A recent development in literature’s engagement with music involves the role played by emerging technologies and the way they not only transmit musical content to the listener, but very strongly condition the form the music takes and the way we listen. While music is still often considered ephemeral and transcendent, there is a new recognition of it as an object and a commodity, whether an LP record or a file to be downloaded from itunes. Technologies coexist; records are now collected and venerated in a nostalgic mode while music moves into the digital sphere of downloads and participatory cultures of online sharing. Contemporary literature can tell us not only about the idealization of music as a non-referential and thus “higher” art, but about the way music is mediated by technologies. The present paper focuses on two recent musical novels that foreground the mass media of musical expression, Nick Hornby’s High Fidelity (1995) and Arthur Phillips’s The Song Is You (2009). Both celebrate songs — incorporated as records in the former and digital files on an ipod in the latter — as symbols of taste, carriers of memory, means of establishing interpersonal connections, and media that condition our thinking. Songs also exist in relation to others, demonstrated by the protagonist’s fixation on lists modeled on radio’s top-forty rankings in High Fidelity and on juxtaposition of songs on the ipod’s shuffle mode in The Song Is You. The comparison of these novels in terms of their focus on different musical technologies leads to an exploration of modes of listening as characters experience their lives through the lens of popular music.