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Possible that the files have been saved inthe wrong way. If you have them again in the PC , delete off all the files you had sent, format th device or erase off all files, scan for any virus in the device before loading back the music files with the PROPER METHOD OF COPY AND SAVE, USE THE RECOGNISED PROGRAM for the ipod- the ones the songs are playing presently. Helpful? good day
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.
Try converting the songs into a different format because the format that the song is in might not completely be played on the ipod. Right click on the song and click on convert to mp3. Then try transferring the mp3 format song onto the ipod and it should play right then.
Try resetting your ipod by holding down the menu and select (round button in the center) buttons down for at least 10 seconds. You'll see an apple logo flash, that's when you stop pressing the buttons. It will shut off, then back on.