Although pursuing fun seems contradictory to work, it may yield beneficial outcomes for not only employees but also leaders in the workplace. The present paper aims to bridge the gap between the workplace fun/play literature and leadership research by introducing the concept of leader fun pursuit and examining its influence on followers' evaluations. Moreover, drawing on the dual perspective model of social evaluation and expectancy violation theory, we examine the effects of leader fun pursuit on followers' perceptions of leader attributes and evaluations of leadership, and posit a gender‐contingent boundary condition. We conducted three studies to develop a scale and examine our hypotheses. Study 1 (four samples, total N = 734) developed a four‐item scale to measure leader fun pursuit and established its reliability and validity. Study 2 (N = 309) used a multi‐wave design to examine the full model. Study 3 (N = 279) used a vignette‐based experiment to strengthen the internal validity of our conceptual model. We found that leader fun pursuit generally enhances followers' evaluations of the leader, and this effect was especially pronounced for female leaders. Overall, we introduce a novel approach to effective leadership and examine the gender differences therein.