Anapod explorer is good for loading songs and files onto your ipod, just brings the ipod into Explorer like a normal drive and also converts song files to aac or whatever apple uses. If you want something to just play your music, then fubar, winamp, etc.
Winamp 5.5 has iPod support but I can't find any firm info on which iPod version it supports. It definitely supports everything before classic, probably supports classic, and does not support the touch.
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