In showcasing entrepreneurialism, recent commercially successful Bollywood movies follow a different course of representing employment, youth, the State and the market. The five movies, discussed in this paper, stimulate entrepreneurial culture and bring social, economic and cultural recognition to skills that have often been considered ‘mundane’, uncelebrated and even denounced. As showcased in these movies, unlike the Bollywood-represented youth of earlier decades, the young protagonists– male as well as female– neither confront the State for employment nor utilize the State support or family capital or formal technological and managerial training. Rather they look for employment and business opportunities in the ever-growing service sector and achieve success by virtue of possession of ‘mundane skills’ which they combine with their aspirations, entrepreneurial qualities and ethics. These movies also suggest that even if one is a low achiever in formal education and deficient in terms of acquisition of skills as demanded in the new economic sector, success can be achieved. Highlighting contradictions of the job market and cultural values associated with or detached from entrepreneurialism, this paper explores representations of sites, ideas, agencies and discourses of employment through trials and tribulations of protagonists as shown in the movies; and the way they break norms, values and preferences of employment, especially of the middle-class families.