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 (Library, normal, smart, Purchased Songs, Party Mix are the types that come to mind). It requires that iTunes is running: when run, it will start iTunes if necessary and will automatically quit if iTunes quits.
Version 2.2: Added support for user-defined presets for often used settings.
Mac OS X 10.2.8 or later, Tested with iTunes 4.6 but should work with any version that runs on your OS X version.
*Previously available here