Where are you downlaoding all these copies from? The same place each time (possibly Kazaa)?

I remember something about it's possible to create corrupt ID3 tags in MP3s that cause programs to crash when they read them - Winamp posted a fix for that back in December, and I know there was a patch for Windows too, which was Q329390. The security page with links to patches is here. Maybe try installing this patch first, then see if you can select the file afterwards.