Unable to play tracks on I tunes

When I go into my I Tunes and click on an Album/Track and try to play it, a window pops up stating " The song'............' could not be used because the original file could not be found. Would you like to locate it? If I click on 'Locate It' nothing is found! The only tracks I can play are those that I have recently uploaded from CD's into I tunes and that have not yet been synced with my I Pod Classic.
My I tunes library is stored on an external hard drive and I have not upgraded my I tones software to the latest version since originally installing I tunes some years ago

I'm experiencing that issue in this very moment, and it's killing me! It's a couple of specific albums and songs that are doing this thing on my iPod and after I've tried to play the song it skips and keep on skipping until it comes to a song it will play. Jugding on the sounds of my iPod during this terrible incident I believe we're dealing with a loose connection within the iPod. I believe that I by an accident have dropped it a couple of days ago, and my iPod sounds like everytime it tries to play the songs it's crashing. I then tried to lay down some lyrics on the specific songs and paused them so that I could see the lyrics, but as I tried that it said lyrics were found, but unable to read it or something like that. I think we need to send in our iPods, hope you have an assurance.
If someone's got another idea or solution, you are very VERY welcome to drop it

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