As humor has been found to have a positive influence on employees’ well-being, work performance, and job satisfaction, it is essential for leaders to utilize humor in the workplace. The ability to use appropriate humor depends on how much leaders understand organizational cultures and others. Two hypotheses are investigated: (1) Politically skilled leaders use more affiliative/positive humor than others and promote a positive humor climate and (2) Social Astuteness (a dimension of Politically Skill) has the highest correlation to leaders’ positive humor styles. Politically skilled leaders were found to also use positive humor styles such as affiliative and self-enhancing humor and avoid aggressive humor. Leaders’ perceived level of being sincere and influencing others had stronger correlations to their perceived positive humor than their ability to assess situations.