In positive psychology, humor has been identified as one of 24 character strengths considered ubiquitously important for human flourishing. Unlike the other strengths, humor was a late addition to this classification system and its status as a strength continues to be somewhat controversial. Therefore, the first purpose of this study was to explore the associations between humor and several outcome variables of relevance to positive psychology (happiness, routes to happiness, resilience, and morality). The second purpose was to explore how best to conceptualize and measure humor as a character strength by comparing the Values in Action Inventory of Strengths (VIA-IS) Humor Scale with the Humor Styles Questionnaire (HSQ) in their ability to predict the outcome variables. A sample of 176 participants completed questionnaires assessing the humor and positive psychology constructs. The results indicated that the humor measures significantly predicted most of the outcome variables, supporting the importance of humor in positive psychology. Furthermore, although the VIA-IS Humor scale and positive humor styles on the HSQ showed considerable overlap, the negative humor styles added significantly to the prediction of outcome variables beyond these positive humor measures, supporting the importance of assessing maladaptive as well as adaptive uses of humor in research on positive psychology. These findings suggest that the HSQ may be a more useful measure than the VIA-IS Humor scale in future research in this field.