Both scholars and the popular press have expressed concern regarding the potential prevalence of individuals with psychopathic tendencies in corporate leadership positions and the negative effects they may have on both individual workers and their organizations as a whole. However, research to date has been inconclusive as to whether such individuals are more likely to emerge as leaders or whether they are (in)effective leaders. To clarify the state of the literature, we conducted a meta-analysis on the association between psychopathic personality characteristics and leadership emergence, leadership effectiveness, and transformational leadership. Our results, based on data from 92 independent samples, showed a weak positive correlation for psychopathic tendencies and leadership emergence, a weak negative association for psychopathic tendencies and leadership effectiveness, and a moderate negative correlation for psychopathic tendencies and transformational leadership. Subgroup analyses on methodological factors did not indicate any differences from the main results. However, moderator analyses showed a gender difference in these associations such that psychopathic tendencies in men were weakly positively correlated with leadership emergence and effectiveness and negatively correlated with transformational leadership, while psychopathic tendencies in women were negatively associated with effectiveness and transformational leadership, and largely unassociated with emergence. In addition, small but consistent curvilinear associations were found for all leadership criteria. Overall, these results suggest that concern over psychopathic tendencies in organizational leaders may be overblown, but that gender can function to obscure real effects.