“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 astyle; 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.

Natalie Wynn in her kitchen.

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 magazineCurrent 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, she 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 the ethnonationalist YouTuber Blaire White, who is notable for being one of the few visible trans faces on the extreme right. Condemnation was swift, and she 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 theiraudiencehadn’t considered other points of view in any detail.

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 inmebut in people’sideaof 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.

in her analysis of the satire in Mel Brooks’The Producers. She argues that aesthetics of the earnestly anti-Nazi filmAmerican History Xare eagerly aped by actual neo-Nazis, but the uproariously campy rendition of Hitler’s Germany inThe Producersis 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 makesallthe 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 tomakepeople care.

Wynn as her character, Tiffany Tumbles.

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 onLast Week Tonight, ContraPoints’ formisthe 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.

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.”

Wynn as her character, Tabby.

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.”

“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 of Singal’s coverage of the trans community — including a 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 forThe 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 ofThe 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 outtoday, 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.”


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