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 issues that are routinely forgotten or swept under the rug. An intellectual here is the outsider, amateur, disturber of the status quo, but Wynn is more than that. Furthermore, performativity becomes a considerable aspect when we try to analyse the impact of any public intellectual as Wynn performs her life on multiple levels- through rhetoric strategies, literary devices, and public performances. Traditionally, women are thought to be less interested in being visible, less intelligent, less genius than men who are also public intellectuals. Wynn being the representative of BreadTube as a transwoman, shatters these strict norms.

The works that feature the themes of gender, sexuality, transmedicalism, trans women’s sex lives, trans identity, and its social impact are Shame, Gender Critical, J.K. Rowling, Autogynephilia, Incels, Are Traps Gay?, Transtrsnders, and Pronouns. Her work critiques transphobia, transmisogyny, misogyny, and gender roles. In the work Men, she also unpacks the Men’s Rights Movement, fairly evaluating their concerns and calling for a positive men’s rights movement. In Beauty, she discusses the details of her cosmetic surgery and experience and then the dominant, complicated relationship between feminine beauty standards, saying, “beauty is power, that beauty is political.” She addresses the systems of domination and how specific physical markers for women are valued more. There is a relation of these markers to privilege, access, and capitalism.

Wynn’s discussion on gender and sexuality also briefly discusses the language and vocabulary, which falls under the purview of Feminist Science Studies. She discusses how Science has constructed our bodies supplemented by the ideas of racism and eugenics. In Gender Critical (a term used by TERFs), she emphasises Germaine Greer referring to transwomen as ‘it,’ asking viewers if a feminist scholar uses ‘it,’ then what would a man be on the steps of a man liquor store would call a transwoman. While doing so, she also parodies popular shows like having The Freedom Report segment, which mocks The Rubin Report.

Wynn’s work represents trans embodiment by a trans woman composer. She has been critical of TERFs (authoring an extended, engaging, informative essay about J.K. Rowling, bigotry and transphobia), cultural appropriation, pick-up artists, and pop feminism. During her discussion on Ben Shaprio’s claims that pronouns are biological inherently, she showed how the discussion of biology during pronouns shows the authoritative power of Science. Shapiro frames a matter of language using biology, and since one cannot argue with chromosomes or genetics, the discussion around the rights of trans people are fixated upon biology. We do need intellectuals, but they cannot reach many people like musicians or YouTubers do. She also promotes using ‘Trans Liberation Now!’ instead of ‘Trans women are women’ as the former is about rights while the latter is fixated on biology debate and omits transmen and non-binary trans folks.

Representation and ‘Cancel Culture’

The idea of representation is crucial as Wynn is the most famous representative for left-wing transgender creators on YouTube. In addition, by being able to pass as a woman, she embodied an inspirational figure and envied one, which she discusses in her latest video, Envy. She thought-provokingly highlights how oppression, marginalisation, and envy are linked to each other intrinsically. The platforming also makes some audiences doubt whether she is an ally or a celebrity, pointing to the lack of trans presence in media.

Even representation from the LGBTQIA+ community predominantly consists of rich, white, non-disabled, privileged gay men. In general, YouTube does not have a lot of traditional gatekeeping, which works in favour of trans people as no one wants to give them a platform. Furthermore, the traditional gatekeeping that existed in politics and commentary is also gone. This means that anyone with enough confidence, charisma, and a camera can be a political commentator, suitable for LGBTQIA+ people and transgender people.

This also brings in the notion of parasocial relationships that hugely impact her work. The term ‘parasocial relationship’ is used to describe the feelings of affection and sustained connection individuals develop for people they have never met, like celebrities. When Wynn shares her personal experiences, her audience becomes emotionally invested in her, increasing the risk of them being disappointed and feeling a sense of betrayal if Wynn ever does anything they feel as morally reprehensible. Wynn says that she is being treated as a moral brand of community, and the audience does not consider that as a collective; they have terrifying power, which brings us to the idea of ‘cancel culture.’

Cancelling highlights how minorities are much more affected by the threats of their audience abandoning them, adding to the minority stress. Cancelling highlighted the inability to take criticism constructively on social media, again pointing towards binary thinking. There is binary thinking of people as either good or bad, but also hyper-morality, followed by vigilante justice. Cancelling stands apart from the rest of her work without any elaborate set design, characters, or make-up. She gives the instance of cancelling of James Charles, who identifies as a homosexual, where homophobia directed against him resulted in him being given labels of racist, a sexual predator, and a transphobe who at the time of the cancelling was a teenager. With regards to her controversy with Buck Angels, cancelling would seem to follow the logic as detailed below,

Natalie worked with Buck Angel → I do not like Buck Angel because they are a TERF → Natalie works with TERFs → Natalie must be a TERF → She must be de-platformed

In her XOXO Festival video, she also discusses how associations are so quickly marked based upon one photograph. When Twitter cancelled Wynn, her friends, most of whom are also queer and transgender people, were also doxed, insulted and harassed. Wynn rightfully calls ‘cancel culture’ the guillotine of the 21st century – “the bringer of justice and people's avenger but also a sadistic entertainment spectacle.” Even intending to make the world a less ignorant place, there are elements of toxicity that collaborate with patriarchy to double down on women and gender minorities, leading to disproportionate instances of bullying, harassment, doxing, defamation, and double standards against women and gender minorities. Instead, she promotes a cancel culture for constructive criticism and consulting facts, leaving space for growth and improvement.

Accessibility on the Internet

Wynn is what Habermas would call an avant-gardist instinct of the public sphere. Habermas, a normative theorist of the public sphere, identifies the citizen as a private one, engaging with matters of general interest that lead to the formation of a public sphere. Habermas conceptualised the internet as a public sphere, shifting towards the idealised participatory model of the public sphere.

Habermas also tweeted, “It is true that the internet has reactivated the grass-roots of an egalitarian public sphere of writers and readers.” While discussing the structural transformation of the public sphere, Habermas emphasises free speech and freedom of space to have a space to hold public opinions, citing the public sphere as a fundamental feature of democracy. In their book The Permanent Campaign: New Media, New Politics, the authors argue, due to lesser central nodes, gatekeepers, and agenda setters, the internet has become more accessible. Nevertheless, features like images, solitary nature, and speed polarise and limit rational discussion.

However, the normative model put forward by Habermas does not guarantee the participation of women and other minorities. The public debate on the internet advantages established actors due to gatekeeping through technical aspects. This seems to be absent to an extent from BreadTube, where trans and queer creators have found a space. The video essay format separates academia from YouTube and provides a more accessible space to engage with political discussions. Further, there is also a sense of community where creators have been there for each other during hard times. Wynn studied Philosophy, and now she explains these complex ideas in a simplified, engaging, fun manner.

However, despite wide accessibility, the media has failed to cover Wynn’s work on trans issues. It sees her as a rehabilitation centre for de-radicalising white men. While creators like Wynn provide entry points, we need to learn on our own and listen to the people speaking. Through her lived experiences and social location, Wynn provides a much-needed queer, radical, inclusive, and feminist perspective. She introspectively asks the viewer why they believe in certain things. It also becomes crucial to look at Wynn’s work at a time when 33 states in the U.S.U.S. have introduced more than 100 bills to curb the rights of trans people. It is a year where 28 trans and gender non-conforming people have been killed, primarily black and Latina transwomen.

Ultimately, Wynn’s style of persuasion is intelligent and nuanced but engaging, relatable, and entertaining. What makes her unique is her bodily presence, sympathetic and critical address of systems of dominations, call for co-authorship in comments, and conversations about bodies, embodiment, gender, and sexuality. However, Wynn is also a part of the predominantly ‘white’ Left Tube. Kat Blaque, a black trans-YouTuber, has also criticised prominent LeftTubers like Wynn for not addressing white nationalism through their work.


By Rajeev Anand Kushwah (Columnist)

Rajeev is a Queer Bahujan Gender Studies Scholars pursuing M.A. in Women's Studies at TISS, Mumbai. He is a writer at Feminism in India, Gaysi, and The Reclamation Project. He is also an overthinker, a self-proclaimed chef, a pop-culture enthusiast and a poet/writer. His research interests include queer experiences, feminist ethics of care, and pop culture.

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