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Sporting celebrities have come to hold an increasingly vaunted position within contemporary society and as such, receive ever-increasing media attention. Within Canadian culture, where the sport of hockey is largely considered a mythologized component of identity, hockey players such as the National Hockey Leagues Sidney Crosby are not only frequently represented in the daily media, but are also utilized in promotional and advertising campaigns. In this thesis, I qualitatively analyze media representations and the production of advertising featuring Sidney Crosby. Specifically, I examine the specific case of producing televised advertising campaigns featuring Crosby for sports drink manufacturer Gatorade. I also interrogate the tensions and ambiguities of contemporary conceptualizations of masculinity evidenced in media discourse surrounding Crosby. Ultimately, this study examines how sporting celebrities and discourses of corporate nationalism are produced within contemporary advertising campaigns and the role that cultural intermediaries play in the promotion of particular values and perceptions.