Songs Won't Load on New Ipod

Got a new Ipod because my old one died. I can't load songs onto it. Here is what happens. When I hook the Ipod up, Itunes sees it and attempts to load the songs. I get a message that says it can't copy some of the songs because they aren't playable on this Ipod. This never happend with the old Ipod. I hit OK. Then I get an error that says "Attempting to copy the disk GREG's IPOD failed. An unknown error occurred (-69)." Any ideas?

This did help. However, I had to delete the file and just not uncheck it. I changed the preference to download only checked files, but it tried to download it anyway. Any idea why that would happen? Additionally, the "corrupt" file was a podcast. Are podcasets more apt to be "corrupted." This is the first that I have ever used my ipod with podcasts, and I am trying to understand if I should expect more of thest types of problems.
Thanks so much for your help.
Greg

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Hello all!
I just got an 80GB ipod and have already added thousands of mp3's to iTunes. Now I have hooked up the ipod to sync and after SLOWLY updating 2 or 3 songs the error message says:
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Make sure your Windows software is up-to-date ;That you have all the recent updates.
Make sure your running the correct software version for your IPOD;
In your case it has to be ITunes Version 7.0 or higher.
Make sure your battery is okay or Charged.
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Menu and Center simultaneously, for about 6 seconds.
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These five steps (known as the five Rs) will conquer most iPod issues.
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2. Retry with a different USB port.
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5. Restore your iPod.
as you may want to get more answers, before returing unit.
If you have a computer system problem then you'll have the same problem with the new unit.
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http://support.apple.com/kb/ht1320
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From: Apple Support Communities Updates
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Sent: Monday, February 27, 2012 3:40 PM
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Subject: - Re: I want to install the latest version of
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I have a bizarre problem.
All of my songs that are on my iPod are in iTunes (How else would they get on my iPod xP) and they all work fine. In general, the songs on my iPod work/play fine, minus a few.
When I go to play them, the load up, I see everything that should be there (album cover, band name, song name etc.) but the song doesn't play. What does happen though, is that the iPod rapidly goes through the album, going song to song, without playing any of them, as if I were pressing the skip song button. (which I am not pressing)
Then it slows down and stays on one song, staying at the 0:00 mark, even though the play arrow at the top is there. If I press pause and then play again, the arrow icon changes, but the song still won't play.
Now if I go to any other song by any other band the iPod won't play that song. If I press the center button, and move what part of the song it is at, it skips to the next song, and it doesn't matter how far into the song I put it. It's like the screen shows there is 4:24(or any time, this is just an example) of a song but the iPod thinks there is 0:00.
A simple restart of the iPod sets everything back to normal, I can listen to my other music without a problem, but the same thing happens when I select any of those songs.
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i have this exact problem on my 120 classic. it started earlier today on a few song i had downlaoded from the iTunes store. i thought it was an accessability issue since i had just updated to the latest iTunes, but it started happening on my songs from CDs, and then what you described happened on every single song i played on shuffle (out of about 10,000 songs total)
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Songs Won't Load on New Ipod

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