Playlist order not updating!

I have been using my iPod Shuffle for several months to listen to podcasts, among other things. I know how to drag files in the playlist so I know what will play first.
For some reason now, the playlist shown in iTunes (6.01) is NOT reflected on my iPod. This is driving me NUTS! I have tried restoring my iPod several times. After all files are copied back to the iPod, they play in some other order than the order shown in iTunes.
I know how it's SUPPOSED to work. As I said, I have been using it to listen to podcasts for several months.
Could there be a corrupt file on my system? I have had a system freeze. I have run scandisk and updated iTunes. Should I rebuild my library? What would be the easiest way to do that?
Thanks,
Tim

Hi Tim,
Take a look at this thread which covers this issue and explains how to set the play order:
http://discussions.info.apple.com/webx?128@@.68bcfa2b
Also, jmurray is right, podcasts always play first.
Hope that helps,
Sara.

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