This paper studies the engagement of urban elderly adults with popular music from their youth as one mode through which they negotiate the multiple personal and social shifts associated with aging. It draws upon ethnographic research in the city of Ahmedabad, India, with senior citizens who listen to and sing ‘old’ Hindi film songs (‘puraane gaane’)—the repertoire of Hindi film songs from the mid to late twentieth century. For these participants, the repertoire evokes nostalgia, offers solace and animates music-centered sociability. The paper has two related concerns. One, it explores how these senior citizens actively attempt to redefine their identities in their old age by cultivating singing and listening as ‘serious leisure’ (Stebbins 2001), even as they manage societal and domestic expectations related to age/gender, personal losses, and empty nests. Two, it examines the diverse modalities through which these songs—which are anywhere between thirty and eighty years old—have sustained as a cultural resource for almost two generations of elderly Indians. More broadly, the paper locates these musical activities within the present moment which brings together recent music-related technologies (mobile phone Karaoke apps, small Karaoke studios), and implicit discourses about ‘successful aging’ that encourage senior citizens to turn towards leisure activities (Samanta 2023).