Multiple playlists can be generated for broadcast or streaming. An aggregate difference representing a difference between the aggregate playout length of the multiple playlists and a target playout length can be determined. If the aggregate difference exceeds a difference threshold, a subsequent time period can be reduced, so a playlist generated for the subsequent time period can be constrained to be shorter. The playlists can be generated based on different versions of a ranking chart or list that includes ranked media items, e.g. songs, videos, etc., by automatically including the highest ranked media items to the playlist, but only adding some of the lower ranked media items to the playlist. Lower-ranked media items can be pseudo-randomly excluded from one or more of the playlists if the media item's rank in a newer version of a ranking chart is lower than its ranking in a previous version.