Skate films, video clips and media about skateboarding in Asia produced in the West can be a mixed journey, especially in terms of the quality of Asian representation in these productions. When locals in Asia produce the content, we witness the creative interpretation of built environments and Asians’ identities as skaters as a source of pride. A skate crew known as the “Osaka Daggers” in Japan are one such example, who film themselves confidently skating the city with joy, innovation, and style. However, when watching videos made by skateboarders visiting from abroad, feelings of disappointment can quickly surface. The skateboarding remains spectacular but is often accessorized or draped in Orientalist tropes. Asians tend to only appear as naïve, threatening, or generally inferior. This includes images of children in awe, comical or disruptive bystanders, or exasperated interpreters. Studies of skateboarding in Asia, therefore, face the challenge of unpacking the dynamics of mythmaking and racializing representations.