Abstract: Workplace fun is an organizational phenomenon intended to bring cheerfulness and joviality to employees’ daily work-related interactions. Because of its uplifting nature, workplace fun is prevalent in numerous organizations. HRD practitioners use workplace fun to engage employees. However, research has associated workplace fun with employee disengagement as well. Organizational culture potentially explains the different effects of workplace fun on employee engagement. The clan and hierarchy cultures potentially present organizational cultures that can either assist or hinder positive outcomes of workplace fun, respectively Organizations with clan cultures have a family-like feel. Contrastingly, hierarchy cultures have a more stringent and rigid structure. A cross-sectional survey design was utilized to examine the relationship between workplace fun, employee engagement, and two dimensions of organizational culture (clan and hierarchy), while controlling for personality types and five generational cohorts. This study used participants solicited from Amazon’s Mechanical Turk (MTurk) to test if the organizational clan and organizational hierarchy culture moderates the relationship between workplace fun and employee engagement. The results indicated that workplace fun does significantly increase employee engagement. However, neither the clan nor the hierarchy culture had a practically significant moderating effect on the relationship between fun and engagement. Interpretations of the findings, in relation to significant workplace fun literature are presented. Implications for theory, research, and practice are discussed.