This exploratory article draws critical insights from Raewyn Connell's The Men and the Boys (2000) to unpack the gendered nature of neoliberal right-wing populist governance in India and America. Connell's prescient work targeted towards forging new theoretical inroads in masculinity studies research, on its conception, continues to provide a vital heuristic model to make better sense of the present condition. This article first situates right-wing populist governance in India and America within the rubric of global neoliberal capitalism. It then unpacks Narendra Modi and Donald Trump's carefully calibrated populist imaging, drawing attention to the surrounding gendered discourses rooted in local and culturally idealized perceptions of hegemonic masculinity. Narendra Modi and Donald Trump's public figuration falls in the “cult of strongman leader stereotype”, characterized by risk-taking translated into perceived virility. Social media and its affordances further prop up their perceived masculine public personas, while affectively inscribing traditional inscriptions of heteronormative masculinity, such as ideas of dominance, as aspirational. Through preliminary research, this article then considers the effects of political masculinities on adolescent masculinities. In conclusion, this article stresses the theoretical relevance of Connell's important work twenty years later.