Retracing the social, artistic and intellectual evolution of web-generation animation, this article first introduces the web-gen in more detail and examines its social dynamics, focusing on the networks that made it possible. Then, it moves to the web-gen’s relationship to technology, retracing the emergence of digital animation in anime and its role in a socio-aesthetic shift. This shift is afterward investigated in its critical formulation through close reading of some of the web-gen’s key texts. Finally, I interrogate the web-gen’s legacy, illustrating how its practices spread throughout the Japanese animation industry.