How have cinema's representations of loneliness changed over time, in keeping with the changing technological mediation of loneliness? What can these representations tell us about how the experience of loneliness is made sense of in everyday life? And, crucially, how has cinema's own technicity remediated loneliness in the process of representing it? In order to unpack some of these complexities, this article narrows its focus to a mere two minutes of screen time: the opening of The Graduate (1967), with its iconic representation of a lone character traversing Los Angeles International Airport to the tune of Simon and Garfunkel's 'The Sound of Silence'. The Graduate opens an important window into a particular sociohistorical moment when technologies, techniques, industry concerns and social conditions placed the audio-visual aesthetics of loneliness at the core of American cinema. I interpret this moment as the symbolic beginning of what Robert Kolker has termed 'a cinema of loneliness', a body of films that frequently featured solo drifters at plot level and that were made by directors working in isolation due to the collapse of the old Hollywood studio system. Notably, The Graduate forces us to deal with a fundamental aspect of the 'cinema of loneliness' that Kolker intentionally sidesteps: the use of preexisting popular music to offer a glimpse into a character's state of mind. Moving beyond the confines of film and narrative theory, and situating the film in broader histories of listening, cinema-going and audio technologies, I argue that the soundtrack of The Graduate reflected new ways of listening 'alone together' that were developing both within and without the cinema theatre. I show that the film employs music in a manner consistent with how transistor radios were being used and discussed in 1960s America, and I explore how – in the very process of placing loneliness at the centre of its audio-visual aesthetics – it enabled heavily mediated experiences of shared loneliness. More specifically, I propose that 'The Sound of Silence' is central not only to how The Graduate conveys loneliness but also to how the film provides a provisional and non-political way out of it.