Sense of humor has been identified as a possible factor that leads to riskier behavioral choices, which could, in turn, contribute to health problems and reduced longevity. In previous studies, sense of humor was viewed as a one-dimensional, positive personal quality: the potential impact of maladaptive styles of humor was not acknowledged. The current study assesses both adaptive and maladaptive humor styles and relates them to perceived risk, and to the performance of risky behavior. The results do not support the suggestion that a sense of humor – when considered as a cheerful, carefree, and optimistic orientation – is related to assessments of risk or risky choices. Although humor styles did predict risk perception and risky behavior, it was the maladaptive, aggressive humor style that was related to a lower perception of risk, and higher rates of predicted and actual risky behavior. Humor styles that reflect a positive mindset, and that were predictive of less chronic worry, were not consistently or reliably associated with perceiving situations as less risky or with higher rates of risky behavior. Further research is needed to clarify why an aggressive humor style was predictive of risk assessment and risky choices.