Her earlier videos suggest a vulnerability while she navigated toward a moment of change. The whole process of transitioning is so difficult and awkward that I don’t watch my videos. I feel trapped sometimes by this old self I have represented online. “How do I handle the fact that I have two different gender identities that are immortalized on the internet? It’s what makes this channel so bizarre. “It’s the big question mark in my life,” says Wynn, whose most recent video explores gender dysphoria, identity and beauty. Her videos are as transparent as they are clever, tracking not only the evolution of Wynn’s ideas and production aesthetic but of her insecurities and transformation from a young man in a flannel shirt to a decked-out philosophical diva with hormone induced breasts and feminization surgery that reshaped her jawline and removed her Adam’s apple. Wynn’s mission mirrors our technological, gender-restless, self-revealing culture. “I am an evangelical transsexual,” she slyly jokes in one video. She creates conversations between opposing characters that, depending on your politics and preferences, irritate or seduce, as if one had wandered into a stylized art-house dream (or nightmare) with Socrates, Freddie Mercury and Virginia Woolf as hosts. Costumes are drawn from dress racks, boxes of hats, rows of wigs, handbags and wraps. She shoots her videos in a basement studio crammed with a piano, French-style divan, print wall paper and photographs of muscled men and Chairman Mao. Wynn is of this age, but Twitter cannot contain her, and besides, she says, it’s mean and vacuous. “But the deeper conversation is: What does America look like? Who has power in this country and who doesn’t? What will this country look like in 2050? How much power will women have? How much room will we have for LGBT sexual minorities? These are the big questions underlying what politics is about now.” “What’s happening online is like a canary in a coal mine telling you something’s happening before it happens on a bigger stage,” Wynn says. A right-winger called her “an evil lunatic, a bizarrely popular communist, loser, pseudo-intellectual slug.” One critic, commenting on her wardrobe and makeup, said she was “a bad character from a Tim Burton movie.” Her skewering of all political persuasions has earned her online venom. She says anyone perusing video gamer sites or right-wing YouTube channels in 2016 could have predicted Donald Trump’s election. Wynn skims the dark corners of the internet to gauge the fringe thinking of both left and right. Natalie Wynn/ContraPoints, from one of her videos
The key, especially on YouTube, is to masquerade message as entertainment, which Wynn did recently when she featured a $2,000 gold-flecked pizza to highlight the egregiousness of wealth. YouTube and other channels, not to mention Twitter and legions of chat rooms, are a Darwinian cyberspace where political and ideological battles swirl in countless storms. Her videos are a testament to how the nation’s divides play out across the web. Or as she puts it, “men who have found an identity for not getting laid” and harbor a “searing resentment” of women.
She has criticized the euphemisms and coded hate speech of the alt-right and the moral failings of capitalism, describing the latter as a “repulsive juxtaposition of scarcity and abundance.” In a 35-minute video, which drew nearly 2 million views, Wynn explored the internet subculture of “incels,” young, mostly white men who can’t find romantic relationships. She is that rare presence in our clamorous times: an internet voice resonant not with rage but with satire, humor, nuance and an inviting if at times sardonic sense of persuasion. A public intellectual with a flair for costumes and camp, Wynn, who in videos has dressed as a eunuch and a crypto-fascist, is a progressive liberal who can flay her enemies even as she seeks to understand their beliefs. Wynn is known by her internet alias, ContraPoints. Recording in a row-house studio on a working-class street, Natalie Wynn, a trans woman with defiant opinions and platinum wigs, has emerged as a popular YouTube provocateur, taking on right-wing extremists, radical feminists, climate-change deniers and notions of identity in our seething, selfie-obsessed, meme-driven age.