This dissertation argues that between 2006 and 2016, in a context of rising tolerance for sex workers, economic shifts under neoliberal capitalism, and the normalization of transactional intimate labour, popular culture began to offer new and humanizing images of the sex worker as an entrepreneur and care worker. This new popular culture legitimatizes sex workers in a growing services industry and carries important de-stigmatizing messages about sex workers, who continue to be among the most stigmatized of women workers in the U.S. These new representations challenge stereotypical portrayals of sex workers – as immoral criminals or exploited victims – that support conservative and patriarchal ideologies. Drawing upon feminist theories of sex work, labour theory, and feminist media studies methodology for exploring the nexus of gender, sexuality, and popular culture, this dissertation examines feature films, TV series, and TV and online documentaries that depict five sex work occupations – erotic dancers, massage parlour workers, webcam models, call girls, and sex surrogates – to illustrate the new figure of the sex worker as entrepreneur and care worker under neoliberal capitalism. By emphasizing sex workers’ agency to choose their work, dignifying their skills, underscoring sex work as a means of economic mobility, and highlighting the positive contributions sex workers make to their clients’ lives, these popular culture representations challenge the anti-sex work position espoused by conservative patriarchal ideology and prohibitionist feminists. Some of these new representations, however, intertwine with a neoliberal post-feminist sensibility that frames empowerment as realizable through individualism and the market alone, rather than in collective ways, and pose few concrete solutions to the challenges faced by sex workers today, namely criminalization. Even so, this dissertation argues that these emerging twenty-first century representations of the sex worker as entrepreneur and care worker are progressive and mark a growing social tolerance for the idea that, for some women, sex work is legitimate work.