This double issue of Digital Culture & Society addresses the complex thematic field of the dialectics of play and labour. We will take a closer look at the problem of play and work from two overlapping, albeit not mutually exclusive, perspectives: laborious play and playful work.The term laborious play points to practices and processes that turn playful activities into hard work. Laborious play happens whenever playfulness turns into work, and may be observed in such activities such as e-sports, excessive play, »goldfarming«, and Twitch gameplay broadcasting, amongst many others.A complementary phenomenon to that of laborious play is the practice and concept of playful work. The promises of a joyful and rewarding working experience have been promoted as »gamification« while critical voices denounce such attempts as ideology, exploitation or simply »bullshit«. Besprochen in:https://colognegamelab.de, 10 (2020)