setting iTunes to sync random selections

It's not the best solution, but I have the same problem so I made a Smart Playlist that has a random 2GB of music. It only updates once though, so each time I want a different selection I add a new parameter that throws the playlist out of whack, and then remove the parameter. This forces it to re-update. 🙂

You have two choices:

Firstly as madjew says create a smart playlists that fills with 10 gigs of random music. Then visit Dougs Scripts and find the 'Reshuffle Smart Playlists' script. This will reshuffle the music, so do that every day and it will repopulate with random stuff.

Other than that you can use a freeware app called The Filter - http://www.thefilter.com - this app can make automatic lists that fill your ipod and refresh with new songs everytime i connects. Give this a try and create a few of these playlists, probably a bit healthier than filling it totally randomly.

Rasheem said:

So im stuck with my 10gig 3rd gen iPod. Unfortunatley I have way more music than 10 gigs. So how do i set my itunes to randomly pick a new selection of music everytime i plug my ipod in and sync that selection to my iPod?

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Another thing you could do is to create a smart playlist that consists of all songs you have not played in the last (30/60/90) days. It won't give you an entirely new iPod full of music, but it will remove all the songs you listened to the last time you synced and put new ones on there. Basically the same thing (does a song on an iPod count as a song if you don't listen to it?)