This paper presents a longitudinal insight into the experiences of "Adam," a young boy who lives with his single-parent father (a farmer and builder) in a rural working-class community on the outskirts of a provincial town in Tasmania, Australia. Adam's story juxtaposes my representations of him as an eight year old in 1999 and as a 12 year old in 2003. Such longitudinal analysis highlights how increasing mismatches between Adam's home and school life, and mismatches between hegemonic masculinity and formal schooling, interact to amplify issues of school disengagement and alienation. Adam's external expressions of masculinity, and in particular his concerted efforts to subvert and sabotage official school cultures and practices, are explored as issues of power, masculinity, class and rurality.