Help - Cannot play music purchased from iTunes store

HI,
Hoping someone can help me. I cannot play any music I have purchased from the iTunes store on my Macbook Pro or iMac at home however I can play the tracks on my iMac at work. This occurred after I reinstalled Leopard on my main iMac at home. Here are the steps I have taken so far to try and resolve:
1 - Deauthorized all computers
2 - Reauthorized all computers
I recently copied the music library from my home iMac to the work iMac and laptop they are all the same files now, not different versions. Essentially I'm playing the same file on each machine and all machines are authorized.
If I select a purchased song at home or on my MacBook Pro, a window opens saying I am not authorized, blah blah blah. I input my details which I know are correct. The message tells me the authorization was successful but if I click on the song, the window opens again telling me I'm not authorized - ARRRGHHH!!
BUT the weird thing is, the files all play on my work iMac. This is the only device that hasn't changed recently - the home Mac is a new OS restore and the MacBook Pro is about 2 months old, but if I've authorized them I don't understand why they won't play.
Trying to contact iTunes support it impossible so I thought I'd see if anyone else has suffered a similar experience?

I have the SAME problem and it's driving me INSANE!! I contacted an iTunes person and she's trying to help me but it didn't really help much... The stupid authorization prompt won't stopp popping up and I'm about to throw my computer out the window... It will sync and everything, but before it's done it will say some of my songs weren't copied to my iPhone because I'm not authorized, even though I AM. It's highly depressing... I really want to fix this problem. I thought it was just my computer because if just recovered from a major virus that we fixed, but what you explained is Identical to my problem. If you find a solution, please tell me! Thank you very much.

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https://discussions.apple.com/message/24380694#24380694
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Welcome to Apple Support Communities!
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FAQ: Why iTunes Match Can Not Be Used as a Backup - https://discussions.apple.com/docs/DOC-4112
Using Match as a backup for iTunes - https://discussions.apple.com/message/17039436#17039436
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Help - Cannot play music purchased from iTunes store

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