IPod keeps scrolling thru "purchased" list; can't play ANY purchased iTunes

I run into this problem every time I purchase iTunes. I go to play a song from the "purchased" folder and my iPod just scrolls through the whole list and will not play any songs. I have to update my iPod to straighten the problem out. Then if I recharge it the problem starts up again. HELP, THIS IS DRIVING ME CRAZY!!!!!
iPod 20GB   Windows 2000  

This is what you need to read then:
http://docs.info.apple.com/article.html?artnum=303854
Rachyl

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