This chapteroffers a detailed and careful analysis of how animation demonstrates the historical specificity, the continuities and discontinuities in racial formations. The transition to sound was ushered in by jazz music and jazz cartoons: fantastic representations of the imagined realms of a black jazz underworld. Some of these cartoons continued in the tradition of blackface minstrelsy. Others, though, trafficked in a relatively more virulent form of racist caricature, visiting fantastic violence on ostensibly black bodies. This chapter charts the complex relationship between cartoon minstrels and racist caricature in 1930s and 1940s animation. Animation, so suited to expressing the impossible, unleashed fantastic versions of blackness and punished them for their power and difference. Both an exception and proof to the rule, this shift in animation practice was integral to and refractive of instability in social and cultural norms around race at that time.