This major research paper investigates the ongoing relationship between anime and otaku culture through four case studies; each study considers a single situation that demonstrates how this relationship changes through different interactions with representation. The first case study considers the early transmedia interventions that began to engage fans. The second uses Takashi Murakami’s theory of Superflat to connect the origins of the otaku with the interactions otaku have with representation. The third examines the shifting role of the otaku from that of consumer to producer by means of engagement with the hierarchies of perception, multiple identities, and displays of sexualities in the production of fan-created works. The final case study reflects on the 2.5D phenomenon, through which 2D representations are brought to 3D environments. Together, these case studies reveal the drivers of the otaku evolution and that the anime–otaku relationship exists on a spectrum that teeters between reality and representation.