This chapter critically examines the rise of extreme misogyny through the Incel movement, the manosphere and online influencers. It explores why negative and damaging narratives resonate with young men and boys and how they reflect systemic, multi-layered misogyny within society. The discussion highlights how digital age masculinities have created a critical juncture which fosters harmful attitudes toward women and worsening mental health outcomes for young men. It underscores the urgent need for realistic, proactive work with boys and young men and addresses the interplay between online and offline worlds that normalize abusive behaviours and extremist views.