Masculine sentimentality played an important role in Australian culture in the 1930s and 1940s, as in other places where plaintive country music songs attracted a passionate following. Using ‘Australia's Singing Cowboy’ Tex Morton as a case study, we show that this sentimentality became part of both the bush tradition and country music in Depression- and Second World War-era Australia, associated with the bushworker or rugged ‘lone hand’. This sentimentality was deeply problematic from a feminist perspective, as indeed was Morton's personal life. It romanticised what he called ‘the sins of the son’; that is, the lone hand's inability to do right by those he loved. It also glamorised his tears and self-pity, treating them as signs of his hardy masculinity. Given the significance of this form of sentimentality both in Australia and elsewhere over the rest of the twentieth century, feminist scholars of popular culture and historians of gender and the emotions need to pay more attention to country music songs about errant sons and lovers from the 1930s and 1940s.