Essentialism is a widely debated facet of philosophy, often focused on the role of women in society. However, not often is research concerned with the role of masculinity within essentialism. To see the effect of and on social influence I will be reflecting the concepts of masculinity and essentialism onto film. This is not previously reflected upon categories, and overall the way that feminism can reflect onto masculinity is something that can be helpful to both genders. I will approach this question through an analysis of the films Billy Elliot (2000) and Dead Poets Society (1989) as a microcosmic story of society’s values. These films will enable me to see complete storylines. Also, I will refer to The Wolf of Wall Street (2013) and Goldfinger (1964), and Skyfall (2012), from the Bond franchise as influential storylines for the viewer. It will be approached under the guise of three methodologies, analytic, interpretive, and historical. Between these, I will proficiently examine the argument of essentialism, the idea of masculinity in relation to this, and finally, the way film can illuminate the way we view masculinity. This will be with specific reference to Diana Fuss’ book Essentially Speaking (1989) to frame the essentialism argument; also using Andrea Waling’s discourse around ‘toxic’ and ‘healthy’ masculinities. The addition of Locke’s idea of ‘nominal’ versus ‘real’ essence and Luce Irigaray’s input on feminism of difference all integrate to form a coherent basis from which to analyse and interpret the selection of films and draw conclusions. The concluding finding is that film is an integral lens through which we can view society and the demonization of femininity that evolves from the negative masculinity we continue to idealise. This is important to explore as previously the literature has fallen short of showing the practical ends film can lead to, and the importance of delineating the way we view essence even if it is a foundational part of knowledge.