The purpose of this study is to explore the challenge of 360-degree leaders and its implications for manager leadership in Fun-Fun Cultural Enterprises. 360-degree leadership was first proposed by John C. Maxwell as the theoretical basis. He argues that 99% leadership concerns managers leadership rather than executive leadership. He also believes that 360-degree leaders influence people at every level and add value to others from wherever you are in the organization. At present, Cultural Enterprises have more difficulties in running their business than in the past as a result of the impact of low birthrate and keen competition from the same industry. Middle managers in Fun-Fun Cultural Enterprises would face many trials and challenges and have to remove the leadership myth accumulated over the time. By using the strategy of 360-degree leadership, the middle managers will be well-prepared to face new challenges. Finally, the research analysis can provide inspiration further to guide the Fun-Fun Cultural Enterprises in the right direction in order to be an excellent school.