A metaphorical expression of the myth of the American Dream, gambling — institutionalized in casinos or illegal in underground circles — soon became a fixture of masculine film genres such as westerns and gangster films. As a rule, gambling movies, regardless of their genre, are male-driven films, leaving only secondary parts to female protagonists who usually fall into three categories: good luck charms/helpers (The Cooler, 21), trouble-makers (Casino, Gilda) or purveyors of moral standards (Rounders, The Cincinnati Kid). Conversely, in gambling films featuring women in lead roles, actors are more likely to embody addicts (The Lady Gambles, Even Money), entrepreneurs/professionals (Atlantic City, Molly’s Game) and — more rarely — professional gamblers (Gambling Lady), thus contesting the masculine hegemony usually at play in this type of film. Through a diachronic approach based on sociological and historical facts, this article proposes to consider how female-driven gambling films may offer a possibility for female lead actors to reclaim the ‘male gaze’ and somehow reestablish a form of gender equality by portraying tough, smart, pragmatic women in a traditionally masculine environment. Achieving the American Dream or wasting their lives to addiction, these women contradict enduring clichés conveyed by Hollywood and informed by the Hays code during the classical era.