To succeed in growing and scaling hospitality organizations, leaders have been portrayed as necessary for full development of hotel employees’ exceptional service. Grounded in emotions as social information theory, our research uncovers how and when daily leader affiliative humor serves the function of spurring hotel employee daily customer-oriented prosocial behavior. Across two time-lagged experience sampling methodology studies, the results from multilevel path analysis indicated that daily leader affiliative humor leads to decreased daily hotel employee inauthenticity, thereby improving daily hotel employee customer-oriented prosocial behavior. We further found that the benefits of leader affiliative humor are amplified when hotel employee perspective taking is higher as opposed to lower. Altogether, our study paves the way for promising future endeavors of promoting hotel employee customer-oriented prosocial behavior, and yields practical insights that assist hospitality organizations in delivering more satisfying customer service.