Raewyn Connell famously theorized hegemonic masculinity, explaining its dominance over femininity and “subordinated” and “marginalized” masculinities. Attending to representations of the latter, we argue that “men in the margin” are commonly wrongly and/or simplistically depicted as regressive and violent in response to their marginalization. Focusing on representations of working-class boys and men, we illustrate the stereotypical treatment of “men in the margin” more broadly, making clear that this goes against Connell's treatment of such men. Conversely, privileged boys and men are commonly held up by critical studies on men and masculinities scholars as paragons of progressive change. The characterization of boys and men in the margin as regressive and patriarchal impedes the ability to address problems like violence, misogyny, and homophobia and overlooks the possibilities for transformation that emerge among marginalized communities.