ITunes music will play on iTunes but will not play in my iPod

I downloaded music from iTunes. It plays on my computer and shows up on my iPod. However, it will not play. When I attempt to play the iPod says "now playing" skipping all 25 tracks. The music is in the purchased, artist, music, etc. folders.
Any thoughts?
G4   Mac OS X (10.4.3)  

You will be able to post a new topic in almost every Forum (not a Category)
E.g, click on Forum: Using iTunes for Mac and you will see a 'Post New Topic' icon at about top left of the window.
Use the 'Add to Library...' option from the File menu and navigate to the DVD.
Be sure to tick the checkbox ' Copy files to.....etc.' in Preferences>Advanced>General.
M
17' iMac fp 800 MHz 768 MB RAM   Mac OS X (10.3.9)   Several ext. HD (backup and data)

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