This double issue of Digital Culture & Society addresses the dialectics of play and labour, taking a closer look at the problem of play and work from two overlapping, albeit not mutually exclusive, perspectives. After the first issue explored the notion of laborious play, this second one studies the concept of playful work. The contributions feature critical inquiries into various phenomena of playful work - ranging from interfaces of play and work in the BDSM subculture over labour in digital gaming to high frequency trading. Alongside the articles, the issue features an interview with Fred Turner, Chair of the Department of Communication at Stanford University. He talks about the Bauhaus in the US, countercultural cybernetics, technology and consciousness, and work in the Silicon Valley.