With thick, fake eyelashes, bedazzled gel extension nails, exaggerated lip makeup and flashy jewelry, YouTube star Natalie Wynn opens the first few minutes of one recent video dressed in drag. The irony of this she’s quick to point out.
“Some people say I’m a man dressed as a lady. But, I’m actually a lady who used to be a man dressed as a man dressed as a lady,” Wynn, the transgender, one-woman force behind the “ContraPoints” YouTube channel quips. “What matters more: The way things are, or the way things look?”
Such loaded questions reflect the core of her brand, the captivating, web-based persona she has developed for her more than 750,000 subscribers. On topics ranging from gender and sexuality (“Pronouns,” “Beauty,” “Transtrenders,”) to internet culture and politics (“Incels,” “Are Traps Gay?,” “Why the Alt-Right Is Wrong,”) she often plays the parts of several characters, each with a persuasive, often contradictory, point of view. This requires not just sharp, tactical writing and video editing but also distinct, at times grandiose, costumes complete with their own head-to-toe looks. Whether she’s Marie Antoinette boasting a giant headpiece of tight, stacked blonde curls or a nude creature of the woods adorned only in stick-on butterflies, her transformations never appear sloppy or half-baked, her logic never porous or hollow.
Employing wit, theatrics and academic-level insight, she challenges viewers to abandon their assumptions and lose themselves in this staged, scripted fantasy world, a compelling marriage of reason and humor.
The goal of her YouTube channel, Wynn said, remains the same as when she launched it in her basement about three years ago: To juxtapose intellectually based arguments with over-the-top bravado to debunk misinformation and educate the masses while keeping them entertained — perhaps changing a mind or two along the way. With videos generally reaching audiences of over a million each, she’s considered a leading voice in the transgender community, part celebrity and part viral personality, part scholar and part influencer.
Though Wynn, a self-described socialist, admits she doesn’t necessarily need the pricey props, elaborate dress and spicy innuendo to effectively communicate with audiences, she said the thrill of living out her flamboyant fantasies satisfies the parts of herself she previously repressed.
“There was always this aspiration to this kind of opulence that I had and did not really have the means of achieving,” she said. “There was always an aspiration to be this kind of glam goddess, which is not a real thing; it’s a show, a performance.”
Wynn, whose previous life included stints as a piano teacher, an Uber driver and a paralegal, grew up in Northern Virginia, where she attended James Madison High School and came close to dropping out, she said. A diligent piano player, she earned a spot at Berklee College of Music in Boston.
After college, she pursued a doctorate in philosophy at Northwestern University and realized that despite her knack for deconstructing arguments down to the metaphysical, the field did not fulfill her emotional needs.
Rerouting her life plan, she moved to Baltimore. Now, roots planted, she proudly calls Charm City her home, citing Hampden’s Bluebird Cafe and Bazaar boutique as her favorite spots to frequent.
But she’s not sure how long the East Coast can sustain her. With a growing audience, increased media visibility and a more generous budget funded by crowdsourcing platform Patreon, she often contemplates a move to Los Angeles.
For Wynn, a growing online footprint also entails increased responsibility to bridle her tongue. Recently, she became ensnared in a Twitter feud after expressing discomfort with gender-neutral pronouns (“they,” instead of “he” or “she,” for example). Briefly, she deactivated her account.
As a trans woman who publicly chronicled her transition on the internet, Wynn said she’s no stranger to harassment and vitriol. But when it comes from communities and individuals she considers allies, she said, it hurts all the more.
“There’s people who want me to be representative of trans people, and when I do something they don’t like, it’s like treason," she said. "And those people are so much closer to me, I see them more and I care more what they think. To have to deal with both these things at once, I just shut down a lot of days.”
But unlike her pursuit of a doctoral degree, Wynn said she won’t quit, for her career not only affords her the creative outlet and following she craves as a performer but also enables her to make a tangible difference online, where insults, hatred and threats of violence no longer shock the conscience.
“Natalie if you see this you are my hero,” one YouTuber wrote in the comments section of a recent video. “You’ve helped me accept myself and u understand that I can be polysexual and trans. You’ve validated my existence.”
“You have helped so many people understand trans rights, myself included,” echoed another viewer. “I was a ‘rationalist’ anti-feminist before I found your content and I know there are many others who have a similar story. You have brought so many people to understand and the community at large owes you a great deal of thanks.”
To this end, Wynn said there’s at least some evidence that her approach to the internet, however showy or absurd, is working.
“I have the sense of humor of an edgy teenage a------, so I’m able to relate to people like that,” she said. “I don’t think a lot of people who are talking about, say, transgender issues or racial justice, are really relating to people in that way.”
Wynn’s content allows viewers to reach their own conclusions as characters peel back their layers and defend their points of view. Often, she aims to represent all sides of an argument, an effort she thinks other YouTubers, even other trans YouTubers, avoid.
Her videos also reflect a moment in time, one in which the transgender community finds itself caught in between the dizzying buzzword culture of two political extremes. While some Republicans favor limiting the community’s access to gender-specific bathrooms and the military, members of the political left have attempted to champion trans rights issues ahead of the 2020 elections. But, to Wynn and her predecessors, the politicizing is neither timely nor entirely welcome.
“It’s hard to even remember 15 years ago that the validity of homosexual marriage was debated in exactly the same way that trans people are now debated,” she said. “It’s all the same stuff, and I hope that it leads to long-term, more acceptance and tolerance for trans people, but in the short term, it honestly sucks. Because the increased visibility means increased hostility."
And as the LGBTQ community finds itself accepted by more Americans, according to national polls, Wynn and others like her have seized on the public’s budding interest to explore issues of critical importance to them. In the video “Gender Critical,” she expands upon the reasons behind some “radical feminists’” hostility toward the transgender community; in “The Darkness,” she explains the pervasive conflict between humor and sensitivity; and in “The Apocalypse” she reviews the dangers of climate change and the public’s relative ambivalence to it.
Academics, scholars and media outlets have taken notice of her perspective. Christina Hoff Sommers, a resident scholar at the American Enterprise Institute who specializes in politics and feminism, said Wynn brings humor, imagination and civility into the “often dreary” debates about sex and gender that frequently pit opposing sides against one another.
“She is never strident or didactic — she’s funny and entertaining,” Sommers, a critic of contemporary feminism, said. “You change minds by making people think. If you can make [them] laugh too — you can win their hearts.”
She’s also accepted a request from the U.S. Library of Congress about including her YouTube channel in its LGBTQ+ Studies Web Archive for posterity. Megan Metcalf, the librarian and collection specialist tasked with selecting and preserving the archive, said in an email that Wynn produces “unique and invaluable primary source materials” that document the knowledge and creativity of this generation.
“LGBTQ+ people and communities have not had equal access to mainstream publishing platforms ... [and] have typically been left out of institutions of cultural memory, and therefore, left out of the historical record,” Metcalf said in the email.
Still, Wynn said she frets about the future and aging out of her ability to champion the risqué online. She envisions retiring from YouTube someday in favor of the pen, perhaps to pursue editorial writing or commentary. But for now, she’s focused on promoting the latest video, “Opulence,” which she filmed at the Maryland Institute College of Art with a crew.
It’s a step up from the low-cost microphone and iPhone production work of her past. She doesn’t miss those days. In fact, it’s one of the many elements of her life before the transition that she’d prefer to leave behind.