In discussing a future research agenda for research on men, masculinities, and leaderships, this chapter updates an earlier discussion by Collinson and Hearn (1994) by exploring some of the important new emerging research questions, informed by recent developments in critical studies on men and masculinities (CSMM) and by recent research on critical leadership studies (CLS). While in practice these two areas of research overlap considerably, for these purposes they are discussed separately. When combined together, they provide clear guidance for future research on men, masculinities, and leadership. The implications of some developments in CSMM and CLS are examined by way of the tensions between gender/intersectionalities, local/transnational, embodied/virtual, theory/practice (Hearn, 2014). In this chapter, examples of how an explicitly and critically gendered analysis of men and masculinities is of relevance and use for the study and indeed practice of leaders and leadership is explored.