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Natalie Wynn’s Contrapoints: Humor, Drag, and Philosophy


In Picture: Natalie Wynn

Credits: Dazed

The article reviews the work of trans YouTuber Natalie Wynn (who runs the channel Contrapoints) as a public intellectual of gender, sexuality, and trans experiences; a representative of Left-wing Youtube who discusses the aesthetics and optics of politics; a misunderstood de-radicalising agent on YouTube; and a figurehead well-versed in the nuances of cancel culture. It addresses the complex role of Wynn as a representative of the trans/queer community thriving in the time of attention economy and celebrity culture. Lastly, it also decodes Wynn’s performance of ‘contrapoints realness,’ using drag and theatrics to explain philosophy in a simplified manner.

Breadtube - The Leftwing YouTube

In her video, The Aesthetic, Natalie Wynn asks her viewers,

“What matters more, the way things are, or the way things look?”

The question defines her work in aesthetics, politics, and optics which form a large part of how video essayists work through YouTube. Wynn is a part of BreadTube– a section of video creators who focus predominantly on left-wing perspectives and progressive, queer feminist notions. Natalie Wynn has been described ‘the Oscar Wilde of the internet,’ ‘the transgender-populist fighting fascists with face glitter,’ and ‘a stylish socialist trying to save YouTube from alt-right domination.’ She runs the channel Contrapoints (an abbreviation for 'controversial points'), a mix of humour, drag, and philosophy, supplemented by iconic characters, distinct style with campy lighting, make-up, and wig styling. She has been a part of Youtube's Atheism for a long time now. However, after Gamergate, she started using YouTube as a political tool to promote progressive ideas against the hatred that was becoming common, specifically against S.J.W.s– Social Justice Warriors, a term used to target feminists or movements advocating for social justice inclusive of Black Lives Matter, LGBTQIA+, Muslims, and Immigrants.

Aesthetics and Performance

“Reason is a very powerful aesthetic, if you are a man.”

  • The Aesthetic

Contrapoints lies at the intersection of performance, political activism, and personal confessions. Through drag, Wynn performs Contrapoints realness, embodying a particular type of academic aesthetic. Her early videos also featured sexual innuendo, over the top characters, and self-deprecating humour, primarily driven by the mode of ‘Socratic Dialogue’ in which philosophy has been conceptualised initially. There is also the notion of a Heteronym– the literary tradition of inventing characters who display different traits of the writer’s identity and unique styles. Wynn defines political reality through drag and amazingly detailed and colourful set designs.

The Aesthetic presents a debate between two transwomen where Justine says, “Politics is Aesthetics.” Justine is described as a feminine, passing transwoman focused on the aesthetics (read: politics) of passing and assimilation. The Aesthetic primarily revolves around identity, desire, and womanhood, asking the questions– what does it mean to pass or represent? On the other hand, Tabby is portrayed as a caricature of how people see leftists– a communist, non-passing trans cat girl who wants to smash TERFs (Trans Exclusionary Radical Feminists). Viewers might identify more with Justine due to her appearance and aesthetic, while Tabby has progressive politics albeit in violent ways– reflecting how Antifa is perceived. Tabby notably says, “People on the left are never gonna be “cool,” because anger and emotion are rational responses to injustice.” Although Wynn received flak for seemingly supporting Justine, she is not wrong and says that anger and emotion can also have aesthetic appeal.

Wynn also debunks alt-right politics and notions while discussing how reason, genius, and intellect have been male-coded as concepts. While doing so, she analyses right-wing culture’s appropriation of signs and memes like the ‘OK’ sign of Pepe the frog meme. While it seems ridiculous, the optics and the politics conveyed through these cultural acts significantly impact the proliferation of anti-progressive ideas. Dubbing this as an aesthetic century, Wynn referred to America as a circus where the President is a reality T.V. star. In terms of her work, anti-capitalist sentiments are a more prominent theme. She does not do endorsements or advertisements but does make jokes on her own complacency with capitalism. In Beauty, she says, “I am contributing to corporations out of the goodness of my heart.” There is a more considered analysis of culture through decoding concepts like cringe, beauty, and envy.

On humour, Wynn wishes to emote some laughter out of the things leftist discourses discuss (trauma, oppression, etc.) as it is so grim. One of the funniest aspects was when Wynn used milk in her videos because she found it funny. However, the audience on Reddit thought it represents semen, also white and a marker of white supremacy, making its usage by Wynn an act of reclamation of the symbol. She also uses paper cutouts of Jordan Peterson or Ben Shapiro in her videos, calling the former Daddy. There is also the idea of rewatchability present within her content, highlighting the rise of video essays as informative articles. However, she has been criticised for not addressing cultural differences, which her later work has improved upon.

De-radicalisation or Re-radicalisation?

“Fascism is the aestheticism of politics and the aestheticism of militarism. And Communism responds by the politicisation of art.”

Wynn has mentioned that through her work she wants the viewers to question why they believe the things they believe in the first place. She understands that people believe in things for emotional and psychological reasons, and calling them out through logic will not work. Wynn’s videos also involve people who used to be transphobic before their horizons broadened and minds changed by consuming her content. Caleb Cain started his channel by discussing his story of Descent into the Alt-Right. However, this runs the risk of re-radicalisation as people go from far-right to far-left and not just complacent centrism.

The idea of debating politics also refers to the nature of politics as always being antagonistic and tribalistic. However, social media puts us in isolated information bubbles. We do not just disagree on politics. We disagree on reality in very fundamental ways. A significant part of her work has been theorising upon how marginalisation and oppression works. Wynn’s ‘double bind,’ the concept theorised by the seminal feminist scholar Marilyn Frye is the choice to distance herself from rigid adherence to external feminine beauty norms and risk violence or buy into the norms and give in to the dominant systems that dictate them. Wynn is her most honest, reflective, and personal about her relationship to the norms, and such introspection is followed by the audience in the comment section.

A Public Intellectual of Gender and Sexuality

As Wynn’s channel is about sex, drugs, and social justice, it is vehemently against the traditional YouTube content about sports, music, and comedy. Wynn’s channel is also very personal as it covers her journey of transition, making her a female public intellectual dealing with self-representation in an attention economy. The generation of interpersonal, communal reflections on complex issues around gender and sexuality may give rise to changing beliefs, highlighting its importance in expanding rights around gender and sexuality. She also addresses systems of dominations (heteropatriarchy and cisnormativity) through accepting, rejecting, and subverting language used to oppress and decompose trans bodies and embodiments.

Edward Said’s Representations of the Intellectual (1996) defines the public intellectual as someone who has “a faculty for representing, embodying, articulating a message, a view, an attitude, philosophy or opinion to, as well as for, a public; [She] confronts orthodoxy and dogma, representing people and