Personally, I just used iTunes to compress the less, um, significant tunes in my collection. Then I left the stuff I really care about in Apple Lossless.
This got me under 113 GB, which to my memory is about how much an iPod Classic can hold (i.e., 120 GB minus the software, etc.).
This got me under 113 GB, which to my memory is about how much an iPod Classic can hold (i.e., 120 GB minus the software, etc.).