IPod won't play purchased music from iTunes Store

My iPod won't play purchased songs from the iTunes Store. They play on my computer, using iTunes, through the iPod, but my iPod won't play the songs with headphones, or in my BOSE speaker station, nor in my car using my Belker radio adapter. I've purchased a few songs before, and haven't had this problem. I wasn't prompted, as I have been before, to enter in a password before playing the songs.

i have the same problem, and i looks like there are another 4 or 5 discussion threads with the same prob. my ipod is about 14months old, got one of the first 4th generations when they came out -- have never had a problem, then when i downloaded itunes 6, all of a sudden everything i have purchased since then plays fine on my computer and just keeps scrolling thru and not playing on my ipod. very very frustrating. i have tried everything, right down to a complete restore on it, and nothing helps. also, when i downloaded itunes6, my purchased music playlist disapeared -- i spent 2 weeks and 5 emails going back and forth with tech support because they wouldn't address the issue, and am wary of going to them with this one. i thought the drive or memory on the ipod was corrupted and was going to buy another one, but now i'm not so sure -- is anyone having this issue with a 5th generation? because what it looks like is itunes 6 downloads may not be compatible with 4th G, and that makes me a little cranky. any one find a solution for this yet?
hp pavilion   Windows XP  

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