Like many of us, the urban planning strategy game "SimCity" was an obsession for Diana Regan growing up. When she published YouTube videos about a modern incarnation -- "Cities: Skylines" and its sequel -- she grew a loyal audience around the games.

But she was more interested in using these sims for social commentary about urban design, capitalism, politics, and absurdist online culture. One problem: Her audience HATED it. That is until one of her TikToks about corporate cities went viral and inspired her to return to YouTube to expand the work into robust video essays.

These days, Diana works full time as a video creator, covering a wide range of topics and painting with all sorts of surrealist brushes: video games, travel videos, memes, archival footage, and AI-generated voices of historical figures saying the darndest things.

Diana sits down with Matt to discuss her singular creative style and how she overcame the limitations of social video platforms that only reward you for doing the same things over and over.

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59 Cities By Diana: Making Absurd Video Game Neighborhoods Became Her Fulltime Job