Psychopathic personality (a term that has been largely supplanted in psychologists’ and psychiatrists’ nosologies by anti-social personality disorder) and narcissism are venerable, widely used, and fiercely contested categories of personality disorder. Psychopathic personality was originally delineated in the early years of the 20th century to encompass behavior that was, in experts’ estimation, decidedly not normal but that fit none of the other categories of mental disease. Critics of the diagnosis claimed it was but another label for individuals’ non-conformity with social norms, used to punish the poor and marginal. Narcissism has had an even more tumultuous history than psychopathy. Referring simultaneously to traits considered pathological (grandiosity, exploitativeness, manipulativeness) and to traits thought desirable (high self-esteem, capacity for leadership and authority), narcissism has been at the center of debates over national decline and the character of the modal American for the past half-century. Both categories have also sparked controversy along the trait/ state, dimensional/ categorical divide that flared in the run-up to the publication of the 5th edition of psychiatry’s Diagnostic and Statistical Manual of Mental Disorders in 2013. Thousands of papers have attempted to resolve the ambiguities surrounding both diagnoses, but these ambiguities have proven productive (of research and new knowledge) and are unlikely to be resolved soon.