I have an iPod Classic from 2007 (Generation 5.5, 80GB hard drive).
Something that I've been noticing happening more and more is that some songs will play just fine but then at some point they'll just stop. The little time counter will jump to where it appears there is two seconds left in the song. And it will just sit there for several seconds and then then proceed to the next song.
And what I've noticed is that it tends to happen consistently with the songs that are problematic.
I've searched all over to figure out what might be causing this but I haven't had much lock, possibly because the symptoms are so vague ("some songs cut off", etc.)
My music collection, which is always pretty much filling the device, is 100% MP3 from a wide variety of sources (ripped, bought from Napster, etc.) and everything plays fine in Winamp on my PC so it doesn't seem as if the files themselves are completely corrupted.
My guess is that there is something about the files that the iPod is choking on but I can't figure out what that might be. If I'm lucky it's some weird tagging quirk (i.e., can be fixed in the individual files) but I really just don't know, and it seems to be happening on an increasing number of files, including files that played just fine before. Sometimes an entire album or artist will consist of files that cut off.
If this is just some known issue, do the latest iPod Classics (Generation 6, 160GB hard drives) still have this issue? I'm almost hoping that this is a sign of a dying iPod so I can upgrade :)