Method and apparatus for programmatically generating interesting audio file playlists. A playlist generation mechanism may use an N-gram model of audio file ordering patterns found in a collection of human-generated playlists to automatically generate new playlists. Given play histories indicating one or more played audio files as input, statistical methods may be used to look for sequences of audio files that occur a statistically significant number of times in the N-gram model for inclusion in new, interesting playlists that incorporate the human element found in the collection of playlists. In some embodiments, one more backoff probability methods may be used to provide additional candidate audio files for playlists if there is insufficient coverage for an audio file in the N-gram model. In one embodiment, a class-based statistical model incorporating higher-level statistics for the audio files may be used to weight selection of audio file transitions from the N-gram model.