A system can receive and/or otherwise access information about items of content (e.g., audio tracks, video tracks, images and/or other items), information about a playlist to be generated, information about the past behavior of the target entity for the playlist and/or information about the past behavior of other entities. Examples of information about the items of content include genre, artist, album, time period, etc. Examples of information about a playlist include tempo curve, event type, playlist duration, etc. Based on all or a subset of the above-described information, the system automatically generates a playlist that identifies items of content. The playlist is presented to the target entity so that the target entity can acquire the playlist and/or the items of content identified in the playlist. In some embodiments, the target entity is also provided with an opportunity to edit the playlist.