Natalie Wynn is the smart person's YouTube creator. Her ContraPoints channel, created in 2016, features Wynn delivering searing criticism and engaging all matter of dark subjects — her most popular video to date is about incels, but always with a deep sense of empathy and humor (despite eviscerating the absurdity of their stance and their violent misogyny, Wynn manages to find common ground and even sympathy for the incels). Using philosophy, costume, sight gags, drag and a heaping amount of humor, Wynn is the lecturer we need. — Claire Valentine

What's the biggest misconception about you?

That I'm a bookish intellectual. I'm not. Ok, I spent most of my 20s with my face in a book, but I want to live now. I rarely read more than is necessary for video research, and I keep it light.

What was the last text you sent?

I texted Jaymes Mansfield about the aesthetics of classic iPods.

What's something no one knows about you but you wish people did?

In person I'm very shy and very non-confrontational. I'll do anything to avoid an argument.

What's something you wish no one knew about you but everyone does?

I used to be a man.

What was the last song you listened to?

Kygo's remix of Whitney Houston's cover of "Higher Love" by Steve Winwood.

What's an interview question you never want to be asked again?

"So tell me how you got started on YouTube!"

If you weren't doing this, what would you be doing for a career?

Possibly writing ad copy for Mattress Warehouse, or books about German philosophers. Who knows how low I might have sunk by now.

What's your most disgusting habit?

Sugarless energy drinks, by the crate.

What's the craziest thing you've done in 2019?

I had five major cosmetic operations on my face, all at the same time: brow contouring, brow lift, rhinoplasty, mandible contouring, and trachea shave. It was a terrifying and difficult life event all around, but you should see the way my face looks photographed in profile now. Instagram is loving it.

What's the most stressful thing about being you?

I produce content about complex social issues, and my audience expects me to be thorough, nuanced, well-read, persuasive to outsiders, and deferential to insiders while somehow at the same time being irreverently funny. I'm very stressed right now.

When you want to get attention, what do you do?

I down a couple glasses of rosé and tweet something regrettable.

Do you Google yourself?

God no. There are much more frequently updated places I can go to read about myself.

Photographer: Sean Scheidt
Hair: Ericka Cherrie
Makeup:
Perryn Morris

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