“So, I used to be, little bit of a Man. I’m not proud of it.. We all make mistakes!”Says Natalie Wynn in her 2018 XOXO festival presentation. Natalie Wynn is a transsexual YouTuber known for her B-listing Youtube channel Contrapoints. Flashing a style of her own, she is instantly recognizable for her soft lit videos, colorful characters abundant in a flair of bourgeois and sometimes cringe worthy sex appeal. She discusses controversial subjects like Marxism, gender dysphoria, politics, Cucks and much more from a leftist angle.

I came across Contrapoints through my best friend Monique Johnson, a feminist, college art teacher who loves debate. Granted my BFF has always had strange tastes, but she really one-upped herself with this one. She sent me a video of Natalie Wynn and I didn’t really know how to process the creature I was watching. At first it was a bit hard for me to sit through the whole video, but I did anyway. Partially because of my upbringing and of family influences distilling a kind of internalized homophobia about my own sexuality, Making me cringe the second I see someone else talk about their own sexuality publicly and comfortably. But then seeing this provocative trans woman talking about the taboos many are too afraid to discuss or even mention, was actually very refreshing.

After really sitting down and watching the full length of one of her many 20 minute videos, I saw that this Frank-N-Furter, transsexual, costumer was actually making great points about hot-button iissues. This video left me curious and wanting more, I started digging around and exploring her channel to see what other kinds of material and content she covers. I came across an XOXO Festival video; A kind of public speaking program/festival based in Portland Oregon, similar to TedTalks. In this video, (Natalie Wynn, ContraPoints – XOXO Festival (2018)) it shows Natalie standing on stage in front of a fairly large crowd of seated patrons, and she discusses her struggles with transitioning, her channel and what it stands for. Natalie, in her earlier career, pursued a Phd in philosophy but she turned away from this pursuit. In her words, “The examined life is actually not worth living”. Prior to her channel, she worked as a Uber driver, piano teacher, paralegal and whatever other job she could manage in the many chapters of her life. At this point, she was in an awkward stage of transition. Not quite a women, in the eyes of society, but also not quite a man, in the eyes of her own psyche.

akrales_180810_2785_0132(Natalie Wynn at her home in Baltimore.)

During this time she had made her channel, Contrapoints, she decided to put to use her education and experience. The channels main purpose was to counter and debate the points made by other videos on the web. Hence the name, Contrapoints. But with the internet being the internet, she dealt with the backlash that comes with going through “second puberty” for the whole online world to see and criticize. Leftist Twitter took to her as a representative for the entire trans community and this was simply unfair. She decided to collaborate with a few different Youtube channels and debaters on their programs discussing trans issues, unknowing of the consequences. While she made excellent points and countered arguments with obvious research and wit, she failed those debates in the eyes of her viewers because she was deemed unlikable due to her appearance.

This damaged her reputation for a while and the leftist side of the internet turned against her. That is, until she took a slight change in direction with her channel by costuming into different personas to discuss the topics she was tackling in a back and forth style of banter. By slipping into a fictional setting of debate, she found a way of putting controversial topics on the forefront for open discussion while dampening the impact of negative criticism on her personal life. Her videos are a boiling pot of heated discussion on what needs to be addressed, asking questions that no one knew needed to be asked. “If you want an honest conversation about race on the internet, here’s what you do. You set your computer on fire, you flee to the forest, you drink a mimosa laced with toad venom and you simply wait for the wolverines to eat your legs.”Says Natalie Wynn in her Youtube video, America: Still Racist. She talks about racial demographics in large cities like Baltimore, where previous practices of racism have in a sense trapped families and future generations of African-Americans. Creating ghettos and making racial demographics in urban areas almost impossible to financially escape, through a process of Restrictive Covenants, Redlining, and Predatory Landing when Jim Crow laws were still in act. This kind of grouping creates hot spots of racial conflict by a means of separating, and this separatism continues to stay prevalent in the U.S. because of past racism.

Natalie takes topics like these, that are heavy in Political jargon, bulky with information that are near impossible to find in the convoluted garbage bins of the internet and breaks them down in a way that makes all of her videos extremely informational and easy to digest. “Contrapoints offers us a sense of what it looks like to combat the emotional appeal of neo-fascists with something similar” (Cross), a critic taken from the website TheVerge.com, reviewing how Natalie Wynn has quickly become the new Oscar Wilde of Youtube by taking on the Alt-Right head on with research, facts and seduction. I’m extremely happy my best friend brought me to this channel and to Natalie Wynn’s content. Her discourse on the material she covers is unique, extremely brainy and funny. Even her earlier content brings up issues that are still relevant to todays issues that other debate channels try, but fail to hit the mark. She always finds a way to resolve and properly untangle the inner workings and complexities of the human condition. In my own opinion, I’d have to say, “Contrapoints is hands down the leading channel in terms of quality content, discourse, and diverse topic discussion on the internet to date“.

Work Cited

     Barbara Brotman. “Decades Later, Black Home Buyers’ Battle for justice back in

spotlight”. Chicagotribune.com. https://www.chicagotribune.com/news/ct-contract-

buyers-league-20150724-story.html. July 25, 2015

Katherine Cross. “The Oscar Wilde of Youtube fights and the alt-right with

decadence and seduction”. August 24, 2018. The Verge.

Leslie Vincent Tischauser. “Jim Crow Laws” Land marks of the American Mosaic.

2012. ABC-CLIO. https://www.abc-clio.com/ PP.8-9.

Natalie Wynn. “Natalie Wynn, ContraPoints – XOXO Festival (2018)”. Youtube.com.

https://youtu.be/0Ix9jxid2YU. Nov 9, 2018.

Natalie Wynn. “America: Still Racist | ContraPoints”. Youtube.com.

https://youtu.be/GWwiUIVpmNY. Feb 28, 2018.

Photo Credit

Amelia Holowaty Krales