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.”