The purpose of this study was to explore the relationship between leadership styles (transformational, transactional, laissez-faire) and humor styles (affiliative, self-enhancing, aggressive, self-defeating) of community college presidents. Research has shown that humor and leadership styles are related and that humor may enhance interpersonal relationships between leaders and followers. Participants of this study included 166 community college presidents from 600 randomly sampled institutions belonging to the American Association of Community Colleges. The presidents completed an online survey including a relatively new humor questionnaire, the Humor Style Questionnaire, as well as a leadership questionnaire, the Multifactor Leadership Questionnaire. This study proposed that affiliative and self-enhancing humor would be positively related to transformational and transactional leadership styles; while aggressive and self-defeating humor would be negatively related to transformational and transactional leadership styles. Additionally, it was hypothesized that the four humor styles would be negatively related to the laissez-faire leadership style. In sum, affiliative and self-enhancing humor had a positive relationship with transformational leadership. Self-enhancing humor also had a positive relationship with the contingent-reward subscale of transactional leadership; while aggressive humor was inversely related to transformational leadership and to the contingent-reward subscale of transactional leadership. No significant relationships were found between humor styles and the laissez-faire leadership style. Exploratory analyses were conducted to investigate demographic variables. Females (n = 44) scored significantly higher than males (n = 119) on self-enhancing humor and transformational leadership. Age and years of experience were significantly and negatively related to affiliative humor. Based on the findings of this study, one could suggest that community college presidents may be more likely to utilize affiliative and self-enhancing humor when utilizing transformational and transactional leadership styles. Additionally, presidents may be less likely to utilize aggressive humor when using these leadership styles. The findings support previous research in the general premise that humor and leadership are related. However, the findings of this study also highlight the multiple variations of how these two constructs may be associated and interact. Research should continue with other populations and in relation to humor styles and leadership styles as perceived by others. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]