How to transfer music from old hard drive

I just upgraded my drive (same computer) and installed leopard. My older drive has my imported and purchased music on it. Running under Tiger. I can access the drive with a remote kit, so all files from the old drive are still accessable.
how and what do I need to do to transfer all my music library and purchased music/authorizations to the new hard drive?

I've tried doing that, and had an odd result. All of the names of the songs are added to my library, but when I attempt to listen to well over half of them, I get an error message:
"The song "__" could not be used because it could not be found. Would you like to locate it"
And indeed, the only music that shows up in the finder window are songs that will play. The very newest music seems to play, including things purchased from iTunes. Tech support said they can't help with the issue because of copyright concerns, but I just don't want to put 5 crates full of CDs into my computer one by one!
Any thoughts?

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