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.
What's new in Random Playlist Creator
Version 2.2: Added support for user-defined presets for often used settings.
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Create new smart playlist. Under the settings for that playlist say taht the songs must be from another playlist or library. Then say select number of songs randomly. Ta-da! All from within itunes!