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Fairy tales and their movie counterparts have, for decades, been a means of socialising children and audiences regarding gender (e.g., Shewmaker, 2015; Whitley, 2013). Specifically, Disney movies that portray fairy tales have strongly influenced how young children learn gender roles and gendered behaviours, yet deeper examination is needed of how Disney portrayals of masculinities have evolved among these films and across character type to understand how Disney may be reflecting or impacting dominant representations of masculinity that privilege certain identities and characteristics over others (Brode, 2016). While previous work has examined Pixar films as socio-culturally meaningful for representations of boyhood that remain grounded in traditional, hegemonic notions of masculinity (Wooden & Gillam, 2014), this chapter adds to the body of work by employing a critical content analysis of Disney films from Snow White and the Seven Dwarfs to Disney's most recent addition of Strange World to answer the questions about how masculinities are portrayed. Through answering these questions of evolved representation throughout close to a century amount of work, we contribute to scholarship that attempts to understand media influences on boyhood culture, which is considered in crisis due to overemphasised representations of powerful, strong male characters that hide their emotions (Brode, 2016; Wooden & Gillam, 2014).