“The first time I used milk in a video was because I thought it looked like semen, and I thought that was funny,” says Natalie Wynn, otherwise known as the American YouTuber, ContraPoints . She's chuckling on the other end of the phone as she dispels this Reddit myth that she uses milk in her videos to reclaim it from the alt-right, which has taken to wielding it as a symbol of white supremacy . “There’s a complex semiotics of milk,” she admits, "but why did I pour milk on my face? Was I thinking about its connection to power or sex? I don’t know; I probably just laughed!”

Until that point, Wynn, who is now 30-years-old, had devoted much of her life to academia. She was born and raised in Virginia but later moved to Illinois, where she studied for a PhD in Philosophy at Northwestern University. “The idea of being an academic for the rest of my life became boring to the point of existential despair,” she recalls half-jokingly—it’s hard to tell: She later describes her PhD as a “guided tour of history’s most boring homosexuals.”

Wynn “tinkered” on YouTube for more than a decade before arriving at this formula. To begin with, she was “a minor participant in YouTube atheism content because that’s what you did as a person with opinions in 2008.” But in 2016, she began ContraPoints: a response to the atmosphere she saw building online. “I noticed a surge of political content around GamerGate in 2014, and it was pretty right-wing—or at least anti-progressive,” she tells me, citing a spectrum of content ranging from the centrist to the straight-up Neo-Nazi. She decided to create her own videos, and these “tinker-toy attempts” at deconstructing social justice issues through a left-wing lens soon caught on. More importantly, they became a creative outlet.

These sorts of elaborate theories aren’t uncommon when it comes to Wynn's work, and they’re evidence of the intense attention people pay to her videos. Combining humor, drag, and philosophy, she is one of the most incisive and compelling video essayists on YouTube. Her latest video 'Gender Critical' (a term radical feminists have taken to using in reaction to being called TERFs [trans-exclusionary radical feminists]) racked up almost half a million views in a day. From the context of comedy to transphobic memes , ContraPoints is doing the seemingly impossible: making nuanced and controversial political debates both sexy and engaging.

Race was a key focus of ContraPoints’ earliest videos. In pursuit of a relationship, Wynn moved to Baltimore after dropping out of college. There she found a city in the midst of “an uprising” after the murder of Freddie Gray—a young, wrongfully-arrested black man who died due to injury in police custody. No officers were charged. Soon, she started seeing “violently, viciously racist” online comments that were being ignored, a fact that frustrated her. “I thought that if people are leaving these comments, they're thinking these thoughts all the time," she says. "People told me I was crazy, but then the 2016 US election confirmed that people were voting the same way they were leaving YouTube comments.”

She describes being fundamentally miserable, juggling numerous jobs to “fund failed artistic attempts.” That’s when she noticed that pseudo-intellectualism was beginning to creep into right-wing discourse, propelled largely by the likes of “phony philosophers like Stefan Molyneux,” whose popularity proved there was an audience for philosophical takes on political issues. “They were selling it to people who craved this kind of commentary, but were just getting into a horrible version of it,” she says. ContraPoints was conceived to balance the political playing field by dissecting issues through a left-wing lens. “That’s one thing I learned in my philosophy training,” she adds, “if you’re writing a paper on Aristotle, you have to first show that you understand him. Then you can make your counterargument.”

Online radicalization became another key theme in ContraPoints videos. Her essays on ‘decrypting the alt-right’ and incels garnered millions of views, as did her thorough debunking of prominent alt-right commentators like Ben Shapiro and Jordan Peterson.

“They take these tired, old-fashioned racist reactions and present them as an edgy new thing, and it’s powerful rhetoric,” she says. “They understand how to make these ideas sexy and dress them up for public consumption; what drives me crazy is that the left doesn’t seem to have that intuition on how to publicly present a thought.” The fatal impact of this alt-right rhetoric was laid bare by the recent Christchurch mosque massacres. “People still think these are just memes, just jokes,” she says, her voice heavy with frustration. In a tweet posted in the wake of the tragedy, she wrote: “No satisfaction now, just anger. No one listened.”

Wynn acknowledges that to de-radicalize someone you have to engage with their ideas, but this method isn’t exactly popular. “The only way I was able to make these videos was to have conversations with centrists, or with people that were going in an alt-right direction,” she explains, “I was doing what you’re literally not supposed to do, which is to talk to them.”