But she uses a coquettish tone when she talks about The Golden One — a strategy that is as subversive as it is effective. Infinite jest, painfully finite seriousness, all at the expense of a self-serious fascist bodybuilder. “There are things you can say in the voice of a fictional character that you could not explore any other way,” she tells me.
 
As the election of Donald Trump clearly demonstrates, mocking bigots is not sufficient in itself to stop them. Instead, Wynn uses a different tool to humorously undermine her most sanctimonious right-wing targets: seduction. Her video about right-wing self-help guru Jordan Peterson begins with her flirting with him (or a masked mannequin of him, at any rate) at some length, sitting him down in her bathroom so he can watch her bathe while she critiques him. She calls him “daddy.”
 
There’s a lot to unpack here, but in brief, as Wynn puts it, “You [can] respond to a political opponent and have the model of that conversation be seduction. Because usually what you have on YouTube is this very combative posture right? Ownage. Wrecking. Destroying your enemy.” It is, she says, a “toxically masculine posture: the idea that a conversation or an argument is about destroying another person. That’s a terrible thought and a terrible way to have discourse.”
 
It is fun to watch, however, as Wynn notes. Thus, to entertain without giving into that ‘x eviscerates y’ screaming-headline discourse, she turns to seduction. Far from adding to their mystique (could one imagine Jordan Peterson as a sex symbol?) it actually helps chip away at their threatening postures.
 
“I die laughing every time TheGoldenOne is included in your videos,” writes one commenter. That, indeed, is the point. And it’s bigger than just making a funny for its own sake.
 
The strategy captures a dynamic noted by fellow LeftTuber, film critic Lindsay Ellis, in her analysis of the satire in Mel Brooks’ The Producers. She argues that aesthetics of the earnestly anti-Nazi film American History X are eagerly aped by actual neo-Nazis, but the uproariously campy rendition of Hitler’s Germany in The Producers is not. Real life Nazis are not, Ellis notes dryly, singing “Springtime for Hitler.” In the end, despite all the controversy about the film, it hit them where it hurt.
 
Wynn’s strikes as ContraPoints are similarly surgical, and what parses as lighthearted jocularity or inexplicable sexual attraction at first quickly resolves into a virtual pantsing. It’s a prologue to an elegant crash course in the history of postmodernism and why Peterson’s obscurantism makes him difficult to argue with. Calling Jordan Peterson “daddy” and portraying him as a robot lovingly watching Wynn bathe doesn’t ennoble him; it erodes him. That was made clear when Peterson’s sole response to Wynn’s carefully argued video was a mere “no comment,” when he had thundered at and even threatened more earnest (less flirty) critics.
 
Irony is a means rather than an end for ContraPoints. In an era saturated by Dadaist humor on every social media platform, where memes become news, this can seem to be a meaningless distinction. But it makes all the difference. For all of her racy humor, Wynn is no edgelord. Throughout her interview, she was nothing if not deeply sincere.
 
She decries what she calls the “South Park” sensibility, which, as she sees it, holds that “the problem with the world is that some people take it seriously.” It’s a centrist viewpoint, she says, which “the fascists latched right onto and did a great job with, because who cares more than the social justice warriors? ‘Look at them with their signs, their protests, their complaints. Look at these poor, naive, uncool fools caring about a thing and trying to make the world better unironically.’”
 
But at the same time, she observed that irony could be a powerful tool to make people care.

 
 
Wynn is often such an eloquent middle finger to alt-right pretensions that it can obscure the fact that she is profoundly new at this. She’s a streamer whose two-year-old YouTube channel is older than her life as an out transgender woman, the ruptures of which punctuate her videos from the past year as everything from jokes to digressions to whole episodes worth of vein-stripping insight.
 
Her humor can’t be reduced to the discrete block of a “skit” or a throwaway gag; it’s expressively woven into the points she’s making, and only rarely feels like a distraction — as it so often can when late-night comedians clumsily try to join serious topics with zany humor. Where John Oliver’s humor is a non-sequitur punctuation to the meaty topics that he covers on Last Week Tonight, ContraPoints’ form is the content. And in the process she’s just as enlightening as Oliver, more radical, and certainly more elegant.
 
In her recent video “Tiffany Tumbles,” she appears as a satirical character — the eponymous Tiffany — a sassy trans fashion vlogger who dons a MAGA hat and rants about “the Muslims” in between makeup tips. The point of this episode, one of her most elaborate and emotional performances, is to get inside the head of Tiffany to reveal how “how bigotry becomes internalized and how internalized bigotry becomes the alibi of external bigotry.”
 
This sort of exercise in vulnerability is quite unique — even among comedians, who practice an artform defined by self-deprecation. Wynn’s humor folds back on itself into affirmation, after all, which trans people in particular need in a political age where our very existence is held up for debate. And that’s how we come to the semiotics of sucking a trans woman’s dick.
 
About halfway through the Tiffany Tumbles video, viewers get an extended disquisition about the unique contours of transgender sexuality. In the guise of another character, a plaid shirt-wearing trans lesbian named Adria, Wynn discusses why being a lesbian needn’t involve an aversion to penises, because, among other things, a “feminine penis” attached to a woman can involve a physically different experience.
 
“So to start with,” Adria says, “it doesn’t get as hard, it doesn’t really ejaculate, and it has a different mouthfeel. Can we please talk about the mouthfeel? Why is no one talking about the mouthfeel?” she repeats, looking straight into the camera through her clear-framed glasses as the camera zooms in. “Girl-dick is everything soft and smooth.” The irony lies in the confronting vulgarity of this speech, but not in its substance. It’s a sincere report on sexual experience among trans women and trans-feminine people. A woman with a penis is not a contradiction, and she can also offer a distinct sexual experience; none of that invalidates her claim to womanhood.
 
The video is a crescendo for Contra’s cast of characters, nearly all of whom stay on just the right side of caricature. “Anyone who writes fiction strives to show characters as more than one-dimensional,” she tells me. Not so with political satire, she laments, “even though your villains have interiority — they love, they hate, they feel.” She wants to go beyond mockery and the point-scoring of pointing out hypocrisy. “There’s this artistic drive or something in me that impels me to sympathize with villains,” she reflects, “but it’s maybe not a great impulse as someone who wants to do activism as well.”
 
The story she tells about Tiffany Tumbles is a tragedy about self-loathing turning to evil, revealing that potential trajectory in us all. Wynn uses Tiffany to explore the struggles of all trans women in a way that doesn’t excuse that bigotry. It’s a surprisingly affecting tableau of trans sexuality, insecurity, and the quiet desperation we all live with, refracted through the life of a self-immolating woman who sells out her sisters in the hopes of dulling her own pain. Tiffany’s personal hell — revealed through a climactic breakdown scene that Wynn says took her eight takes over three days to film — is framed as a particularly deep circle of infernal insecurity shared by all trans women, including Wynn herself.
 
 
“It’s very personal stuff,” Wynn says about the transness of her videos, which have seen her change visibly before her audience, “and it’s deeply interwoven with political commentary, including great things about my sex life and things about my body, or anxious thoughts I have when I’m trying to fall asleep at night… The deeper target of [the Tiffany Tumbles video] is not Blaire White, but my brain.”'

 
There can be no decadence without the theatrical tragedy of a shattered glass; when the glass falls here, it punctures a scalding scene about the reality of trans existence. Tumbles is alone at night, after participating in a right-wing debate show, drinking herself into a stupor after reading transphobic comments from the very right wingers she’s pandering to. Her cocktail glass shatters as she finally passes out; she’ll face another day as a MAGA vlogger. She lives a lie, but not as a woman. The lie is her tragic belief that her public self-abasement will win her any real affection from anyone.
 
Wynn calls the video “cathartic” — and I felt it too; it was a piece of work that transmutes black humor into searing empathy. It toyed with deeply personal pain that somehow cut deeply to my bone. Tiffany’s anxieties — about dysphoria, her self-loathing, her false belief that she could do anything to stop bigotry being hurled at her — are common to so many of us trans people. Yet the ironic tone, a mixer in a fine cocktail, took the edge off the hard stuff. When pain emerged ungarnished, it was not only more poignant, but expressive for that fact. The wound is real, and the fact that there are no Contra jokes to wrap it up in gives Tiffany’s breakdown a hiss-inducing sting. Through it all, Contra’s irony isn’t just used to wound others, but to expand our sense of empathy.
 
We see it in her latest video, too — a meaningfully fresh take on so-called “incel” communities. Without validating what she likens to a “death cult,” Wynn explores the similarities between the digital self-harm of incels and that of trans women who are early in their transitions, building a bridge of empathy with a noxious group that has produced literal terrorists. She calls their worldview “masochistic epistemology”: “whatever hurts is true.”
 
In the process, she not only helps us understand why incels believe what they believe, but why all of us feel a certain desire to read hurtful things about ourselves online; all this, interspersed with phrenology jokes that Contra links to her own desire to get facial feminization surgery. Speaking to incels, Contra tells them that they use their arguments not as true policy positions, but “as razor blades to abuse yourselves. And I know. Because I’ve done the exact same thing.”

 
Despite the sharpening of her skills as an ironist, and learning how to balance persuasiveness with conviction, that disconnect between Wynn and her online persona remains; it bedevils her as it bedevils all the streamers and microcelebrities who dominate our age. In a recent tweet she observed, with characteristic humor: “BDE [Big Dick Energy] is a really useful concept to me because I’m often asked to describe the difference between my online persona and me as a person. I can’t think of a better way to put it than this: ‘Contra’ has BDE. I do not.”
 
It brings one back to the question of what “BDE” is — a question that’s very much Contra’s kind of philosophy. “A lot of Contra’s BDE comes from what, in real life, would be escalator wit,” she tells me. “After an encounter with a bigot, you think of clever retorts that, in a real confrontation, you don’t have the agility or the courage to produce. Well, Contra has a script and she can fire these things off from the safety of the studio.”
 
Wynn added, “I’m agreeable to a fault. So Contra is like this superhero I imagined that says the things I want to say.”
 
Her views have been influenced by the characters she has created, too. The wildly popular character of Tabby — an anarcho-communist trans cat-girl who sports an ANTIFA patch and wields a baseball bat to smash capitalism — began life as a caricature of radicals that Wynn felt weren’t strategically minded enough. But her audience “resonated with the character,” finding her a “cute and sort of cathartic” presence and, thus, she says, “I’ve switched to portraying her in a more sympathetic light.” Increasingly, Tabby feels like a part of Wynn’s own psyche as she herself has radicalized.
 
In a recent video, when Contra and Tabby were arguing about revolution versus electoral reform, Tabby broached the unsettling possibility that the 2020 presidential election might be “delayed” or canceled outright. “Well,” Contra said, “then I’ll transition into you and become you unironically.” It feels like she’s getting there, certainly.
 
The most notable difference between Contra and the woman who plays her lies in the question of sincerity; in person, Wynn is earnest and agonizes over the utility of her work. Contra, meanwhile, can blithely say into the camera: “Reason; power; truth. These are the kinds of topics that I simply don’t care about.” Alas, she sighs, she supposes she has to talk about them. But after my time with her, I now sense a perceptible wink behind all that affected aloofness and decadent disdain. Committing the cardinal sin of our age, Wynn cares deeply; almost too much.

 
This self-awareness and Wynn’s forceful separation of herself from her YouTube persona has grown naturally out of her online experiences, including the painful ones. Instead of letting her fans pretend that they know the real her just from seeing her work, she has now drawn clear boundaries. Fans aren’t friends, and performance isn’t self. It’s a hard lesson to learn when thousands are watching — perhaps most especially in the moments when you’re actually in the wrong.
 
In our conversation, which sprawled over two hours and change, she was always quick to check herself, describe other points of view fairly, and even criticize herself. But she also remained resolute about critiquing her allies. We had a particularly fruitful chat about the tendency for liberals and leftists to overuse words like “problematic” or “gaslighting” to the point of meaninglessness. Leftists, she warns, are in danger of “entombing ourselves in this paranoid world of purity,” impenetrable to those whose past moral failings were even remotely public — a rapidly expanding population in a world dominated by social media. “How was I able to become a leftist figure on the internet? Well, only because I was nobody.”
 
I came to the interview wanting to ask pointed questions about some of her biggest controversies and criticisms: her abortive debate with Blaire White, her vulnerability to the tactic of “lovebombing” — attempting to influence someone with insincere positive attention — from the alt-right, and her decision to accept an interview with journalist Jesse Singal, an inexplicably frequent commentator on trans issues whose work is regarded by many trans people as hostile to the community.
 
Wynn brought up each of these topics without being prompted. She notes a chronic anxiety among her fans and allies “that I am going to do a face-heel turn… that I’m going to basically go to the dark side and become a fascist or something.” But she clearly pays attention to who responds to her and what their motives might be. She noted that after her warm interview with Singal she was lovebombed by “centrists and right wingers” who offered false comfort over how she was being criticized by other trans people.
 
She’s philosophical about the affair now, regretfully noting that she didn’t know the relevant history behind his story defending a doctor at the infamous Centre for Addiction and Mental Health in Toronto, a state-funded clinic which many trans folk, myself included, have likened to conversion therapy for trans people.
 
She was horrified, later, when she saw Singal’s recent and much-criticized cover story for The Atlantic, a 10,000 word apotheosis of his moral panic about trans kids receiving treatment for gender dysphoria. It’s a popular hobby-horse for media in both the US and UK: scaremongering about an imagined wave of young gender non-conforming cis children being forced by well-meaning doctors to take hormones and have life-changing surgeries.
 
“I cried when I saw that cover of The Atlantic,” she told me. “Because I realize I had been an alibi to this person who’d just written this article for a major glossy magazine with a cover that appears to misgender a trans child twice.”
 
For both Wynn and Contra, her ascent as a major leftist voice on YouTube has been a crash course, one that happened at the breakneck pace of social media, live-streamed in real time. There has been little room for error, none for rehearsal, and too few quiet spaces for this kind of reflection. But it is clear that she’s listened to her left-leaning critics over the last few months, and that she’s a good deal savvier than she’s sometimes given credit for.
 
I’ve been out as a trans woman for a decade now and I feel a certain arrogance creeping upon my thoughts when I’m not looking: that yearning to condescend to newly out trans people, to declaim their lack of knowledge, experience, and, yes, suffering. But talking to Wynn candidly opened a window on what that’s actually like for a trans woman coming out today, before the snap judgment of thousands of strangers in the putrefying swamps of Twitter and Reddit. Above all, it’s a path away from shame that other queer people can follow, not just in terms of her trajectory toward success, but the playful, joyful, and honest way she approaches it.
 
“I carry with me from my male upbringing a sense that femininity is forbidden,” she tells me. “So when I appear on YouTube with forty butterflies glued to my body and glitter all over my face, I have a sense that I’m getting away with something I’m not supposed to. I’m being decadent. I’m enjoying a forbidden pleasure. And that’s fun, and it’s funny. It’s always funny to watch someone shamelessly enjoy something they’re not supposed to enjoy.”
 
“If you’re going to be doing this miserable business of talking to these far-right goons, you might as well enjoy it.”
 
Update 8/27/18: Clarified Wynn’s prior knowledge about the Centre for Addiction and Mental Health.
 
Update 8/28/18: This story has been updated to clarify the characterization of Blaire White.
 
The Oscar Wilde of YouTube Fights the Alt-Right with Decadence and Seduction . By Katherine Cross. The Verge, August 24, 2018.

Contrapoints

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