In the past five decades, a wealth of research has improved our understanding of the individual and sociocultural factors that contribute to sexual aggression perpetration. At the same time, epistemological differences in theoretical approaches to the subject (i.e., evolutionary, feminist) have stymied the study of the topic from multiple perspectives. Informed by feminist and evolutionary perspectives and research on individual differences, this study examined interactions between intermale status challenge and psychopathic personality traits on a laboratory analog of sexually aggressive behaviors among 139 heterosexual men (average 21 years old, 64% white, 26% Hispanic). Results suggest multiple pathways to sexual aggression, with the strongest evidence for the role of interpersonal-affective psychopathic traits in sexual aggression following a competition win, but not loss. Results are discussed to emphasize the importance of both individual-level variables and interpersonal social contexts in shaping sexual aggression behavior.