This study examines the role of humor in leadership communication and its varying impacts across Eastern and Western cultural contexts. The historic representation of humor is predominantly Western-centric; Humor is portrayed as a valued asset in Western leadership, contributing to perceived warmth, likability, and team performance, and an undesirable behavior in Eastern cultures, where the lack of seriousness of humor is believed to be associated with social impropriety. This paper explores how humor in leadership is perceived when delivering negative feedback to subordinates in different cultural contexts. Utilizing the benign violation theory and the concept of low- to high-context communication, the research highlights the complex dynamics of humor in leadership across different cultural landscapes and reveals that humor can be rewarded more in Eastern culture than Western culture. The findings emphasize the need for a culturally sensitive approach in leadership communication, recognizing that humor’s effectiveness and appropriateness depend significantly on cultural context. This study contributes to a deeper understanding of humor's multifaceted role in leadership and interpersonal dynamics globally.