Can't play songs due to old Apple ID / Can't authorize music

I have this really ANNOYING problem where, since I went and got a .mac account and have a new Apple ID, I can't access some songs I bought a couple years ago with my former Apple ID. ITunes keeps asking me to authorize the content, brings up a window with my old ID, I enter the password and it seems to work -- but it doesn't. Every time I try to play the song, it brings the window back up... it's an endless loops and I can't access the songs!
What is the answer, Apple? Can you not correlate older and newer Apple IDs? Why can't I authorize the music with the old ID if I remember the password? Because the account no longer exists? If that's the case, my music is literally being held hostage without any known recourse. Please advise

kidsbesides74 I am with you there man, I know I sound like the usual Mac poster, but yes I have been a Mac head forever and have had every iPod/iTunes since the first, but I am STUCK, I have tried all these suggestions, but I can not get the bulk of my iTunes collection, ( 2000 of over 4000) songs to play because of the same problem, It just says that this Apple ID does not exist even though I can see it right there in the >Get Info for each of these songs. I will have to call Apple directly in the morning, I just hope they don't do that thing where they say that I must be doing something wrong. Is there a limit of two Apple ID's , I now have two Apple ID's here at the house and a third at the office could that be the problem ? if so, how do I get the songs I paid for folded into my other account?

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