Psychopathy is one of the more well-established personality disorders. However, its relationship with the American Psychiatric Association's Diagnostic and Statistical Manual of Mental Disorders (DSM) has been controversial. The purpose of this article is to trace and discuss the history of this relationship from the very first edition of the DSM to the current fifth edition. Emphasized in particular is the problematic relationship of DSM antisocial personality disorder with the diagnosis of psychopathy by Cleckley (1941, 1976) and the Psychopathy Checklist- Revised (Hare, 2003), as well as with the more recently developed models of psychopathy by Lilienfeld and Widows (2005), Lynam et al. (2011), and Patrick, Fowles, and Krueger (2009).