Some Songs Will Not Play Even After Being Authorized

Just this past weekend, I had to reinstall Tiger and then upgrade to Leopard due to a “kernel panic” that would not go away no matter what was tried. As such, iTunes was started from scratch. Unfortunately, I could not locate my iTunes library within the Previous System folder after this reinstall. In all honesty, I probably just didn’t know where to look.
So, I transferred my music from my iPod to my iMac. But, some of my songs will no longer play. The songs that will not play are songs that I purchased and downloaded from iTunes. However, the recent songs purchased and downloaded will play…it’s songs that were purchased and downloaded a few months ago. Strange.
When I click these songs a box pops up for me to authorize it. I do so and it says that this computer is already authorized. I click on the song again and the same thing repeats itself.
I have two accounts that I have used. I have both accounts authorized on this computer. I have restarted with no success. I have unauthorized and reauthorized with no success. I’m afraid to sync my iPod in case these same characteristics transfer to my iPod.
I have not updated Leopard to the latest version as of yet since I just reinstalled from the disc orginally sent with my iMac. Any help is greatly appreciated as I’m out of ideas…

I had the exact same problem today. Two days ago I let Software Update auto-install Security Update 2008-008 (Client Intel) on my machine. I was rewarded with the gray screen and spinning wheel that never went away, and after hours of fruitless attempts to resolve the problem with Disk Utility and Terminal, I was forced to Archive and Restore to 10.4.8 and then rebuild my system back to 10.4.11.
I thought everything was fine after that until I went to play my iTunes music tonight. Though I'd had no problem playing music ripped from CDs, anything that I'd bought from the iTunes store wouldn't play -- it gave me the exact same error that you reported. I've followed all of Apple's troubleshooting steps -- repairing disk permissions, deleting the SC Info folder, etc., and nothing worked. I spent nearly an hour online with iTunes Chat Support and they say that my account tests fine on their end, so it's not iTunes -- something must have happened to my machine.
Personally, I think it was Security Update 2008-008. It's been nothing but trouble.
Now I have to pay $50 for a phone call to Apple Tech Support. Lucky me.

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