A very strange issue with my Ipod Classic

Hello everyone
Well I have a Ipod Classic 160gb
all this time I was using it and was so flawlessly,
but 4 days ago, suddenly when I connect the Ipod into Itunes and listened some songs for a while, I go to the Ipod in the windows explorer, open it and then happened, my Itunes stop playing songs and show a error when it tried to play songs (is like they were deleted), so I go to check the Ipod in windows and for my surprise when I tried to get into the Itunes folder appeared a error message saying "Insert Disc In Unit I:\" (this happen with all my others folders inside the ipod), so I look at the properties and showed me that I had 90GB used and 58GB free, then I decided disconnect the Ipod and see if it plays songs well or if it's corrupted.
Since then the Ipod plays songs so badly, don't play some songs skips another ones, got freeze, and every time I plug it into a PC I can't see my folders inside the Ipod, but is able to plays songs perfectly in Itunes, provided i don't open the Ipod in Windows Explorer.
I need recover about 50gb of data of the Ipod (not the music)
but in the worse of the cases I want my Ipod play the songs well, (I already tried to restore but always have an error)
Please Help me I think the data still is ok but i don't know what to do, I don't wanna lose it.
(Note: I always connect the ipod in disk mode).
PS: Sorry about my bad english.

When you connect the iPod in Disk Mode, it will be a external hardisk to Windows. So if the iPod filesystem is corrupted due to a dying hardisk, you may get missing folder in WinExplorer or some strange behavior.
Do the iPod Disk Diagnostic as posted by tt2, it wont fix your problem, but help in troubleshooting.
Why do you need to connect in Disk Mode and play songs in Windows Explorer? Dont your iTunes library have those songs?

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