The Rise of the Video Essay as Art: ContraPoints

Feb. 16, 2021, 8:29 p.m.

The YouTube of today is a vastly different platform from the YouTube of yesteryear. Once characterized by cheesy, poorly-filmed comedy skits and the dominating presence of Vevo, it was a mecca of low-brow humor and cat videos. YouTube’s audience, however, has matured, and so has its content. 

The video essay is taking over YouTube as a primary form of content on the platform. YouTubers with niche knowledge and impeccable production value are becoming major stars. These YouTubers are smart — they have high level knowledge about topics from critical theory to historical dress — and they perform for the camera in a manner that is entertaining, educational and far-reaching. Many viewers are flocking to YouTube, not just to laugh, but to learn — and the best creators offer both. 

The video essays I will discuss in this column are nothing short of works of art. They often combine musical score, high fashion and makeup alongside performance and narrative, with sturdy cultural critique and analysis that is both complex and easily digestible. And, perhaps most importantly, they are a hoot to watch.


You can’t talk about YouTube video essays without mentioning ContraPoints, also known as Natalie Wynn. She is one of the pioneers of this digital movement toward video essays, and her videos, perhaps best described as “films,” present some of the highest art, critical analysis, skilled performance and humor that the platform has to offer. Wynn delivers all of this surrounded by elaborate sets and beautiful score, while wearing full drag, tipping a 40 oz. to the head and engaging her own hilariously on-the-nose characters through dialogue, a la Plato. If anyone can be described as the intellectual figure of this generation, it’s ContraPoints.

The Rise of the Video Essay as Art: ContraPoints
(Photo: ContraPoints, “Canceling”)

Wynn might be described by some as a “classically trained academic.” She studied piano at Berklee College of Music and received a bachelor’s degree in philosophy from Georgetown. She then attended Northwestern to pursue a Ph.D. in philosophy. 

But this is where Wynn’s career diverged from the traditional academic. She dropped out of the Ph.D. program at Northwestern, saying to Vice News, “The idea of being an academic for the rest of my life became boring to the point of existential despair.”

The Rise of the Video Essay as Art: ContraPoints
(Photo: ContraPoints, “Incels”)

Wynn plays an important role in the contemporary intellectual community — she is no modern liberal. ContraPoints, rather, is a radical leftist. But while many modern left-liberal movements have condemned discourse with “the other side,” ContraPoints has embraced it. She doesn’t shy away from engaging with the arguments of incels, the alt-right, TERFs and public “intellectuals” such as Ben Shapiro and Jordan Peterson (whose visage she hilariously flirts with in a bathtub). 

This is where Wynn’s academic training combined with her high emotional intelligence make her a powerful public presence. She’s been credited with converting many young alt-right leaning men away from dangerous racist, sexist, transphobic rhetoric. If you’ve ever argued with an alt-righter or “Trumpist,” you might be wondering, how the f*** does she do it? 

Wynn herself says, “It’s not just about calling someone out and using logic, because there are emotional and psychological reasons that people hold their political convictions. From a psychological standpoint, you have to empathetically enter a person’s world; not just why do they think what they think, but why do they feel what they feel? Repeat that back to them and you can really gain traction.”

Indeed, her critiques are always based on charitable interpretations of the arguments that she addresses, and her combination of philosophical argumentation and sociology has proved to be powerfully effective. For many, it’s difficult to explain to someone why white supremacy is wrong, they just know that it is. But ContraPoints can do it. Her video on the alt right breaks down both the factual incorrectness and negative ethical value of common, normalized white supremacist arguments. She takes the alt-right’s very own arguments and talking points and breaks them down in a clear, charitable and thorough way that makes her critique nearly impossible to dispute. She puts words to concepts that, for many, have been impossible to describe. And she does so in a way that reaches people on every side of every aisle.

Contra’s content isn’t just devoted to changing the opinions of alt-righters. She also makes video essays that critique and analyze cultural phenomena (such as “cringe,” “beauty,” “cancelling” and “degeneracy”) with the double-edged sword of philosophical breakdown and extreme drag looks. These videos are fun, but so solid in their argumentation that I was able to use “The Darkness” as a source for my philosophy capstone paper; they have true academic utility. Within these films, she discusses each topic as it pertains to gender, sexuality, behavior, personal beliefs and more. She works out meaningful and thorough descriptions for these topics that provide exquisite foundations for her analysis. She, critically, has perfected the fine art of meaningfully differentiating between expedient political rhetoric such as “trans people are born in the wrong bodies” (phrasing which is not philosophically nuanced, nor true to every trans person’s experience, but is critical to the acquisition of rights for trans people) and more complex metaphysical discussion about gender, sex and orientation which many modern academics shy away from. 

The Rise of the Video Essay as Art: ContraPoints
(Photo: ContraPoints, “‘Are Traps Gay?'”)

What puts ContraPoints a step above the rest is her bold, critical and unapologetic nature. She’s not nice. She doesn’t cater to anyone or anything, left or right. She’s not afraid to say, “I am an evangelical transsexual. I don’t want toleration, damn it. I want converts,” and she certainly doesn’t care whether you think she means it or not. She pursues what’s true, what’s expedient and what’s hilarious. And she does it all while dressed as a sexy catgirl. 

The Rise of the Video Essay as Art: ContraPoints
(Photo: ContraPoints, “Justice (Part 1)”)

Natalie Wynn’s work is of the highest art, but don’t just believe me, check it out for yourself. Did I mention she’s funny?

Contact Rachel D’Agui at rdagui ‘at’

Rachel D'Agui is a member of the editorial board and a contributing writer in the Arts & Life section. Contact her at rdagui 'at'

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