Drawing on cultural geographical work on mobilities and landscape, this article examines parkour in Singapore, a context in which everyday mobile practices are conventionally understood to be heavily constrained and disciplined. As an urban mobile practice that involves bodily adaptation to and dynamic interaction with the prevailing built environment, parkour reveals complex relationships between the self and the landscape. For its practitioners, the doing of parkour holds potential not only for reimagining what Singapore’s urban landscape is or can be but also for reconfiguring understandings of themselves. The term landscaping captures the continuous and concurrent shaping of self and landscape through parkour; landscapes affect individual bodies and are actively (re)constituted through embodied movement. The article engages parkour in more-than-representational terms. By segueing between discursive and phenomenological approaches to mobilities and landscape, a dual emphasis on corporeal experience and representational frameworks highlights how both create and/or regulate such mobile bodies and practices within the landscape.