In this paper, I explore male youth sport coaches' use of humour in relation to the reconstruction of masculinities, contributing to an emergent body of literature on the role of humour in coaching. Three creative non-fiction stories developed from my own coaching experiences in a competitive youth football (soccer) academy are used to examine: (1) coaches' reconstruction of hegemonic/esteemed masculinities; (2) coaches' use of humour to encourage re-alignment with hegemonic masculinities, and; (3) coaches' use of (counter-)humour to disrupt hegemonic representations of masculinities. The stories offer sport coaches and educators with a resource to reflect on masculinities, gender relations, and the everyday use of humour within their own contexts.