ContraPoints
Her videos often provide counterargument to right-wing extremists and classical liberals. They comment on modern social issues such as class inequality, LGBTQ rights (particularly transgender rights), cancel culture, and modern internet culture. Her videos make use of set design, costumes and characters. Wynn has won a Streamy Award for "Commentary" in 2020, and was nominated in the same category at the 2021 Streamy Awards. In 2022, she became an honoree of a Peabody Award.
Early life
Wynn was born on October 21, 1988, in Arlington, Virginia, and raised in the same state. Her father is a psychology professor and her mother is a doctor. After studying piano at Berklee College of Music, she attended Georgetown University and studied philosophy, then enrolled at Northwestern University to pursue a PhD in philosophy, also serving as an instructor. She left Northwestern with a master's degree (subsequently stating, "The idea of being an academic for the rest of my life became boring to the point of existential despair"), and moved to Baltimore, Maryland for a relationship, which ended up failing. After quitting her PhD program, Wynn taught piano, and worked as a paralegal, Uber driver, and copywriter, eventually deciding to begin making video responses to the alt-right and Gamergate on YouTube.
YouTube career
Wynn started publishing YouTube videos in 2008, initially focusing on criticism of religion and her position as an atheist and a skeptic. In 2016, she began the ContraPoints channel in reaction to the Gamergate controversy and the increasing prevalence of right-wing YouTubers, shifting her content to countering their arguments. Early ContraPoints videos also covered subjects such as race, racism, and online radicalization.
In her videos, Wynn utilizes philosophy and personal anecdotes to not only explain left-wing ideas, but to also criticize common conservative, classical liberal, alt-right, and fascist talking points. Wynn's videos are said to often have a combative but humorous tone, containing dark and surreal humor, sarcasm, and sexual themes. She often illustrates concepts by playing different characters who debate one another. The videos have been noted for her production choices such as dramatic lighting and elaborate costumes. She borrows some aesthetic cues from drag performance.
In a Wynn 2018 interview for The Verge, author and Information Science student Katherine Cross notes a difference between Wynn in-person and how she presents herself on YouTube, explaining that the channel projects a "blithe, aloof, decadent and disdainful" image, whereas Wynn, personally, "can be earnest—and she cares deeply, almost too much," with Wynn concurring: "Contra has BDE. I do not."
The video channel is financed through the crowdfunding platform Patreon, in which, As of March 2024, it has about 32,500 supporters.
In February 2020, Wynn set all her videos from before August 2017, the time when she began her gender transition, to private, stating that they "no longer represent the person I've become". She posted transcripts of older videos on her website.
Reception
Jake Hall, writing for Vice, called Wynn "one of the most incisive and compelling video essayists on YouTube". New York magazine states, "ContraPoints is very good. Regardless of the viewer's interest or lack thereof in internet culture wars, YouTube Nazis, or any of the other wide-ranging subjects covered in its videos, they're funny, bizarre, erudite, and compelling." Nathan J. Robinson of Current Affairs calls ContraPoints a "one-woman blitzkrieg against the YouTube right."
Media often describe the channel's content as suited to a millennial audience, due to its style and attention to online culture.
Her analysis of right-wing use of memes and coded symbols has been cited by the Southern Poverty Law Center in an article explaining the right-wing use of the OK sign. Journalist Liza Featherstone, in The Nation, recommends the channel, saying that Wynn does a "fabulous job" acknowledging her opponents' valid points while debunking weak arguments and revealing the influence of a sometimes unacknowledged far-right political agenda.
In November 2018, after a ContraPoints video about incels reached over one million views, The New Yorker carried a report on the channel, describing Wynn as "one of the few Internet demi-celebrities who is as clever as she thinks she is, and one of the few leftists anywhere who can be nuanced without being boring." The Verge has called Wynn's "confident and indulgent" persona in ContraPoints as "decadent" in "the mold of Oscar Wilde by way of Weird Twitter," commenting on her postmodern rococo set design and the "bewildering" variety of characters she deploys.
The Atlantic praised the channel's sets, lighting, and music, opining that "the most spectacular attraction [...] is Wynn herself." Polygon named her video on incels one of the 10 best video essays of the year 2018. In May 2019, she topped the Dazed 100 list, which ranks people who "dared to give culture a shot in the arm." ContraPoints won Best Commentary at the 10th Annual Streamy Awards.
Personal life
Wynn is a transgender woman, a matter prominently featured in her videos. She began her gender transition in 2017. She had previously identified as genderqueer. She is a feminist and has called herself a democratic socialist and social democrat. She endorsed Bernie Sanders in the 2020 Democratic presidential primaries and supports Alexandria Ocasio-Cortez. As of 2017, she resides in Baltimore, Maryland.
In 2020, in a video titled "Shame," she came out as a lesbian.
Pronouns and transmedicalism controversies
In September 2019, Wynn described on Twitter feelings of awkwardness when asked in some contexts to describe her preferred gender pronouns. The tweets were criticized as dismissive of non-binary people who use pronouns other than "he/him" and "she/her".
Linguistics professor Lal Zimman said about pronoun introductions, "Wynn is absolutely right that people engage with that practice in ways that can be somewhat problematic". Following constant negative harassment, Wynn deactivated her Twitter account for a week, then posted an apology. Shortly after, Wynn's video "Opulence" featured a quote from John Waters read by transsexual pornographic actor Buck Angel, whose views on transgender and non-binary people have attracted criticism, including by some who see Angel's views as being transmedicalist. Wynn was criticized for using Angel in the video.
At the time, Wynn and other YouTubers associated with her channel were widely harassed online.
Wynn's January 2020 video "Canceling" addressed both criticism of her and harassment, and the broader context of cancel culture. Her stance was praised by Robby Soave of Reason. In a Guardian interview on her January 2021 video "J.K. Rowling", in which she addressed cancel culture in the context of trans-exclusionary radical feminists, she stated she is "less interested in cancelling Rowling – whose books [...] she enjoyed as a child – than in prompting her [Wynn's] viewers to consider the possibility of their own lurking transphobia," adding that she tries to "take a more humanistic perspective when it comes to the topic of bigotry."
Awards
| Year | Ceremony | Award | Outcome |
|---|---|---|---|
| 2020 | Streamy Awards | Best Commentary | Won |
| 2021 | Streamy Awards | Best Commentary | Nominated |
| 2022 | Peabody Awards | Interactive & Immersive | Won |