This is directed to selecting and associating media playback settings with playlists. A user may create a playlist from a library of media items, and associate one or more selected media playback settings with the playlist. The media playback items can include audio, image, and video files, for example, and the media playback settings can include, for example, cross-fading properties, volume properties, equalizer settings, sequential playback settings, and the like. When the user selects a playlist for playback, the media items of the playlist may be played back according to the media playback settings associated with the playlist.