Some scholars have posited that certain traits associated with psychopathy—namely, fearlessness, boldness, and willingness to take risks—are associated with greater engagement in heroic and altruistic acts; nevertheless, this conjecture has received little empirical attention. We examined the relations among psychopathic traits, heroism, altruism, workplace deviance, and leadership in first-responder (n = 138) and civilian (n = 104) samples recruited by means of an online platform. Across samples, fearless dominance, boldness, sensation seeking, and several other psychopathy-related variables were positively and significantly associated with everyday heroism and altruism. First responders scored significantly higher than did civilians on measures of psychopathy, fearlessness, boldness, heroism, and altruism, and reported significantly greater workplace deviance and participation in leadership activities. Our results support previous suggestions of ties between psychopathic traits, especially fearlessness and heroism, although they leave unresolved the question of why certain antisocial and prosocial behaviors appear to covary.