It is no big secret that so-called 'freestyle sports' have become an integral part of today's sports scene. More and more people are rejecting traditional sports and their organisational structures and expressing their individuality in a pluralistic society through a wide variety of movement arts that are largely free from norms, rules and pressure to perform. This paper aims to compare two such sports and highlight any similarities and differences. Skateboarding, a sport that originated in America in the 1960s, is contrasted with parkour and freerunning, a form of training originally designed for military purposes that began in the suburbs of Paris. In both cases, the forms of movement can be described as individual expression and a central element of a lifestyle. The practitioners are constantly on the lookout for new locations in an 'urban space game', which they examine for possibilities for tricks and movements and which ultimately become participants in their movement practice.