In the contemporary tourism sector, entertainment is a particular type of service that is increasingly provided by specialised categories of tourist and leisure workers, such as (adventure) sport instructors, tour guides or reps, or 'pub crawling' cicerones. However, little attention has been paid so far to the complex intermingling between work and leisure that sustains the routine 'working leisure' practices of this 'entertainment staff'. By building upon the Foucauldian concept of biopower and Hardt's notion of affective labour, this article examines how entertainment is routinely generated as a service by tourist entertainers in an enclosed tourist resort in Italy. In particular, an in-depth qualitative analysis, combined with an account of a personal experience, was used to structurally frame tourist entertainers' daily 'playful working' practices into three interrelated and functionally complementary dimensions: regimentation, hostessing and experiential rewards. The findings show that entertainment, and hence a successful tourist experience, is effectively (re)generated only when 'working (through) leisure' practices both constrain and gratify the workers. This result corroborates the ambivalence of entertainment as biopolitical affective labour that is a subjugating but also a liberating practice.