Natalie Wynn, known by her YouTube channel "ContraPoints," is one of the most notable philosophers and YouTubers today. Her approach to exposing social injustice and status quo is to "meme her way up to the moral high ground".
Most of her older videos started out with satirical intros and Wynn breaking down the subject she was currently discussing. The current format that made her channel most successful revolves around Natalie playing out different characters, representing viewpoints of different people. With this format she's able to portray some absurd philosophies, expose bigotry or offer insight. Sometimes she even defines an issue within society that can't just be resolved by choosing one side, like in the "The Aesthetic" video.This allows her to distance or even isolate her own views from a certain topic and enables healthy discussion in the comment section. By cutting out her emotions and personal ideas, the dialogues between characters are treated differently by the audience - they induce less emotional responses and encourage thinking. The viewer doesn't see a person trying to convince them, but observes an exchange between two different characters. In turn, suggesting who is wrong and who is right (or is there a conundrum?) is made easier for Natalie, and as she targets far-right Internet users, she amplifies the videos with popular memes and slogans to appear less hostile. There are many accounts of people whose minds were changed by ContraPoints content.
If you are a progressive person interested in understanding more about problems our society faces (Natalie doesn't talk exclusively about trans issues), you definitely should check out her channel.
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