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Bailey began his career working for Disney, animating on several of their major films of the 80s and 90s. He has also directed the animation of several animation projects. In 2005, Bailey wrote and illustrated Buzzboy/Roboy Red/Major Damage Triple-Frosted Fun Comics!, winning the Russ Manning Promising Newcomer award.
In 2017 his directorial debut, Blazing Samurai, will be released.