Reflecting on the aesthetic trajectory of the idea of social mobility in Hindi cinema and situating such film texts within the long history of the optical relation between cinema and the city, this article argues that the film Gully Boy’s (2019) quest is anchored within neo-liberal freedoms, albeit topped with a laudable linguistic experiment. In comparison with the social mobility films of the last three decades, the film is marked by certain key departures and new blind spots, which occasion a rethinking of popular culture, particularly due to its increasing over-reliance on the attention economy of social media.