Fifth Generation iPod won't play anything purchased from iTunes!

My 30GB iPod video will not play anything that I have purchased from iTunes.
I just got it last week and this is really frustrating.
I got "Dave Chappelle: For What It's Worth" and the album "Liquid Swords" by Genius/GZA. The video and all the songs play fine in iTunes but my iPod skips through the songs not playing anything and when I try to play the video it goes black like it's going to start playing but then it just goes back to the menu.
I have looked through the support page and have tried de-authorizing and reauthorizing my computer, updating my iPod (it was up-to-date), restoring my iPod, removing the files from my iPod and putting them back on, re-installing iPod updater, running repair on iTunes, recreating your iTunes library, resetting my iPod, and even tried using a different USB port. All of which produced the same results as before.
If anybody could help me out here it would be greatly appreciated. I can’t believe it is this difficult to get files from iTunes to an iPod, aren’t these supposed to go hand-in-hand?!?
Dell w/ Pentium 4 CPU 2.80GHz and 512 MB of RAM Windows XP

Welcome to Apple Discussions!
First set of steps (These are general instructions. You may have tried some)...
Try playing the song in iTunes for a few seconds, then sync the iPod. Does it work?
Also, in iTunes go to advanced-->deauthorize computer. Now play the song. Type in your iTunes account information and password. Play a few song you have purchased for a few seconds each.
Sync the iPod. Do they work?
Also, make sure everything is up to date...
iPod Updater
iTunes
btabz

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See this article.
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See this: iPod does not play content purchased from the iTMS.
If you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, try this test:
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Fifth Generation iPod won't play anything purchased from iTunes!

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