Have a look at these:
<a href="http://www.ephpod.com/">ephPod</a> is a Windows application but runs perfectly under WINE on Linux.

I never tried these, but they look promising:
<a href="http://www.floola.com/modules/wiwimod/">Floola</a>
<a href="http://www.sturm.net.nz/website.php?Section=iPod+Programs&Page=SharePodLib">SharePod</a>

Apple's DRM sucks.