Since its inception, the Olympic Movement has had a strong culture mandate, with “sport, culture and education” being presented as the essential pillars of Olympism in the Olympic Charter. Dedicated cultural programs—now called the Cultural Olympiad—have been a compulsory requirement at the Olympic Games since 1912; artists have always been welcome contributors to the Olympic narrative, and cultural values have informed the development of Olympic rituals from the outset. Despite this, John J. MacAloon and others have noted the lack of a coherent cultural policy framework within the movement and have debated the diversity and local sensitivity of the International Olympic Committee's cultural mandate and portfolio. This article reviews the significance of MacAloon's reflections on this subject since 2000 and interrogates the value of recent developments such as the role of culture within Agenda 2020, changes in the composition of the IOC Cultural and Olympic Heritage Commission, and the evolving positioning of the Cultural Olympiad as the leading contribution of Olympic host cities into the movement's cultural offer. The article concludes with reflections on the potential and challenges for fully inclusive, timely and representative Olympic cultural policies going forward.