iPod stops song halfway through.

This has happened for a long time, but it's finally bothering me enough to want to fix it... and before you ask, yes I did the 5 R's. Even though they all play perfectly fine on iTunes and Windows Media Player, certain songs I upload to my iPod will play and then maybe 30 seconds from the end, it will suddenly stop and the position bar skips to -01 seconds (1 second to the end). It then freezes for maybe 10 seconds and goes to the next song. Can someone PLEASE tell me why this is happening, it's incredibly irritating. As I said, I've tried the 5 R's, and I've tried reuploading the songs by unchecking and rechecking them in iTunes about 1000 times... I've even tried re-encoding the MP3's at a different bitrate. One thing that sometimes works is when I go and physically cut maybe a second off of the song with my audio editing program, but since this particular album has songs that lead into each other I can't do that in this case.

Either way, this shouldn't be happening and seems completely random. HELP!!!

Windows XP Pro