This project brings a personality psychological perspective to the debate about why and how so many people sympathize with, or root for, or simply like unambiguously villainous characters. The presentation reports the results of a large-scale online survey (n= 1804) that explores the connections between personality and positive forms of engagement with villainous characters. In particular, it explores whether the personality psychological constructs of Agency/Communion and/or the Dark Triad (consisting of the traits of Machiavellianism, narcissism, psychopathy) predict positive forms of engagements with villainous characters. The results of the survey suggests that the Dark Triad is uniquely predictive of positive forms of engagement with villainous characters.