07-29-2009, 11:08 PM
Create a smart playlist in iTunes.
Uncheck the box for "Matching".
Check off the box for Limit to: [xx GB] selected by [random].
Tell the iPod to sync that new smart playlist.
That would be totally random. You can also create multiple smaller smart playlists and use various matching criteria to give the playlist some direction without a lot of work. Like a playlist of songs with 5-star ratings that have not been played in the last month, or whatever.
Uncheck the box for "Matching".
Check off the box for Limit to: [xx GB] selected by [random].
Tell the iPod to sync that new smart playlist.
That would be totally random. You can also create multiple smaller smart playlists and use various matching criteria to give the playlist some direction without a lot of work. Like a playlist of songs with 5-star ratings that have not been played in the last month, or whatever.