In accordance with some embodiments, a method includes displaying a representation of a first automatically-generated playlist, the representation of the first automatically-generated playlist including representations of a first set of media items selected for inclusion in the first automatically-generated playlist based on first playlist generation criteria for the first automatically-generated playlist. While displaying the first automatically-generated playlist, detecting user interaction with the representations of the first set of media items, and then detecting that a first update criterion for the first automatically-generated playlist has been met. In response, the method includes updating the first set of media items based on the first playlist generation criteria and the user interaction with the representations of the first set of media items—by adding or removing one or more removed media items from the first set of media items, and/or maintaining media items in the first set of media items.