Symbolic interactionists recognize how selves transform for better or worse. When transforming for worse, or going bad, selves often stay bad, owing to societal response. In this article, we examine fictional characters from popular media (specifically, Michael Corleone from The Godfather trilogy and Walter White from Breaking Bad) and a nonfictional athlete (Lance Armstrong) to discuss staying bad as self-conscious choices made by those who go bad. Using Athens’ depiction of self transformation and adding the notion of particular trajectories (teleological, immersed, and ideational), we compare and contrast the characters’ transformations from noble, or potentially heroic, to unapologetically blemished. Our analogic connection depict patterns of development that stress the fundamental importance of agency in regard to processes of staying bad, even when such agency appears self-destructive.