Risk is inherent to playful play, but it’s an area of the play spectrum that is threatened by policy making, social and cultural anxieties and commercial interests. We’ve chosen two perspectives on Risk for this chapter who practice in very different modes: artist and author Sharna Jackson, creating and exploring things like playful cities (artistic commissioning, children’s writing and media) and Professor David Ball’s work championing the benefits of risk at times (through expert consultation on Health and Safety Policy). There’s a playful thread running through all their work.