ContraPoints Is Political Philosophy Made for YouTube

In her lushly produced videos, Natalie Wynn brings a rare skill for rational argument and emotional persuasion to one of the most vicious battlefields of the online culture wars.

A still from the ContraPoints video 'The Apocalypse'
A still from the ContraPoints video "The Apocalypse" (YouTube)

Marie, a slender woman wearing white lingerie and glitter-encrusted nails, gets into her bath with a bottle of Moët and calls for her servant Antoine. When the door opens, it’s not Antoine, but another woman in a lab coat and a purple wig. “The Doctor,” as the visitor is known, has come to force Marie to watch an educational video about climate change. The pair argue, insult one another, and eventually encounter a personification of the sea, who’s played as a raunchy cross between Ursula from The Little Mermaid and the child-devouring Cronus of Greek myth.

This is, essentially, the plot of “The Apocalypse,” the latest video from ContraPoints. Created and hosted by Natalie Wynn, the political YouTube channel began as a cult hit and now boasts nearly 400,000 subscribers, having recently garnered attention from mainstream outlets such as The New Yorker and The Economist, and from the podcast Chapo Trap House. The videos are impressively produced: Wynn uses lush sets, moody lighting, and original music by the composer Zoë Blade to forge a distinctive aesthetic that can be described as a kind of high-concept burlesque, drenched in neon. The most spectacular attraction, though, is Wynn herself. While her primary persona is the eponymous Contra, she also plays a cast of visually and ideologically distinct characters. Viewers might see Wynn as a supercilious women’s studies professor insulting Wynn as a transgender cat-girl. Or a submissive Wynn explaining the political theory of hypothetical consent while being whipped by a dominant Wynn. Or a fascist Wynn dog-whistling to an online audience while winning a debate against an academic-historian Wynn on a libertarian talk show—hosted by Wynn. The videos are consistently smart, surreal, and fun to watch.

While Wynn positions herself on the left, she is no dogmatic ideologue, readily admitting to points on the right and criticizing leftist arguments when warranted. She has described her work as “edutainment” and “propaganda,” and it’s both. But what makes her videos unique is the way Wynn combines those two elements: high standards of rational argument and not-quite-rational persuasion. ContraPoints offers compelling speech aimed at truth, rendered in the raucous, meme-laden idiom of the internet. In particular, Wynn has managed the remarkable feat of bringing the spirit of Socratic dialogue to one of the most vicious battlefields of the online culture wars.

ContraPoints was born of a specific political and rhetorical context. In 2014, Wynn noticed a trend on YouTube that disturbed her: Videos with hyperbolic titles like “why feminism ruins everything,” “SJW cringe compilation,” and “Ben Shapiro DESTROYS Every College Snowflake” were attracting millions of views and spawning long, jeering comment threads. Wynn felt she was watching the growth of a community of outrage that believes feminists, Marxists, and multiculturalists are conspiring to destroy freedom of speech, liquidate gender norms, and demolish Western civilization. Wynn created ContraPoints to offer entertaining, coherent rebuttals to these kinds of ideas. Her videos also explain left-wing talking points—like rape culture and cultural appropriation—and use philosophy to explore topics that are important to Wynn, such as the meaning of gender for trans people.

Unlike many others who share her political beliefs, Wynn thinks it’s a mistake to assume that viewers of angry, right-wing videos are beyond redemption. “It’s quite difficult to get through to the people who are really committed to these anti-progressive beliefs,” Wynn told me recently. However, she said, she believes that many viewers find such ideas “psychologically resonant” without being hardened reactionaries. This broad, not fully committed center—comprising people whose minds can still be changed—is Wynn’s target audience.

Usually, the videos to which Wynn is responding take the stance of dogged reason cutting through the emotional excesses of so-called “political correctness.” For example, the American conservative commentator Ben Shapiro, who is a target of a recent ContraPoints video, has made “facts don’t care about your feelings” his motto. Wynn’s first step in trying to win over those who find anti-progressive views appealing is to show that these ideas often rest on a flimsy foundation. To do so, she fully adopts the rational standards of argument that her rivals pride themselves on following, and demonstrates how they fail to achieve them. Here, Wynn takes her cues from Socrates, who was famous for publicly exposing the ignorance of men who thought themselves wise. (Contra frequently alludes to the Athenian in videos, often directly addressing a bust of the philosopher.) Wynn dissects her opponents’ positions, holding up fallacies, evasions, and other rhetorical tricks for examination, all the while providing a running commentary on good argumentative method.

The host defends her own positions according to the same principles. Wynn takes on the strongest version of her opponent’s argument, acknowledges when she thinks her opponents are right and when she has been wrong, clarifies when misunderstood, and provides plenty of evidence for her claims. Wynn is a former Ph.D. student in philosophy, and though her videos are too rich with dick jokes for official settings, her argumentative practice would pass muster in any grad seminar.

While Wynn faults what she sees as the incompetent philosophy of her right-wing opponents, she critiques many of her leftist allies for being bad at persuasion. The latest ContraPoints video dramatizes how people with progressive beliefs often fail to change minds on an issue, even when they have all the basic moral and empirical facts on their side. In “The Apocalypse,” the Doctor forces Marie to watch a video-within-a-video that makes a well-reasoned case for serious action on climate change. But Marie is frustrated: “You want me to go vegan, drive a Prius, and vote Democrat. You’re basically asking me to completely change who I am as a person and become everything I hate.” The Doctor’s response: “Yep, pretty much.” Marie raises some skeptical counterarguments (“Weather changes sometimes”), but quickly abandons them when pressed. Marie is not so much a climate skeptic as a climate indifferentist. She’ll accept the possibility of an apocalypse, but will never give her adversaries the satisfaction of doing as they suggest. Though Marie is a caricature, Wynn’s real target in this video is the Doctor, whose facts-only approach is a logical success but a persuasive failure.

The lesson of the video is that rational argument, even if it “destroys” the opposing position, usually isn’t enough to convince. In one of her early videos, Contra pokes fun at a long series of obscene comments she received that used anal rape as a metaphor for victory in argument. She asks rhetorically, “Is tearing your opponent’s butthole to shreds really the aim of rationality? ... Socrates wasn’t arguing with the citizens of Athens because he wanted to blast their buttholes—ah, actually, he did want to do that—but wasn’t there also a thing about, like, truth? And justice?” The reference to Greek pedagogical pederasty is crude, but it also has a deeper meaning: Wynn shares Socrates’s view that persuasion, desire, and reason are inextricably related.

Socrates knew that anyone who wishes to win minds must also win hearts. He didn’t just earn the intellectual respect of his students; he inspired love, too. His acolytes followed him around the marketplace, hanging on his word, and one of the most moving speeches in the Platonic canon is the description by Alcibiades of his hopeless infatuation with the older philosopher. And of course Plato’s dialogues themselves are, along with being philosophical masterpieces, early examples of fan fiction. In other words, Socrates persuaded by both the logic of argument and the dynamic of fandom. Wynn is beginning to grow a dedicated following of her own: Members of online discussion groups refer to her as “mother” and “the queen,” produce fan art, and post photos of themselves dressed as characters from her videos.

This is not to say that Wynn is Socrates’s second coming, simply that she shares Socrates’s view that philosophy is more an erotic art than a martial one. As she puts it, she’s not trying to destroy the people she addresses, but seduce them. The entire ContraPoints world is designed with this aim in mind. “The visual elements of the videos, the makeup and the costumes … these things have nothing to do with justice and truth but, nonetheless, it really changes the experience of the video,” she told me. In “The West,” Wynn delivers her opening satirical monologue covered in glitter and butterflies, wearing a costume made of giant, transparent wings studded with Christmas lights. The first step in seduction is catching her target’s eye.

Yet for Wynn, the true key to persuasion is to engage her audience on an emotional level. Again, she’s following the Socratic playbook: Plato’s Phaedrus features Socrates at his most flirtatious, trying to persuade a young man who loves listening to speeches to hold the content he consumes to a more critical philosophical standard. In the course of the dialogue, Socrates explains that, to be effective, an orator must know what type of soul his audience has and match his speech to their particular tastes.

Wynn’s determination to do both of these things is what sets her apart from other left-leaning media personalities. Late-night hosts such as John Oliver and Stephen Colbert, for example, are in the business of delivering laughs to a liberal audience by holding up some of the most spectacular examples of conservative ignorance or hypocrisy. But these commentators rarely make much effort to understand or commiserate with those they’re criticizing. Meanwhile, Wynn spends weeks in the online communities of her opponents—whether they’re climate skeptics or trans-exclusionary feminists—trying to understand what they believe and why they believe it. In Socrates’s words, she’s studying the souls of her audience.

One thing she has come across repeatedly is a disdain for the left’s perceived moral superiority. Anti-progressives of all stripes, Wynn told me, show an “intense defensiveness against being told what to do” and a “repulsion in response to moralizing.” Hence, Marie’s resistance isn’t rooted in deeply held opinions about climate science, but in a suspicion that she’s being patronized by smug liberals. Wynn avoids the kinds of things that tend to spur such reactions, such as appeals to victimhood or “feelings,” or even a whiff of self-righteousness.

Matching her speech to the audience’s tastes presents a prickly rhetorical challenge. In an early video, Contra complains: “The problem is this medium. These goddamn savages demand a circus, and I intend to give them one, but behind the curtain, I really just want to have a conversation.” Philosophical conversation requires empathy and good-faith engagement. But the native tongue of political YouTube is ironic antagonism. It’s Wynn’s inimitable way of combining these two ingredients that gives ContraPoints its distinctive mouthfeel.

In the first 90 seconds of “Does the Left Hate Free Speech? (part 1),” Wynn’s persona deploys dripping sarcasm and mocks the prominent YouTube talk-show host Dave Rubin for (literally) crying over liberty. It’s the kind of joyful rancor that gives online polemics their zest. But as soon as viewers have enjoyed the joke, Wynn backs off and acknowledges that plenty of educated and sincere people sympathize with Rubin’s views. Then she extends something akin to an olive branch: “Pull up a seat. Let’s talk.”

This is the subtle difference between Wynn and many of her prominent YouTube counterparts on the right—the ones who summon their opponents to the arena of debate, hungry for victory and for the cheers of their supporters. Contra does her makeup, dons her pearls, and invites her opponents and her viewers into the parlor for cocktails and conversation. The talk isn’t quite a heart-to-heart. Contra’s burns are scorching, her satire precise, and many of her arguments reduce her opponents’ positions to rubble. But somehow, when she does it, the effect is humanizing rather than bullying. She’s flirting, not fighting.