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The Oscar Wilde of YouTube fights the alt-right with decadence and seduction

ContraPoints is an elegant, whip-smart middle finger to the putrefying swamps of the internet

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“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.

Natalie Wynn in her kitchen.
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 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.

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.

ContraPoints offers us a sense of what it looks like to combat the emotional appeal of neo-fascists with something similarly visceral

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.”

Irony can be a powerful tool to make people care

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 as her character, Tiffany Tumbles.
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 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.

Wynn is an eloquent middle finger to alt-right pretensions

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.”

Wynn as her character, Tiffany Tumbles.
Wynn as her character, Tiffany Tumbles.

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.”

Wynn as her character, Tabby.
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.”

“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.

Natalie Wynn at home in Baltimore.
Natalie Wynn at home in Baltimore.

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.”

“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.