Playing with Lowbrow is an art game development/creation project that explores the application of Lowbrow aesthetics to game graphics. The resulting creation, Twinkling Stars Above, is a single-player platform PC game prototype. This paper describes the shared and distinct context of two contemporary art movements important to the creation of Twinkling Stars Above: Japan‘s Superflat and North America‘s Lowbrow. I propose that, given Superflat‘s influence on Japan‘s video game graphics, Lowbrow style could also be applied to video games. Through the theoretical background of the Superflat and Lowbrow movements, and practice-based research, Playing with Lowbrow suggests an opportunity to apply the aesthetics of Lowbrow to contemporary digital games in order to blend aesthetics and push against the conventional definitions of high and low art.