Natalie Wynn (born October 21, 1988)[1] is an American YouTuber whose videos explore topics such as politics, gender, race, and philosophy on her YouTube channel ContraPoints. The channel is seen to counter right-wing political argumentation and has been considered influential in the left-wing YouTube video essay sub-genre. Her videos are noted for their use of intricately designed sets and costumes and for her ironic humor.

ContraPoints (cropped).jpg
Personal information
Born (1988-10-21) October 21, 1988 (age 31)
EducationGeorgetown University Northwestern University
ResidenceBaltimore, Maryland, U.S.
OccupationYouTube personality
YouTube information
Years active2008–present
Total views46.4 million
YouTube Silver Play Button 2.svg100,000 subscribers 2018
Updated January 21, 2020

Early lifeEdit

Wynn was born on October 21, 1988, in Arlington, Virginia,[1] and raised in the same state.[2] Wynn's parents are a psychology professor and a doctor.[3] She attended Georgetown University in Washington, D.C., and studied philosophy, then enrolled at Northwestern University in Illinois to pursue a PhD in philosophy, also serving as an instructor.[2][4][5][3] Wynn left Northwestern, saying it had become "boring to the point of existential despair",[2] and moved to Baltimore, Maryland.[2]

Wynn has written fiction, taught piano, and worked as a paralegal and copywriter.[6]

YouTube careerEdit

Wynn started publishing YouTube videos in 2008, initially regarding religion and atheism. 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.[2][4][7][8] Early ContraPoints videos also covered subjects such as race, racism, and online radicalisation.[2] In her videos, Wynn uses philosophy, sociology, and personal experience to explain left-wing ideas and to criticize common conservative, classical liberal, alt-right and fascist talking points.[4][9][10]

Wynn's videos often have a combative but humorous tone, containing dark and surreal humor, sarcasm and sexual themes.[4] Wynn often illustrates concepts by playing different characters who engage in debate.[11] The videos have been noted for showcasing Wynn's production choices such as complicated lighting, elaborate costumes, and aesthetics.[12] In a 2018 interview for The Verge, Katherine Cross notes a significant difference between Wynn and how she presents on YouTube, explaining that the YouTube channel portrays an image of being "blithe, aloof, decadent and disdainful", while personally Wynn "can be earnest—and she cares deeply, almost too much."[13]

The video channel is financed through the crowdfunding platform Patreon, where ContraPoints is among the top 20 creators on the site.[14]


Wynn's videos have been praised for their clarity, nuance, and attention-grabbing sense of humor.[2][11] Jake Hall, writing for Vice, called Wynn "one of the most incisive and compelling video essayists on YouTube".[2] In an article contrasting her personal sincerity and her ironic sense of humor, The Verge describes her as the "Oscar Wilde of YouTube."[13] 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."[4] Nathan Robinson of Current Affairs calls ContraPoints a "one-woman blitzkrieg against the YouTube right," describing her videos as "unlike anything I've ever seen ... She shows how debate should be done: not by giving an inch to poisonous ideas, but by bringing superior smarts, funnier jokes, and more elegant costumes to the fight."[11]

Media often describe the channel's content as uniquely suited to a millennial audience, due to its humorous style and its direct attention to online culture.[11][15][12] Wynn's analysis of fascists' 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.[10] Journalist Liza Featherstone recommends the channel as well, 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.[16]

In November 2018, after a ContraPoints video about incels reached over one million views, The New Yorker released a profile of 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."[17] The Atlantic praised Wynn's use of "lush sets, moody lighting, and original music by the composer Zoë Blade" and opined of her videos that "The most spectacular attraction [...] is Wynn herself."[15] Polygon named her video on incels one of the ten best video essays of the year 2018.[5] In May 2019, she topped the Dazed 100 list, which ranks people who "dared to give culture a shot in the arm."[18]

In September 2019, Wynn described on Twitter feelings of awkwardness when asked in some contexts to describe her preferred gender pronouns.[19] The tweets were criticized as dismissive of non-binary people who use pronouns other than "he/him" and "she/her".[20] Contrastingly, professor Lal Zimman opined about pronoun introductions, "Wynn is absolutely right that people engage with that practice in ways that can be somewhat problematic".[19] Following negative reaction, Wynn deactivated her Twitter account for a week, then posted an apology.[20] She later stopped using Twitter.[21]

In October 2019, Wynn's video "Opulence" featured a quote from John Waters read by transsexual porn star Buck Angel,[22] whose views on transgender people attracted widespread criticism, including by some who see Angel's views as "transmedicalism".[20][22] Wynn was criticised for featuring Angel, including by journalist Ana Valens. In addition to criticism, Wynn and YouTubers associated with her were widely harassed.[20][22] Wynn's January 2020 video "Canceling" addressed both criticism and harassment of her, and the broader context of perceived "cancel culture". It was praised by Robby Soave of Reason.[23]

Personal lifeEdit

Wynn is a transgender woman, a matter that features heavily in her videos, and began her gender transition in 2017.[4] Wynn previously identified as genderqueer.[24][25] She is a feminist and a socialist.[11][13][17][26] As of 2017, she resides in Baltimore, Maryland.[4]


  1. ^ a b @ContraPoints (July 19, 2018). "Alright, alright astrologers. October 21, 1988. 8:00 AM. Arlington, VA. Tell me about my soul" (Tweet). Archived from the original on March 30, 2019 – via Twitter.
  2. ^ a b c d e f g h Hall, Jake (April 9, 2019). "ContraPoints Is the Opposite of the Internet". Vice UK. Retrieved April 9, 2019.
  3. ^ a b Fleishman, Jeffery (June 12, 2019). "Transgender YouTube star ContraPoints tries to change alt-right minds". Los Angeles Times. Retrieved June 13, 2019.
  4. ^ a b c d e f g Singal, Jesse (October 30, 2017). "This YouTuber Is Figuring Out How to Counter the Alt-Right's Dominance of the Site". New York Magazine. Retrieved July 17, 2018.
  5. ^ a b Schindel, Dan (December 28, 2018). "The best video essays of 2018". Polygon. Retrieved December 28, 2018.
  6. ^ Reeve, Elle (March 14, 2019). "Meet the YouTube star who's de-radicalizing young, right-wing men". Vice News. Retrieved March 15, 2019
    • In the video at 02:42:
      Reeve: "Natalie quit a philosophy PhD program in 2015..."
      Wynn: "Dropped out of grad school. 'I'm going to write fiction!' That didn't go anywhere. I wasn't driving Ubers. Just teaching piano lessons, being a paralegal, doing copywriting."
  7. ^ N.B. (December 20, 2018). "The transgender populist fighting fascists with face glitter". The Economist. Retrieved December 28, 2018.
  8. ^ Herrman, John (August 3, 2017). "For the New Far Right, YouTube Has Become the New Talk Radio". The New York Times Magazine. Retrieved July 17, 2018.
  9. ^ Kronfeld, Ezra (May 8, 2018). "ContraPoints on YouTube, Social Justice, and Transphobic Feminists". Out Front. Retrieved July 24, 2018.
  10. ^ a b Neiwert, David (September 18, 2018). "Is that an OK sign? A white power symbol? Or just a right-wing troll?". Southern Poverty Law Center. Retrieved November 13, 2018.
  11. ^ a b c d e Robinson, Nathan J. (May 6, 2018). "God Bless ContraPoints". Current Affairs. Retrieved July 17, 2018.
  12. ^ a b VanDerWerff, Emily (December 20, 2018). "TV Club: YouTube's ContraPoints and Hulu's Puppy Prep". Slate. Retrieved September 23, 2019.
  13. ^ a b c Cross, Katherine (August 24, 2018). "The Oscar Wilde of YouTube fights the alt-right with decadence and seduction". The Verge. Retrieved August 25, 2018.
  14. ^ Reeve, Elle (March 14, 2019). "Meet the YouTube star who's de-radicalizing young, right-wing men". Vice News. Retrieved March 31, 2019.
  15. ^ a b Mark, Clifton (January 6, 2019). "ContraPoints Is Political Philosophy Made for YouTube". The Atlantic. Retrieved January 9, 2019.
  16. ^ Featherstone, Liza (June 7, 2018). "I Think My Friend Is a Jordan Peterson Fan. What Should I Do?". The Nation. Retrieved July 17, 2018.
  17. ^ a b Marantz, Andrew (November 19, 2018). "The Stylish Socialist Who Is Trying to Save YouTube from Alt-Right Domination". The New Yorker. Retrieved November 19, 2018.
  18. ^ Bulut, Selim (2019). "ContraPoints". Dazed. Archived from the original on May 1, 2019. Retrieved May 2, 2019.
  19. ^ a b Mahdawi, Arwa (September 13, 2019). "He, she, they ... should we now clarify our preferred pronouns when we say hello?". The Guardian. Retrieved January 6, 2020.
  20. ^ a b c d Earl, Jessie (October 21, 2019). "What Does the ContraPoints Controversy Say About the Way We Criticize?". Retrieved January 6, 2020.
  21. ^ @ContraPoints (November 6, 2019). "Alright y'all. I've had enough of this for a lifetime. I'll leave the account up so no one else gets the @, but this is my last tweet. Love to all, but especially to non-binary people, who I will never stop supporting and loving. Goodbye" (Tweet) – via Twitter.
  22. ^ a b c Asarch, Steven (October 21, 2019). "YouTuber ContraPoints Attacked After Including Controversial Buck Angel in Video". Newsweek. Retrieved January 6, 2020.
  23. ^ Soave, Robby (January 2, 2020). "Leftist YouTuber ContraPoints Explains Why Cancel Culture Mobs Should Drop the Pitchforks". Reason. Retrieved January 7, 2020.
  24. ^ Bergner, Daniel (June 4, 2019). "The Struggles of Rejecting the Gender Binary". The New York Times. ISSN 0362-4331. Retrieved June 9, 2019.
  25. ^ ContraPoints (March 31, 2017), I Am Genderqueer (And What the #@%! That Means), retrieved June 9, 2019
  26. ^ Miller, Hallie. "This Baltimore YouTube star wants to change minds about transgender issues, one absurd costume at a time". The Baltimore Sun. Retrieved November 5, 2019.

Further readingEdit

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