This chapter explores the meaning of success in Jo Hyun-tak’s phenomenally successful SKY Castle (2018) and Seiji Kishi’s anime adaptation of Assassination Classroom (2015–2016). Both works question the values of parents, peers, and wider society, as they participate in the rat race of making “successful” children. However, they also focus on the failures of the children to demonstrate how to achieve a different form of success by reclaiming one’s humanity and childhood. This chapter argues that these texts expose the failures of a fraught system by foregrounding repeated academic and social failures through which the characters succeed at becoming “human.”