PurposeThis paper uses the cultural figure of Willy Wonka to explore the archetype of the “boy-entrepreneur”, and what the various film manifestations of Wonka (1971–2023) say about changes in entrepreneurial masculinity. We (1) develop an original conceptualisation of boyhood as creatively, socially and gender liminal, (2) analyse the entrepreneurial archetype using literary theories and (3) provide a novel interpretation of Apollonian and Dionysian masculinity to aid future cultural analysis of founder/innovator depictions in children’s media.Design/methodology/approachOur study conducts a three-stage dramaturgical analysis of the major film adaptations of Roald Dahl’s Willy Wonka (1971, 2005 and 2023). After supplementing the limited literature on boyhood in entrepreneurship with literary and feminist art theory, we identify the significant narrative features which frame the Wonka dramas and produce a framework which tracks thematic changes across the films in terms of the creative, social and gender liminal elements of Wonka’s boy-entrepreneur identity.FindingsOur interpretive analysis reveals a gradual shift in values expressed through Wonka’s boy-entrepreneurialism away from a more hegemonic, Apollonian style of masculinity towards a more Dionysian style embracing emotional expression, intimacy with female characters and kin, and collaborations with nature. Such shifts reflect the growing influence of non-hegemonic entrepreneurial gender expressions, value-driven and relational approaches to new venture creation.Originality/valueThe study contributes to the hugely unexplored area of the “boy-entrepreneur”/“boy-genius”, demonstrating its durability in reality, imagination and popular culture. We provide an in-depth character portrait to provoke further attention to children’s multi-media ways of experiencing early entrepreneurial impressions. We also expand the methodological scope of research on entrepreneurial masculinity beyond real-life founders.
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