Skip to content

Natalie Wynn and transgender people

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


Wynn was born on October 21, 1988 in Arlington, Virginia. 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. Wynn did gig work before becoming a YouTuber 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

  • The Witch Trials of J.K. Rowling
  • The Hunger
  • Envy
  • J.K. Rowling
  • Voting
  • Justice
  • Cringe
  • Shame
  • Canceling
  • Opulence
  • Men
  • “Transtrenders”
  • Beauty
  • Gender Critical
  • The Darkness
  • “Are Traps Gay?”
  • The Apocalypse
  • Pronouns
  • The Aesthetic
  • Incels
  • The West
  • Tiffany Tumbles
  • Jordan Peterson
  • What’s Wrong with Capitalism (Part 2)
  • America: Still Racist
  • Autogynephilia
  • What’s Wrong with Capitalism (Part 1)
  • Violence
  • Degeneracy
  • The Left
  • Decrypting the Alt-Right: How to Recognize a Fascist


Robinson, Nathan J. (May 6, 2018). God Bless ContraPointsCurrent Affairs. [archive]

Cross, Katherine (August 24, 2018). The Oscar Wilde of YouTube fights the alt-right with decadence and seductionThe Verge. [archive]

Marantz, Andrew (November 19, 2018). The Stylish Socialist Who Is Trying to Save YouTube from Alt-Right DominationThe New Yorker. [archive]

N.B. (December 20, 2018). The transgender populist fighting fascists with face glitterThe Economist. [archive]

Mark, Clifton (January 6, 2019). ContraPoints Is Political Philosophy Made for YouTubeThe Atlantic. [archive]

Fleishman, Jeffrey (June 12, 2019). Transgender YouTube star ContraPoints tries to change alt-right mindsLos Angeles Times. [archive]

McCrea, Aisling; Robinson, Nathan J. (June 9, 2019). Interview: Natalie Wynn of ContraPointsCurrent Affairs. [archive]

Nancy Jo, Sales (June 17, 2021). ‘The internet is about jealousy’: YouTube muse ContraPoints on cancel culture and compassionThe Guardian. [archive]

Peabody Awards (2023). ContraPoints: Natalie Wynn (YouTube)


Contrapoints (

YouTube (

Patreon (

Twitter (

Facebook (