During the early 1980s, a number of medley records achieved considerable success on pop singles charts. Judged by the standards of today's mash-ups and mix-CD compilations, these records may sound clumsy: the medleys often lurch from one song to the next with little overlap between songs. However, the same medley records have often been described as seamless. This article explains how medley producers created an impression of seamlessness, with particular attention to two 1981 hits: Stars on 45 and Hooked on Classics. The arrangers of these records used several devices to convey an impression of seamlessness, such as pivot notes, harmonic modulations, and the overlapping of similar timbres across different songs. The analysis demonstrates three points. Firstly, notions of seamless segues have shifted significantly since the disco era. Records such as Stars on 45 and Hooked on Classics exemplify earlier types of segues, in which arrangers move quickly from one song to the next, exploiting existing similarities between song fragments. Secondly, medleys of popular music meticulously replicate their source material, while medleys of art music tend to alter their source material. This can be attributed to popular music's phonographic tradition, in which a recording (rather than a score) counts as the work itself. Finally, we can learn much about listening itself by attending to these records. Medley records make sense when approached with a mode of listening suggested by Jerrold Levinson, an approach where moment-to-moment transitions matter more than large-scale structure or cohesion.