IPod Nano 3rd generation: Only plays songs recently downloaded to my iTunes Library

iPod Nano 3rd generation (Version 1.1.3) for Windows
Any song that I download onto the iPod shows up in its library, but when I try to listen to the songs, they won't play.
The only songs the iPod will play are those that have just recently downloaded onto my iTunes library.
If the new songs aren't on the iPod, then when I try to play a song, the "now playing" screen shows up, not showing any songs, and the playlist says "playing 1 of 0"

Hi LeviBC,
It sounds quite frustrating having your iPod only play certain songs, I am quite sure I would be unhappy in similar circumstances. Let's see if we can get you up and running.
If you are having issues with your iPod nano (3rd generation) not playing some of your music, I would suggest troubleshooting using the steps found on this page -
iPod - iPod nano (3rd generation) Troubleshooting
http://www.apple.com/support/ipod/five_rs/nano3gen/
Thanks for using Apple Support Communities.
Best,
Brett L

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