Certain files won't play properly

I've never had this problem in the past but recently (in the past month or so) certain songs in my library will play properly up until a certain point and then just stop and give me the beach ball. Pnce that happens I can't do anything on my computer until I force iTunes to quit. I've tried installing the newest upgrade and it hasn't helped. Any idea what's wrong?

P.S. I just tried playing some of these files on other media players and encountered the same problem. At a certain point in the track the program stops responding entirely. It's even been known to happen to files that I've just added. Also, I keep my library on an external drive and it's accidentally been unplugged while playing once or twice (though the songs that were playing at the time aren't the ones that are problematic).
P.P.S. I tried to create an AAC version of one of the files just now and it gave me an error message (-3). Hope that can give more insight into the issue.

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