Hi Grumblebum.
If you take a look at
http://support.apple.com/specs/ipod/iPod_classic.html it will show the following audio formats supported by the ipod:
AAC (16 to 320 Kbps), Protected AAC (from iTunes Store), MP3 (16 to 320 Kbps), MP3 VBR, Audible (formats 2, 3, and 4), Apple Lossless, WAV, and AIFF.
It might be you have ripped the song into the wrong format.
Winamp may play these songs fine,but it looks like itunes will not support this format. I looked at the winamp website and see the format you mention. My suggestion would be to re-rip those cds into a MP3 format. Hope this helps.
Message was edited by: david-iPod80Gb