The videos often have a classical music score, which tracks, as Wynn went to Berklee College of Music as an undergrad. (She plays piano and, more recently, the harpsichord. Downstairs in her brownstone, a semi-grand piano sits across from a beautifully ornate harpsichord, as though prepared for a round of dueling keyboards.)
She often does costume or even set changes, mid-video. She also has conversations with herself—playing both herself and a skeptical interrogator. She does voices, accents, characters. She interjects video clips and photos, often for comedic purposes. She wears hats (so many hats).
In a world of bare bones podcasts and boring Twitch streamers, Wynn puts on a show. Which is a good thing, because the videos can be up to three hours long. Yes, three hours of just Natalie Wynn talking. (TikTok is not the medium for her. She puts the “long” in long-form video.) But the talking is captivating—funny, erudite, provocative. She’s the coolest philosophy professor you never had.
Wynn grew up in Vienna, VA, with a medical doctor mother and an academic psychologist father (they’ve since divorced). She says her childhood wasn’t all that great.
“I mean, it’s not like I was working in the salt mines or anything,” she says. “But I wasn’t happy—there was lots of psychiatry involved.”
The gender exploration came later. She rues the fact that she didn’t grow up during our current gender revolution—it might’ve helped her figure things out more quickly. But mostly, she says, she was restless, anxious, and a little depressed.
She dropped out of Berklee and eventually landed at Georgetown, where her father worked. “I got a massive tuition benefit because, you know, nepotism,” she cracks. After graduation in 2012, she got a master’s degree in philosophy from Northwestern. The philosophy degree comes through often in her videos, where she routinely quotes Spinoza, Wittgenstein, and Socrates.
After Northwestern, she moved to Baltimore in 2015 because she was dating someone who lived here. It didn’t work out. “Once you switch your long-distance relationship to a short-distance relationship, the whole dynamic changes and it falls apart,” she says.
But she had fallen in love with Baltimore—it’s unpretentiousness, the beauty of its architecture, the history, its “weirdness,” the fact that “it feels like nature might reclaim the city at any moment,” she says. And she has joined the cult of RoFo—“a KFC inside a 7-Eleven,” she marvels. So she decided to stay.
At first, she was doing the gig economy thing. She gave piano lessons. She drove an Uber. She did some copywriting for Overstock.com. (“I remember this anger at having to write five paragraphs on a pillowcase,” she says.) It was around 2014 and something called GamerGate was going on—basically, a misogynistic harassment campaign directed at women who had the temerity to enter the previously male-centric world of gaming. In a way it was a precursor to a lot of the toxic things still happening in our culture—QAnon, the alt-right, doxxing.
That was when Wynn made her first YouTube video, about GamerGate. It didn’t do very well. But she kept making them and started gaining a following.
“I got viewers because I was making responses to bigger creators,” she explains.
She also got better at making the videos—and adopted the melodramatic, rococo style she has now become famous for.