Natalie Wynn and transgender people

Media coverage and transgender people Reviewed July 19, 2026 4 min read

Natalie Wynn is an American cultural critic whose YouTube channel Contrapoints won a 2022 Peabody Award in the Immersive & Interactive category.

Background

Wynn was born on October 21, 1988 in Arlington, Virginia and grew up in nearby Vienna. Wynn’s parent William is a psychology professor at Georgetown, and parent Marian is a doctor. Wynn has two siblings who also went to Georgetown.

Wynn studied piano at Berklee College of Music, earned a bachelor’s degree from Georgetown University in 2012, and a master’s degree from Northwestern University, then decided not to pursue a doctorate. Wynn did gig work before becoming a video essayist in 2008. Wynn’s work is considered part of “BreadTube,” a loose affiliation of YouTubers who posted videos to challenge right-wing views on subjects.

In 2016, Wynn began the ContraPoints channel. In 2017, Wynn came out as trans and removed all pre-transition videos. In 2020 Wynn came out as lesbian.

Video essays

Wynn is known for criticizing a number of prominent anti-trans figures, including Ray Blanchard, Jordan Peterson, Megan Phelps-Roper, and J.K.Rowling. Wynn has also lampooned segments of the trans community, presenting humorous characters who represent various political factions.

2026

Saw https://www.youtube.com/watch?v=uiGIbdrQjbI

2025

CONSPIRACY https://www.youtube.com/watch?v=teqkK0RLNkI

2024

Twilight https://www.youtube.com/watch?v=bqloPw5wp48

2023

The Witch Trials of J.K. Rowling https://www.youtube.com/watch?v=EmT0i0xG6zg

2022

The Hunger https://www.youtube.com/watch?v=RTRT794IQBg

2021

Envy https://www.youtube.com/watch?v=aPhrTOg1RUk
J.K. Rowling https://www.youtube.com/watch?v=7gDKbT_l2us

2020

Voting https://www.youtube.com/watch?v=t3Vah8sUFgI
Justice https://www.youtube.com/watch?v=smQsfNw_7V4
Cringe https://www.youtube.com/watch?v=vRBsaJPkt2Q
Shame https://www.youtube.com/watch?v=K7WvHTl_Q7I
Canceling https://www.youtube.com/watch?v=OjMPJVmXxV8

2019

Opulence https://www.youtube.com/watch?v=jD-PbF3ywGo
Men https://www.youtube.com/watch?v=S1xxcKCGljY
“Transtrenders” https://www.youtube.com/watch?v=EdvM_pRfuFM
Beauty https://www.youtube.com/watch?v=n9mspMJTNEY
Gender Critical https://www.youtube.com/watch?v=1pTPuoGjQsI
The Darkness https://www.youtube.com/watch?v=qtj7LDYaufM
“Are Traps Gay?” https://www.youtube.com/watch?v=PbBzhqJK3bg

2018

The Apocalypse https://www.youtube.com/watch?v=S6GodWn4XMM
Pronouns https://www.youtube.com/watch?v=9bbINLWtMKI
The Aesthetic https://www.youtube.com/watch?v=z1afqR5QkDM
Incels https://www.youtube.com/watch?v=fD2briZ6fB0
The West https://www.youtube.com/watch?v=hyaftqCORT4
Tiffany Tumbles https://www.youtube.com/watch?v=j1dJ8whOM8E
Jordan Peterson https://www.youtube.com/watch?v=4LqZdkkBDas

2017

What’s Wrong with Capitalism (Part 2) https://www.youtube.com/watch?v=AR7ryg1w_IQ
America: Still Racist https://www.youtube.com/watch?v=GWwiUIVpmNY
Autogynephilia https://www.youtube.com/watch?v=6czRFLs5JQo
What’s Wrong with Capitalism (Part 1) https://www.youtube.com/watch?v=gJW4-cOZt8A
Violence https://www.youtube.com/watch?v=lmsoVFCUN3Q
Degeneracy https://www.youtube.com/watch?v=9BlNGZunYM8
The Left https://www.youtube.com/watch?v=QuN6GfUix7c
Decrypting the Alt-Right: How to Recognize a Fascist https://www.youtube.com/watch?v=Sx4BVGPkdzk

References

Weiss, Max (June 2024). Who Exactly Is Natalie Wynn? Baltimore Magazine https://www.baltimoremagazine.com/section/artsentertainment/natalie-wynn-viral-baltimore-youtuber-profile/

Peabody Awards (2023). ContraPoints: Natalie Wynn (YouTube) https://peabodyawards.com/award-profile/contrapoints/

Nancy Jo, Sales (June 17, 2021). ‘The internet is about jealousy’: YouTube muse ContraPoints on cancel culture and compassion. The Guardian. [archive] https://www.theguardian.com/lifeandstyle/2021/jun/17/contrapoints-natalie-wynn-youtube-interview

Fleishman, Jeffrey (June 12, 2019). Transgender YouTube star ContraPoints tries to change alt-right minds. Los Angeles Times. [archive] https://www.latimes.com/entertainment/la-et-st-transgender-youtuber-contrapoints-cultural-divide-20190612-story.html

McCrea, Aisling; Robinson, Nathan J. (June 9, 2019). Interview: Natalie Wynn of ContraPoints. Current Affairs. [archive] https://www.currentaffairs.org/2019/06/interview-natalie-wynn-of-contrapoints

Mark, Clifton (January 6, 2019). ContraPoints Is Political Philosophy Made for YouTube. The Atlantic. [archive] https://www.theatlantic.com/entertainment/archive/2019/01/contrapoints-political-philosophy-natalie-wynn-youtube/579532/

N.B. (December 20, 2018). The transgender populist fighting fascists with face glitter. The Economist. [archive] https://www.economist.com/open-future/2018/12/21/the-transgender-populist-fighting-fascists-with-face-glitter

Marantz, Andrew (November 19, 2018). The Stylish Socialist Who Is Trying to Save YouTube from Alt-Right Domination. The New Yorker. [archive] https://www.newyorker.com/culture/persons-of-interest/the-stylish-socialist-who-is-trying-to-save-youtube-from-alt-right-domination

Cross, Katherine (August 24, 2018). The Oscar Wilde of YouTube fights the alt-right with decadence and seduction. The Verge. [archive] https://www.theverge.com/tech/2018/8/24/17689090/contrapoints-youtube-natalie-wynn

Robinson, Nathan J. (May 6, 2018). God Bless ContraPoints. Current Affairs. [archive] https://www.currentaffairs.org/2018/05/god-bless-contrapoints