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We propose that a key reason why the workplace gender revolution has stalled (England, 201010) is that work remains the site of masculinity contests among men. In this chapter, we outline a theoretical framework for thinking about work as a masculinity contest, beginning with a brief review of scholarship on masculinity and exploring how the workplace is a context in which men feel particular pressure to prove themselves as “real men”. We identify different dimensions of masculinity along which employees may compete and how this competition may differ by work context. We propose that organizations with Masculinity Contest Cultures (MCCs) represent dysfunctional organizational climates (e.g. rife with toxic leadership, bullying and harassment) that are associated with poor individual outcomes for men as well as women (e.g. burnout, low organizational dedication, lower well-being). We review initial research into MCCs and end with a discussion of the contributions made by conceptualizing work as a masculinity contest and directions for future research.