Transferring Music to IPod

[Dirty Dan]

I heard that I could use Winamp to transfer music from my computer to my old IPod nano without using ITunes, and it did seem to work really well when I tried it. But when I go to play the songs on the IPod afterwards, lots of the songs would stop playing part way through and skip to the next, some only 3 seconds in! I went back to my computer and played the songs on there fine, so it must be something going wrong during the transferring process. Any idea what might be going on?