Random Playlist Creator for Mac

From Software on the Side:

Random Playlist Creator is an application that randomly generates iTunes playlists from a source playlist, which can be of any type that references Library tracks.

Features

• Creates multiple iTunes playlists of a specified combined file size or playing time.
• Creates "super-playlists", each consisting of one or more segments (each segment comprises an iTunes playlist). This feature is especially useful for flash-based MP3 players with expansion cards where the internal memory is a different size than the expansion memory.
• Allows the last generated super-playlist to be randomly padded with tracks from previously generated super-playlists.
• Allows groups of tracks to be kept together in a specified order within the generated playlists.
• Track groupings can be defined either by creating a specially-named playlist or by defining the "grouping" ID3 tag in each song file.
• The defined track groupings can be individually enabled or disabled for use when generating random playlists with the track grouping option enabled.
• Provides an enhanced shuffle mode where an entire playlist can be shuffled into a single new playlist with the track groupings intact.
• Includes an option to use only the MP3-formatted files in the source playlist -- useful for MP3 CDs and non-iPod MP3 players.
• New: Supports user-defined presets for often-used settings.