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The 5 R's for Apple iPods – www.apple.com/support These are for Nano, but they apply to all iPods: Reset, Retry, Restart, Reinstall, Restore Remember these five basic suggestions if you have a problem with your iPod Nano. If one of the following doesn’t help, read on for solutions to specific problems. - Reset your iPod Nano. See “General Suggestions,” below. - Retry with a different USB port if you cannot see iPod Nano in iTunes. - Restart your computer and make sure you have the latest software updates installed. - Reinstall iPod and iTunes software from the latest versions on the web. - Restore your iPod Nano. See “Updating and Restoring iPod Software” on page whatever. -Tha Mp3 Doctor
You can get the files from an online music service like iTunes, Napster, Rhapsody, Limewire, Bearshare, etc. Or you can use Windows Media Player 10 or 11 to "Rip" songs from a CD - I would reccommend ripping them in mp3 format.