o call Natalie Wynn a YouTuber seems like a terrible understatement. On a platform awash in makeup tutorials, guys playing video games, horrible comedy and conspiracy theorists, Wynn – whose YouTube channel is called ContraPoints – is someone truly original: a provocateuse, a video essayist and a warrior against the alt-right in ways you would never expect. Her videos are political in nature but feel like theater, involving many costume changes and references to philosophers and academic texts. She can switch from discussing Taylor Swift to Wittgenstein with the snap of a fan. Sharp and funny, she’s a comedian who wields her wit in the service of exposing bigotry and making people examine their own biases. She also happens to be a trans woman, and often talks about trans identity and rights. She’s unafraid of not fitting into anyone’s idea of what she’s supposed to think, and that catches her a fair amount of flak. Millions of people know this already. ContraPoints, which launched in 2016, has more than 1.3 million subscribers. Her videos over the last few years – on cancel culture, on the conservative author Jordan Peterson (whose image she speaks to directly from the bathtub, referring to him as “daddy”) – have attracted tens of millions of views. Her 2018 video about incels, in which she manages to get us to contemplate their pain while still raising an alarm about their unbridled misogyny, generated 4m views alone. All of this has made it possible for her to live on the funding of the more than 13,000 fans who donate to her Patreon account (she doesn’t do ads or endorsements). I traveled to Baltimore on a grey, muggy spring afternoon to visit Wynn at her large, and largely unfurnished, four-storey Victorian townhouse (a rental). The house goes with a certain 19th-century feel projected by Wynn’s arch internet persona – you can imagine her sipping absinthe with Oscar Wilde – but the woman who came down the stairs to greet me looked like a blonde 1970s icon: sort of Marianne Faithful circa 1971. Wynn, 32, is tall, slender and as pale as moonlight. She was wearing light-blue jeans and a sheer, long-sleeved top. Her manner in person is the opposite of the brassy, sassy dame you see in her videos; she’s soft-spoken and doe-like, with big brown eyes. We went and sat in her high-ceilinged kitchen upstairs and talked for three hours while snacking on raspberries and blueberries. Days before I came to see her, the Texas state legislature passed a bill that made providing gender affirming health care to transgender minors “child abuse” – one of many attempts in that state and around the country to prevent transgender kids from transitioning before their 18th birthday. In 2021, 33 states have introduced more than 100 bills aiming to curb the rights of transgender people in general, a record-breaking year for such legislation. These bills come in the context of an increasingly hostile climate for trans Americans, where 28 transgender and gender non-conforming people have been killed this year – nearly all Black and Latina trans women. Advocates for LGBTQ rights say that these bills have contributed to transphobia and violence against the trans community. Wynn seemed troubled by how this new Texas bill was going to affect trans kids and their families. “It’s difficult to talk about this topic because most people don’t know that much about it,” Wynn said in her gentle way. “I think the average person hears ‘transgender medicine and children’, and that doesn’t seem like a good idea because what they’re envisioning is, like, genital reassignment surgery, which is almost never performed on people under 18. “Most of the time, what we’re talking about is puberty blockers,” she said, “which are pretty well-tested drugs that are used to delay the onset of hormonal puberty. Basically, kids who use them end up needing less surgery later. Life is easier for them. A lot of people have this concern, ‘Oh, how could you possibly know when you’re 12 or 13? Why not just wait until they’re adults and let them decide?’ Well, for some kids, they’ve known since they were five, and this is urgent for them. If you have a kid who for years has had gender dysphoria, this is a persistent thing. If you take those kids and you won’t let them transition, it’s torture.” “I think that anyone should be able to imagine what it would be like to go through the wrong puberty,” Wynn added. “If you’re a woman, imagine that your body’s getting hair and your voice is dropping … You’re basically creating refugees of these families who have to go to other states in order to take care of their children.” “It’s very upsetting,” she added. One of the hallmarks of Wynn’s rhetorical style is her ability to get her viewers to see things from another person’s point of view; which in the case of trans children hits close to home, although she says she didn’t know she was trans herself until later in life. “I was not a trans child,” she told me. “I wouldn’t say that I was a girl trapped in a boy’s body. I was able to live as a boy. Being a boy was OK, but being a man wasn’t.” Her journey of self-discovery has been a running theme on her channel, often presented in humorous, self-deprecating ways that seem designed to help the viewer relate to her struggle. One can imagine the dramatic shifts in her own identity may be partly why she balks at cancel culture. She was the subject of a cancellation campaign herself in 2019, when she became the target of a wave of harassment after her video Opulence, which attacks consumer culture and our obsession with wealth, used a voice-over from Buck Angel, a transsexual porn star who had in the past made statements considered offensive by some in the transgender and non-binary communities. “He has a lot of outdated and grumpy opinions about trans topics,” Wynn conceded, “but to me he’s still some kind of legend. “If you don’t fit into the social justice warrior idea of the checklist of opinions that you are allowed to have as a trans person, you might face punishment,” she went on. “One of the things I really don’t like about my own generation is the hyper-moralism of it. It’s like this extreme Spanish inquisition mentality that we have on social media, of trying to detect the signs of heresy and root it out. “I think a part of it also has to do with me having succeeded as a trans woman … I know it’s gauche to be like, ‘Haters and losers are just jealous of me,’ but succeeding as a trans woman, it’s like you went to a low-income high school and then you’re the one who goes to Harvard Law. The other people in the high school are going to have feelings about it. “The whole internet is about jealousy,” she continued. “It creates such animosity between people because it’s all about people envying each other. It’s so unhealthy in every possible way. I’m working on a video about this – envy – which is an interesting topic because of social media, which is all about promoting envy and making people unhappy with what they are and what they have.” She said she’d been reading up on Buddhism in preparation. Wynn was born in Arlington, Virginia, and grew up in a nearby suburb. Her mother is a doctor who practices geriatric medicine; her father a psychology professor. “For the first 20 years of my life,” she said, “I was entirely interested in music.” She attended Boston’s prestigious Berklee College of Music. A shiny grand piano sits in the living room of her Baltimore house. “I still play almost every day,” she said. “Now it’s for pleasure, but when I was younger it was clearly some kind of escape.” “I was OK until I was 14 or 15,” she said, but then she started having some trouble. She was sent to mental health professionals who at various times diagnosed her with depression, bipolar disorder and ADD, among other things, for which she was prescribed Zoloft, Klonopin and other drugs. She now questions those mental health assessments and is no longer taking any psychiatric medications. “One thing I was treated for that I think is nonsense,” she said, “is I was diagnosed with OCD when I was 15. The reason for that was that I was spending too much time on grooming, they decided. Meaning like hairstyling and things. That, to me, is gender enforced through psychotherapy. I strongly disagree with that, because if I had been a girl, I don’t think anyone would have been concerned that I was spending half an hour a day on cosmetics … Gender is very aggressively enforced on teenagers.” After Berklee, she became a philosophy major at Georgetown, where she started exploring her attraction to women’s clothes in a more public way. “I would cross-dress in bars. It was fun, although a lot of alcohol was involved,” she said, smiling wryly. “I would paint my nails and do makeup and stuff. By the time I was in grad school” – at Northwestern, where she pursued a PhD in philosophy – “I was 25. I wasn’t passing as a woman or anything. People still recognized that I was a man.” Wynn recalled a woman in her department who was a “terf”. “She told me that I needed to get psychiatric help because of the makeup and nail polish. I think she was very hostile to any feminine ornamentation, period, and viewed that as the dressings of male oppression forced upon women.” Wynn’s ability to see the other person’s side of things often extends to those who have hurt her as well. “I always sympathize with these people,” she said. The woman at Northwestern “is not a happy person”, she said. “I feel bad for her … I think there’s a lack of understanding about male femininity and what that means in our culture and how it’s treated. Men wearing makeup is not appropriating female culture. There’s no such thing as female culture. Gender is within a culture, and gender mandates categories of existence, I guess, and it forces you into one based on the sex assigned to you at birth.” It’s stunning to see Wynn’s talents at work in her video JK Rowling, posted in January, which has gained nearly 3.5m views. In the video, Wynn – who for most of it is dressed as a witch, a sardonic nod to Rowling’s billion-dollar Harry Potter franchise – takes up the question, much discussed on Twitter, of whether Rowling is transphobic: a question ignited by some of Rowling’s own tweets, as well as an essay she wrote in 2020. Wrapped in this question is also the question of whether Rowling should be cancelled. Wynn’s answers to these questions seems to be yes … and yet, no; she seems less interested in cancelling Rowling – whose books she says she enjoyed as a child – than in prompting her viewers to consider the possibility of their own lurking transphobia. “That essay that [Rowling] wrote,” she said, “honestly reads to me as a cry for help. She talks about her own experience being sexually assaulted and having never spoken about it before, and her own difficulties with gender and bad feelings growing up. All this is associated in her head somehow with trans people. To me, I see trans people as a weird outlet for this pain that she’s harboring and needs to find something else to do with.” And what would she say to those who argue that someone like Rowling should be cancelled for the harm she’s done by spreading her views? “If we can criticize people constructively,” Wynn said, “there’s a chance that these moments could actually educate people and potentially help the person that we’re mad at transform themselves. I try to take a more humanistic perspective when it comes to the topic of bigotry.” Wynn started making videos in 2008, when she was 19. She made videos of herself playing the piano and talking about atheism, a former subject of interest. But it wasn’t until the misogynistic online harassment campaign Gamergate happened, in 2014, that she started to think about using YouTube as a political tool. It was scary to her, because no one seemed to be speaking against the villains of Gamergate. “It felt like a rumbling. And, in retrospect, I see that it was the earth shaking as Trumpism approached. YouTube just exploded with rightwing content. I felt I ought to do something about it, and I also felt I could. I started recognizing I have the skillset to step in.” She developed her style, posting a number of videos before launching ContraPoints in 2016. She had dropped out of grad school by this time and moved to Baltimore for a relationship with a man that didn’t end up lasting. “I went through a period of deluding myself into thinking I was a heterosexual woman,” she said. “It’s easy to fit in that way, I guess. I was figuring it out. There was a period where I was like, no, I’m just a man who likes feminine things. Then there was a period where I identified as gender-queer – non-binary basically. At some point, I realized I want to actually medically transition, and I was like, OK. That’s when I changed my name and started identifying as a trans woman,” in 2017. Last year, she made a video entitled Shame, in which she came out as a lesbian. “How do I put this delicately?” she says in the video. “Your humble hostess is a total les.” “I’m not the same person I was five years ago, or even a year ago,” she told me. “But then,” she asked, “who is?”