Originally Posted by David Munch
iTunes hasn't sold DRM music for more than 3 years, so I assume your music is from before you got the iPod?
If you want it un-DRM'ed, you can by iTunes Match for a single year (One time fee of 25$), and it should "upgrade" all your music to DRM free (And higher quality in some cases).
Yes, some of my music from iTunes is older than three years old. I was thinking about doing iTunes Match after reading about it yesterday. De-DRM'ing is an incentive I didn't even know about. Thanks for mentioning it.