This essay will analyse two films which take up the relation between modern Wales and Welsh implication in colonialism, which problematises Wales’s own status as a country settled by the English. These two films revisit the Welsh settler communities of Patagonia, known as Y Wladfa, and the ones which did not historically come into being in North America. These films are projects of the Welsh pop/rock artist Gruff Rhys, whose solo work and that of the Super Furry Animals use both English and Cymraeg. Seperado! and American Interior are both documentary road movies, following Rhys as he travels to Patagonia and the United States respectively, in search of family and historical figures that connect contemporary Wales with earlier historical migrations. The essay will consider the playful, fluid masculine subjectivity of Gruff Rhys – who uses disguises, plastic helmets, and puppets in the films – as a revision of traditional Welsh working masculinities. The essay works through the mobile masculinities presented in these films in relation to encounters between popular and traditional music, and music’s potential to articulate new, hybrid Welsh masculinities which counter narratives of trauma and loss, or nostalgia for an imaginary homeland.