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Natalie Wynn
Wynn in 2020
Personal information
Born (1988-10-21) October 21, 1988 (age 34)
YouTube information
Years active2008–present
  • 1.71 million (main channel)
  • 130,000 (live channel)
Total views
  • 91.6 million (main channel)
  • 4.6 million (live channel)
100,000 subscribers2018[1]
1,000,000 subscribers2020[2]

Last updated: July 20, 2023

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 a wide range of topics such as politics, gender, ethics, race, and philosophy.

Her videos often provide counterargument to right-wing extremists and classical liberals and talk about modern social issues such as class inequality, LGBTQ rights (particularly transgender rights), cancel culture, and modern internet culture.[3] Her videos have received widespread media coverage for their intricately designed sets and costumes and for their darkly humorous tone, which has led The Verge to call her "the Oscar Wilde of YouTube".[4] In recognition of her videos, Wynn won a Streamy Award for "Commentary" in 2020, and was nominated in the same category at the 2021 Streamy Awards.[5][6] In 2022, she became an honoree of a Peabody Award.[7]

Early life

Wynn was born on October 21, 1988, in Arlington, Virginia,[8] and raised in the same state.[9] Her father is a psychology professor and her mother is a doctor.[10][11] After studying piano at Berklee College of Music,[12] she attended Georgetown University and studied philosophy, then enrolled at Northwestern University to pursue a PhD in philosophy, also serving as an instructor.[9][11][13][14] She left Northwestern with a master's degree, saying, "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.[9][15] After quitting her PhD program, Wynn taught piano, and worked as a paralegal, Uber driver, copywriter, and would-be novelist, eventually deciding to begin making video responses to the alt-right and Gamergate on YouTube.[16][17]

YouTube career

Wynn started publishing YouTube videos in 2008, initially focusing on criticism of religion and her position as an atheist and 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.[9][13][18][19] Early ContraPoints videos also covered subjects such as race, racism, and online radicalization.[9]


Wynn uses costumes and colorful sets in her videos.

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.[13][20][21] Wynn's videos often have a combative but humorous tone, containing dark and surreal humor, sarcasm, and sexual themes.[13] She often illustrates concepts by playing different characters who debate one another.[1] The videos have been noted for her production choices such as dramatic lighting, elaborate costumes, and vibrant aesthetics.[22] She borrows some aesthetic cues from drag performance, joking in a 2019 interview that if conservatives were going to call her a drag queen anyway, she might as well "be the most extravagant drag queen on YouTube."[23] In a 2018 interview for The Verge, Katherine Cross notes a significant difference between Wynn in-person and how she presents on YouTube, explaining that the YouTube channel portrays an image of being "blithe, aloof, decadent and disdainful", whereas personally Wynn "can be earnest—and she cares deeply, almost too much."[24]

The video channel is financed through the crowdfunding platform Patreon, where Wynn has been among the top 20 creators on the site.[25][26] As of April 2023, Wynn has about 13,500 Patreon supporters.[27]


Wynn's videos have been praised for their clarity, nuance, and attention-grabbing sense of humor.[1][9] Jake Hall, writing for Vice, called Wynn "one of the most incisive and compelling video essayists on YouTube".[9] In an article contrasting her personal sincerity and her ironic sense of humor, The Verge describes her as the "Oscar Wilde of YouTube."[24] 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."[13] Nathan J. 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."[1]

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.[1][22][28] Her 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.[21] Journalist Liza Featherstone recommends the channel as well, saying that she 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.[29]

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."[30] 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."[28] Polygon named her video on incels one of the 10 best video essays of the year 2018.[14] In May 2019, she topped the Dazed 100 list, which ranks people who "dared to give culture a shot in the arm."[31]

The ContraPoints YouTube channel won Best Commentary at the 10th Annual Streamy Awards.[32]

Pronouns controversy

In September 2019, Wynn described on Twitter feelings of awkwardness when asked in some contexts to describe her preferred gender pronouns.[33] The tweets were criticized as dismissive of non-binary people who use pronouns other than "he/him" and "she/her".[34] 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".[33] Following constant negative harassment, Wynn deactivated her Twitter account for a week, then posted an apology.[34] Shortly after, Wynn's video "Opulence" featured a quote from John Waters read by transsexual pornographic actor Buck Angel,[35] whose views on transgender and non-binary people have attracted criticism, including by some who see Angel's views as being transmedicalist.[34][35] She was criticized for featuring Angel, including by journalist Ana Valens. Wynn, as well as other YouTubers associated with her channel, were widely harassed.[34][35]

Wynn's January 2020 video "Canceling" addressed both criticism and harassment of her, and the broader context of cancel culture. It was praised by Robby Soave of Reason.[36] In a Guardian interview on her January 2021 video "J.K. Rowling", in which she addressed cancel culture again in the context of trans-exclusionary radical feminists, she expressed that she is generally not interested in canceling anyone, and said that valid criticism needs to be handed out constructively so as to educate people.[10]

Personal life

Wynn is a transgender woman, a matter prominently featured in her videos; she began her gender transition in 2017.[10][13] She previously identified as genderqueer.[10][37] 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.[38][17] As of 2017, she resides in Baltimore, Maryland.[13] In 2020, she came out as a lesbian in her video "Shame".[10]


Year Award Category Nominee(s) Result Ref.
2020 Streamy Awards Best Commentary ContraPoints Won [32]
2021 Streamy Awards Best Commentary ContraPoints Nominated [39]
2022 Peabody Awards Interactive & Immersive ContraPoints Won [40][7]


The following list of ContraPoints's videos includes only the ones which are still accessible on the ContraPoints YouTube channel. In February 2020, Wynn set all her videos from before August 2017—when she began her gender transition—to private, stating that they "no longer represent the person I've become".[41] She posted transcripts of the majority of these older videos on her website.[42]

No. Title Run time Original release date
1Decrypting the Alt-Right: How to Recognize a F@scist23:33September 1, 2017 (2017-09-01)
2The Left14:02September 24, 2017 (2017-09-24)
3Degeneracy23:06October 19, 2017 (2017-10-19)
4Violence19:23November 24, 2017 (2017-11-24)
5What's Wrong With Capitalism (Part 1)19:07December 30, 2017 (2017-12-30)
6Autogynephilia48:54February 1, 2018 (2018-02-01)
7America: Still Racist21:11February 28, 2018 (2018-02-28)
8What's Wrong With Capitalism (Part 2)19:56March 31, 2018 (2018-03-31)
9Jordan Peterson28:20May 2, 2018 (2018-05-02)
10Tiffany Tumbles21:08June 2, 2018 (2018-06-02)
11The West23:32July 13, 2018 (2018-07-13)
12Incels35:05August 17, 2018 (2018-08-17)
13The Aesthetic21:23September 19, 2018 (2018-09-19)
14Pronouns31:56November 2, 2018 (2018-11-02)
15The Apocalypse24:52December 1, 2018 (2018-12-01)
16"Are Traps Gay?"44:53January 16, 2019 (2019-01-16)
17The Darkness29:22March 2, 2019 (2019-03-02)
18Gender Critical33:49March 30, 2019 (2019-03-30)
19Beauty30:52May 22, 2019 (2019-05-22)
20"Transtrenders"34:44July 1, 2019 (2019-07-01)
21Men30:35August 23, 2019 (2019-08-23)
22Opulence49:07October 12, 2019 (2019-10-12)
23Canceling1:40:28January 2, 2020 (2020-01-02)
24Shame42:03February 15, 2020 (2020-02-15)
25Cringe1:23:19May 10, 2020 (2020-05-10)
26Justice43:04September 4, 2020 (2020-09-04)
27Voting23:40October 19, 2020 (2020-10-19)
28J.K. Rowling1:29:45January 26, 2021 (2021-01-26)
29Envy1:48:15August 7, 2021 (2021-08-07)
30The Hunger57:34May 28, 2022 (2022-05-28)
31The Witch Trials of J.K. Rowling1:55:04April 17, 2023 (2023-04-17)

See also


  1. ^ a b c d e Robinson, Nathan J. (May 6, 2018). "God Bless ContraPoints". Current Affairs. Archived from the original on April 1, 2019. Retrieved July 17, 2018.
  2. ^ @ContraPoints (August 19, 2020). "gorges to be honest I've been in the depths of a major depressive episode for a couple months and not doing well at all, but 1 million subs has jolted me alive and I'm so grateful for everything, thank you, love you so much" (Tweet) – via Twitter.
  3. ^ Fleishman, Jeffrey (June 12, 2019). "Transgender YouTube star ContraPoints tries to change alt-right minds". Los Angeles Times. Archived from the original on July 4, 2019. Retrieved October 21, 2021.
  4. ^ Cross, Katherine (August 24, 2018). "The Oscar Wilde of YouTube fights the alt-right with decadence and seduction". The Verge. Archived from the original on April 3, 2019. Retrieved September 17, 2021.
  5. ^ "2020 YouTube Streamy Awards Winners: Complete List". Billboard. Archived from the original on April 11, 2021. Retrieved September 20, 2021.
  6. ^ Spangler, Todd (October 20, 2021). "YouTube Streamy Awards 2021 Nominations Announced, MrBeast Leads With Seven Nods". Variety. Archived from the original on October 20, 2021. Retrieved October 21, 2021.
  7. ^ a b "ContraPoints". The Peabody Awards. Retrieved May 10, 2023.
  8. ^ @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.
  9. ^ a b c d e f g Hall, Jake; Brownstein, Billie (April 9, 2019). "ContraPoints Is the Opposite of the Internet". Vice UK. Archived from the original on June 2, 2019. Retrieved April 9, 2019.
  10. ^ a b c d e Nancy Jo, Sales (June 17, 2021). "'The internet is about jealousy': YouTube muse ContraPoints on cancel culture and compassion". The Guardian. Archived from the original on June 29, 2021. Retrieved June 30, 2021.
  11. ^ a b Fleishman, Jeffery (June 12, 2019). "Transgender YouTube star ContraPoints tries to change alt-right minds". Los Angeles Times. Archived from the original on July 4, 2019. Retrieved June 13, 2019.
  12. ^ Kaye, Chris (November 11, 2020). "ContraPoints Talks Twitter, TERFs, and Tasting the 'Ideal Beer'". OCTOBER. Archived from the original on November 13, 2020. Retrieved November 14, 2020.
  13. ^ 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. Archived from the original on July 18, 2018. Retrieved July 17, 2018.
  14. ^ a b Schindel, Dan (December 28, 2018). "The best video essays of 2018". Polygon. Archived from the original on December 29, 2018. Retrieved December 28, 2018.
  15. ^ Contrapoints Is De-Radicalizing Young, Right-Wing Men (HBO), archived from the original on April 26, 2021, retrieved May 7, 2021
  16. ^ Reeve, Elle (March 14, 2019). "Meet the YouTube star who's de-radicalizing young, right-wing men". Vice News. Archived from the original on April 17, 2019. 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 was like driving Ubers. Just teaching piano lessons, being a paralegal, doing copywriting. Just like anything. It was because of [?] dark moment that I even decided to do something as suicidal as make video responses to alt-right people."
    {{cite news}}: CS1 maint: postscript (link)
  17. ^ a b Maughan, Philip (April 14, 2021). "The World According to ContraPoints". Highsnobiety. Retrieved August 3, 2021.
  18. ^ N.B. (December 20, 2018). "The transgender populist fighting fascists with face glitter". The Economist. Archived from the original on March 21, 2019. Retrieved December 28, 2018.
  19. ^ Herrman, John (August 3, 2017). "For the New Far Right, YouTube Has Become the New Talk Radio". The New York Times Magazine. Archived from the original on March 23, 2019. Retrieved July 17, 2018.
  20. ^ Kronfeld, Ezra (May 8, 2018). "ContraPoints on YouTube, Social Justice, and Transphobic Feminists". Out Front. Archived from the original on July 25, 2018. Retrieved July 24, 2018.
  21. ^ 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. Archived from the original on June 16, 2019. Retrieved November 13, 2018.
  22. ^ a b St. James, Emily (December 20, 2018). "TV Club: YouTube's ContraPoints and Hulu's Puppy Prep". Slate. Archived from the original on January 20, 2019. Retrieved September 23, 2019.
  23. ^ McCrea, Aisling; Robinson, Nathan J. (June 9, 2019). "Interview: Natalie Wynn of ContraPoints". Current Affairs. Archived from the original on April 7, 2020. Retrieved February 1, 2020.
  24. ^ a b Cross, Katherine (August 24, 2018). "The Oscar Wilde of YouTube fights the alt-right with decadence and seduction". The Verge. Archived from the original on April 3, 2019. Retrieved August 25, 2018.
  25. ^ Sales, Nancy Jo (June 17, 2021). "'The internet is about jealousy': YouTube muse ContraPoints on cancel culture and compassion". The Guardian. Archived from the original on June 17, 2021. Retrieved June 17, 2021.
  26. ^ Reeve, Elle (March 14, 2019). "Meet the YouTube star who's de-radicalizing young, right-wing men" Archived April 17, 2019, at the Wayback Machine. Vice News. Retrieved March 31, 2019.
  27. ^ ContraPoints. "ContraPoints is creating video essays and short films". Patreon. Retrieved March 19, 2022.
  28. ^ a b Mark, Clifton (January 6, 2019). "ContraPoints Is Political Philosophy Made for YouTube". The Atlantic. Archived from the original on July 5, 2019. Retrieved January 9, 2019.
  29. ^ Featherstone, Liza (June 7, 2018). "I Think My Friend Is a Jordan Peterson Fan. What Should I Do?". The Nation. Archived from the original on April 4, 2019. Retrieved July 17, 2018.
  30. ^ Marantz, Andrew (November 19, 2018). "The Stylish Socialist Who Is Trying to Save YouTube from Alt-Right Domination". The New Yorker. Archived from the original on March 21, 2019. Retrieved November 19, 2018.
  31. ^ Bulut, Selim (2019). "ContraPoints". Dazed. Archived from the original on May 1, 2019. Retrieved May 2, 2019.
  32. ^ a b "10th Annual Nominees & Winners". Archived from the original on October 21, 2020. Retrieved December 12, 2020.
  33. ^ a b Mahdawi, Arwa (September 13, 2019). "He, she, they ... should we now clarify our preferred pronouns when we say hello?". The Guardian. Archived from the original on November 8, 2019. Retrieved January 6, 2020.
  34. ^ a b c d Earl, Jessie (October 21, 2019). "What Does the ContraPoints Controversy Say About the Way We Criticize?". Archived from the original on January 6, 2020. Retrieved January 6, 2020.
  35. ^ a b c Asarch, Steven (October 21, 2019). "YouTuber ContraPoints Attacked After Including Controversial Buck Angel in Video". Newsweek. Archived from the original on January 6, 2020. Retrieved January 6, 2020.
  36. ^ Soave, Robby (January 2, 2020). "Leftist YouTuber ContraPoints Explains Why Cancel Culture Mobs Should Drop the Pitchforks". Reason. Archived from the original on February 16, 2020. Retrieved January 7, 2020.
  37. ^ Bergner, Daniel (June 4, 2019). "The Struggles of Rejecting the Gender Binary". The New York Times. ISSN 0362-4331. Archived from the original on June 18, 2019. Retrieved June 9, 2019.
  38. ^
  39. ^ "11th Annual Streamy Nominees & Winners". The Streamy Awards. December 12, 2021. Archived from the original on December 13, 2021. Retrieved December 12, 2021.
  40. ^ Schneider, Michael (May 9, 2023). "'Atlanta,' 'Better Call Saul' Land Farewell Awards as This Year's 83rd Peabody Winners Are Announced". Variety. Retrieved May 9, 2023. ContraPoints
  41. ^ "Archived Transcript of "TERFs"". ContraPoints. Archived from the original on April 28, 2020. Retrieved May 29, 2020.
  42. ^ "Archived Transcripts". ContraPoints. Archived from the original on May 22, 2020. Retrieved May 29, 2020.

Further reading

External links