Much of the sociological work examining the changing fortunes of working-class young men has emphasized their newly precarious position as well as the “hollowed out” nature of their class subjectivities. By contrast, and echoing work on the adaptability of hegemonic forms of masculinity, this article points to the ongoing salience of working-class masculinities, drawing on longitudinal research with young men in Russia’s Ul’yanovsk region between 2004 and 2013. It examines how young men are able to shift from a position of marginality to one of a complicit, breadwinning masculinity by bringing to bear a variety of social, cultural, bodily, and institutional resources rooted in their class, gender, and ethnic location. This journey also reflects young men’s negotiation of dialogical, moral selves, central to which is their acquired ability to reflect upon different ways of being a man by appealing to wider moral currents within Russian society.