Natalie Wynn

Natalie Wynn (born October 21, 1988) is an American left-wing YouTuber, political commentator, and cultural critic. She is best known for her YouTube channel, ContraPoints, where she creates video essays exploring topics such as politics, gender, ethics, race, and philosophy.

Her videos often provide counterarguments to right-wing extremists and classical liberals. They comment on modern social issues such as class inequality, transgender rights (as well as LGBTQ rights more broadly), cancel culture, and modern internet culture. Her videos make use of set design, costumes, and characters.

Wynn 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 Vienna, Virginia. Her father is a psychology professor, and her mother is a doctor.

After studying piano at Berklee College of Music, Wynn attended Georgetown University, where she studied philosophy. She then enrolled at Northwestern University to pursue a PhD in philosophy, where she also served 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"). She 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. She eventually decided 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 not only to explain left-wing ideas but also to criticize typical conservative, classical liberal, alt-right, and fascist talking points. 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 2018 interview for The Verge, journalist Katherine Cross notes a difference between Wynn in person and how she presents herself on YouTube. Cross explains 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."

Wynn provided voice acting for the 2022 Netflix show Bee and PuppyCat.

Reception

Writing for Vice, Jake Hall called Wynn "one of the most incisive and compelling video essayists on YouTube."

The Southern Poverty Law Center has cited her analysis of right-wing use of memes and coded symbols in an article explaining the right-wing use of the OK sign. In The Nation, journalist Liza Featherstone 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. ContraPoints won Best Commentary at the 10th Annual Streamy Awards.

Pronouns and transmedicalism controversies In September 2019, Wynn described her feelings on Twitter 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." whose views on transgender and non-binary people have attracted criticism, including by some who see Angel's opinions as being transmedicalist. 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, Wynn 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." In 2020, in a video titled "Shame," she came out as a lesbian. She endorsed Bernie Sanders in the 2020 Democratic presidential primaries and supports Alexandria Ocasio-Cortez.

, Wynn resides in Baltimore, Maryland. 2020 Streamy Awards

2021 Streamy Awards

2022 Peabody Awards