My MP3s cannot be played on this iPod?

I just bought the newest-generation red 16GB iPod. I have a song that was NOT purchased in iTunes but that PLAYS in iTune, and which "was not copied to the ipod because it cannot be played on this ipod."
The song is an unprotected 160 kbps 44.100 kHz MP3 file--looking quickly I cannot tell in iTunes if it's variable rate.
I read some other forum questions and tried re-creating my iTunes library (http://support.apple.com/kb/HT1451) to no avail. I've also seen suggestions for converting the file format--especially when it comes to video, but also for some reason when it comes to MP3s. A) This seems silly, especially in light of the fact that B) the only option I seem to have is Apple Lossless, rather silly considering I'm converting from the lossiest of file formats.
To reiterate--this music was NOT bought in iTunes, then burnt and imported. This is a regular old (and I mean old) MP3 (MPEG-1, Layer 3) audio file.
Any help in keeping my temper in check and chucking my now largely useless iPod (it's happening with a LOT of the music I want to import) out the window would be MOST welcome.
I'm running build 8.0.0.35 on Windows Vista.

Thanks for the suggestions Jacob. I just tried the Convert ID3 Tags -- trying a few different options with no luck.
By iTunes MP3 converter, I'm not sure if you're referring to a feature inside iTunes -- which I don't seem to have (the only option is "Convert to Apple Lossless," which does work by the way but just seems awfully silly) -- or some external application. Could you clarify?
Many other MP3s work. I'm trying to analyze the differences between the ones that work and the ones that don't and have yet to see a real pattern. It seems more likely to happen with variable-rate encodings, but even that's not consistent...
I will say this--the ones that don't seem to be older MP3 files. Which kinda makes me wonder if it's not ID3-related... Do you have specific suggestions for which options I should try out with the "Convert ID3 Tags" option?
Thanks again!

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razzbust wrote:
...but the films won't copy and comes up with message videos not copied cannot be played on this ipod
Self explanatory.
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Was not copied because it cannot be played on this ipod

I am getting this message when I try to put songs on my ipod.
I have had the ipod for over a year and have never had any problems until now.
I bought an album of iTunes Store, burned an audio CD,imported it into iTunes as MP3 and tried to put the mp3 files on my ipod, but I keep getting the message This song was not copied because it cannot be played on this ipod, This has never happened before, any help appreciated. This is the way I have always managed my purchased music, has something changed within iTunes to stop you from doing this??

I'm having the same problem with files purchased from Apple, burned to CD, then imported as .mp3 files. The problem just started recently. This needs a fix as it is very annoying and makes me want to ditch this IPod.
The two solutions proposed in this forum will work but...
Rebuilding the library is very time consuming when you have a library with 30 GB. The other work around of removing files from the library then reimporting them also works, but is very time intensive for multiple files. Is there a way to get word to the folks who can fix this??
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Greetings Smallen8,
Welcome to the Apple Support Communities!
I understand that while trying to sync a video from iTunes to your iPod touch, you receive an alert that the video cannot be played on your iPod. This can happen when you attempt to sync a HD video to your device. Please refer to the attached article for more information.
iTunes: Sync purchased HD videos to iPod or iOS device - Apple Support
When you try to sync a purchased HD video that isn't optimized for your device, you may see a message like this one:
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iTunes: May be unable to transfer videos to iPhone, iPad, or iPod - http://support.apple.com/kb/TS1497

My MP3s cannot be played on this iPod?

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