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You need a music converter the music files are most likly not .mp3 or .mp4 files thay are most likly .wav files and some pods cannot play this type of music, You can use windows media player to convert them for free then reload them onto your pod.
Search convert music using medial player and you will find direction on how to do this.
This may not be the answer you are looking for but your I pod might not be fully charged, meaning that you are not plugging it in the computer/docking system long enough.( it takes much longer than 15 minutes to charge the battery. So you might want to plug it in/dock it over night) Or you may be playing a game that uses a lot of MB/GB so it kills the battery. And make sure that you press the play/pause button down for at least five seconds before switching the little switch at the top of your I pod. If you don't press the play/pause button for five seconds and just switch the switch at the top a little lock will appear on the left corner meaning you need to hold the play/pause button down for five seconds then the i pod screen goes black at that time flick the switch at the top off.
-hope it helps
owner of i pod nano and I pod touch.
Check that when you plug your iPod in that it isn't selected to "Shuffle," play which can happen if you are expecting to go through songs. There is also another reason and one I didnt know about until I took my iPod Classic back to my retailer thinking there was a problem;
If the songs on your iTunes or default device isn't an AAC file the iPod will fail to play it. On MAC systems simply click the file that you want to put onto your iPod, right click and scroll to "Get Info." If the file doesn't say it is an AAC file it won't play on your iPod. Scroll further down on the list to "Create AAC version." This takes milliseconds, doesn't affect the sound quality but condenses the data fit for the iPod Classic. Once that's done you can add any song you like.
Generally when you put a CD into a MAC it will automatically change the AIFF files into AAC which means you don't need to manually convert. AAC is usually needed when individual tracks are called up and put onto your iPod. I hope this helps you - it drove me nuts until I found out about the AAC.
You need to set your iPod to update manually, instead of syncing automatically when you plug it into the computer.
To do this, plug your iPod into your computer, and on the iPod info screen that pops up in iTunes when your iPod is connected, click "Manually Manage Files." You'll now have to click and drag your songs from your library to your iPod, but now you can also play songs on your computer directly from your iPod and delete songs from your library without deleting them from your iPod at the same time.