#1: Hundreds of non-itunes songs no longer play on laptop or iPod Touch! #2: How to recover music from a broken laptop to put it on my new one?

Old problem that has never been figured out: I had hundreds of songs on my old laptop before itunes, some of them downloads from years ago and some of them ripped from CDs. After getting an ipod touch a few years ago, I put all 900 and some of the old songs plus new ones purchased from itunes on the ipod and played them for a long time (year or 2 probably?). Now, all of the sudden the non-itunes songs are grey on my computer AND ipod, and I am not able to click on them or play them. Why is this?
New problem that I will be severely p1ssed off about if it can't be resolved: Previously mentioned laptop with all of the music on it stopped working, so I purchased a new laptop and now, the only songs that show up in my newly downloaded itunes are the purchased ones. No music from old downloads, no music from CD's, and no playlists created on my old computer. Only a list of the songs that I purchased directly from itunes. I no longer have all the CD's that funded my 950+ song collection and have no way of getting that music (or the downloaded music) back if I can't access the broken laptop. What do I do now?!

SOLUTION: circle with red square Some Music Won't Play After...: Apple Support Communities

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