The Dark Triad of personality is composed of narcissism, psychopathy, and Machiavellianism. Despite the common belief that these traits are undesirable, the media is awash with characters that embody the Dark Triad. Characters like Gregory House, M.D., Batman (a.k.a. the Dark Knight), and James Bond all embody these traits and are some of the most popular media franchises today. As entertaining as these characters are, they provide us with a window into the dark side of human nature. Instead of treating the dark side of human nature as inherently maladaptive, we provide an alternative view that, despite their costs, traits like these can confer reproductive and survival benefits for the individual. In so doing, we review the research on the Dark Triad traits and provide a theoretical account for how these traits can confer some positive benefits. To facilitate comprehension, we provide examples taken from the media to show how evolutionary psychology and popular culture intersect.