AppleScript for iTunes
Four iPod Scripts X v1.0
Obligatory warning: This script has been designated as an obsoleted "Retro Script". There is no guarantee that it will function as described with modern versions of iTunes (or the newer Music or TV apps) and/or macOS. If used in its current form it may not work at all without modification. At worst, it may corrupt or delete data.
These five scripts work nicely together, OS X only:
Random Albums to iPod deletes all songs and playlists on your iPod, selects albums at random from the iTunes Library and adds every song on those albums to your iPod until it is full.
Random Artist to iPod deletes all songs and playlists on your iPod, selects artists at random from the iTunes Library and adds every song by those artists to your iPod until it is full.
Random iPod deletes all songs and playlists on your iPod, selects tracks at random from the iTunes Library and adds then to your iPod until it is full.
Random Playlist Tracks to iPod deletes all songs and playlists on your iPod, selects tracks at random from the a playlist you've selected and adds songs to your iPod until it is full.
Clean iPod deletes all songs and playlists from the iPod.
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