Purchased music will no longer play on iPod only

Has anyone else had this problem with iTunes 6? None of my purchased music wil play on my iPod anymore, I have updated to the latest versions of all the software, iTunes, iPod and QuickTime. I bought music today. As soon as I copied it to my iPod, not only will the new music not play, but nothing I have purchased from iTunes will play anymore. The device simply skips to the next song on the list not from iTunes. No messages or explanation. It simply ignores the files and moves on to the next. All music plays on my computer. This seems to be an iPod problem, and there are no updates to add for it. It only happened after I upgraded to and purchased music from iTunes 6, Any ideas? All suggestions would be appreciated.

Thank you for responding. I am using iPod software 2.3 on what I believe is a second generation 15GB iPod, the one with the four buttons below thw screen; the last one before the click wheel version. I think it's the only one they made in 15GB size. Anyway, 2.3 is the most updated software that this model can take. I've noticed from the discussions that many people are having similar problems that vary a bit. I hope Apple is noticing these glitches.

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