To play is a legitimate need of urban citizens, and it is therefore important to enable play in cities and to plan for making cities playable. The playable city is not dependent on the digital technologies offered by the smart city. The playable city “happens” when a city offers suitable (playful) affordances and citizens engage in and make use of them. This ultimately implies that also ‘non-smart’ cities can be playable (and may indeed already be so). In this chapter we explore the intersection of playable and sustainable cities. We argue that the playable city can be placed within the realm of what the sustainable city should be and should aim for. The issue of whether this is achieved by applying digital technologies thus becomes decentred, even though digital technologies at the same time could open up for new and exciting possibilities. Key is to ensure that the playable city is a sustainable city and we should therefore aim for designing and building sustainable playable cities.