The YouTuber ContraPoints, also known as Natalie Wynn, is a fascinating and complicated artist who is taking the video essay genre to new heights with videos on politics, philosophy, and culture. This paper analyzes her videos Incels (2018) and Canceling (2020) within the context of the essay film and video essay genres, while also exploring what ContraPoints is and why the project’s message is prominent in 2022. However, some of the tools she uses to explore video topics, such as empathy and compassion, are seen as faults by some. While Wynn’s videos started out by examining contemporary issues, her fame has grown — bringing more meta or self-referential elements to the forefront of her artistry. While she may have started her YouTube career by making videos about politics and philosophy, she has had to to use her talents for defending herself online, particularly in relation to her controversies around non-binary identity. Ultimately, this paper argues that Wynn, through the use of performance, mise-en-scène, personality, postmodernist qualities, and dialogue, has been successful not only in raising and exploring questions of today’s cultural and political debates, but also showcasing Wynn as an artist and person.