Chapter 6 takes the cultural youth activity of parkour as its starting. Parkour has so far been described in two different frames of understanding: as a form of social critique and as craftsmanship. On one hand, the parkour runner plays with his or her environment, testing walls, stairs, roofs, etc., by playful trials, turning the normality of moving topsy-turvy, provoking surprises, and creating feelings of playful fun, which on a symbolic-discursive level reveals the suppressive constitution of the capitalistic urban space. On the other hand, the parkour runner in a concentrated and engaged way practically explores and investigates facilities in the urban landscape, their materials, and their challenge in relation to one’s own ability. By touching, feeling, and trying, parkour develops a craft-like relation to obstacles and produces movement success. The two forms of activity interconnect, what normally theoretically is dissociated: craftsmanship as a serious form of work, and play as a free and spontaneous activity of fun. This implies some philosophical challenges: How are the activities of parkour, the concept of craft or work, and the concept of play related to the questions, which human beings put to the world? And if it is the player, who plays, or the play, which makes the human being a player, what does this inversion mean for craftsmanship: The craft making the craftsman?