How to randomly fill songs to ipod/itouch

Question

I would like iTune to randomly fill songs to my iTouch like the IPOD Shuffle. My problem is if I checked the option to automatically fill songs to my iTouch, it always update with the same songs and that is the same 400 songs out of my over 2000 collection.

Answer 1

Okay.
Just for information though (and for the benefit of other readers), the basic idea is create a Smart Playlist (a controlling Playlist) that includes the music you want to remove temporarily. So the first rule would be (for example) Genre / is / pop. The second rule is Last Played / is not in the last / 3 months for example. After a song is played, it is removed from that Playlist for a period of three months. After that, it is automatically put back into the Playlist again.
If you Sync only selected Playlists and choose that (controlling) Smart Playlist, then the contents of the Playlist will be the only music on your iPod. (When choosing these options - with the iPod connected and you looking on the iPod/Music pane, you can specifically Sync particular artists, albums etc. So any album for example can be made to stay on the iPod all the time, in spite of the controlling Playlist rules.)
Note though; if the music is recently added to iTunes, it will be in the Recently Added Smart Playlist. If you allow the Recently Added Playlist to Sync with your iPod, then the songs will stay on the iPod because they are also in the Recently Added Playlist.
Likewise, (and more importantly), after being played, songs are added to the Recently Played Playlist. If that Playlist is allowed to Sync with your iPod, then once again the songs will stay on the iPod. This could be a good thing; the Recently Played time is two weeks. So once a song has been played, it will stay on the iPod for two weeks, so if you feel like playing a song several times in a short pereiod, it will still be on the iPod. But after two weeks, it it hasn't been played, it's dropped from the Recently Played Playlist as well, and therefore removed from the iPod. With your controlling Smart Playlist set at three months, the songs will be removed from the iPod for 10 weeks.
If a song stays on your iPod when you don't expect it to, then there will be a Playlist somewhere that's causing that. You simply have to find it and modify the rules to make it do what you want.
If this method doesn't remove enough songs from the iPod, simply lengthen the exlcusion time to four, five or more months. You can also reduce the Recently Played time if you wish. Or exclude more songs; you can do this by genre or even by time.
A slightly rushed explanantion. If you need more help, ask.