A sequential playback system is configured to select each sequential song based upon characteristics of an ending segment of each preceding song. Songs are selected based on the characteristics of the overall theme of the selection, if any, and also based on a musical correspondence between songs. The correspondence may be based on the rhythm of each song, the notes and chords of each song, and other musical characteristics of the songs. The end segment of each selected song is characterized, and the first segment of a candidate song that satisfy the overall selection criteria is compared to this characterization to determine a correspondence. If the first segment of the candidate song is inconsistent with the end segment of the previously selected song, another candidate song is found that satisfies the overall selection criteria, and the first segment of this new candidate song is compared to the characterization. This process continues until a suitable candidate song is identified, or until a time limit is exceeded. Transition pieces are optionally provided to facilitate a smooth transition between songs.