While sports and music diplomacy between North Korea and South Korea in 2018 revived hopes for peace and reconciliation, it is not so clear what impact exchanges like these have over the long term. This paper traces the historical context of inter-Korean music and sports ventures examining the motivations and reception of them in each half. It argues that sustained music and sports interactions between the Koreas have moved gradually yet decisively towards mutual accommodation. Nevertheless, there is some ambiguity regarding the simultaneous objectives of reaching out to the other side and legitimizing one’s own political system.