ha theres a software called "ipod rip" that you can get for free 100 songs, or pay like 10 bucks for the whole thing, def would get that. i haave it, works awesome.
just google it, there are so many ways to do it for free and ways to do it without special programs. i did it not to long ago but i forget what i used.
i used it but like every 50 songs it asks u to purchase the program but u can just say no or x the box out and it will keep goin and it does movies too
I used something a while back that was free forever and worked perfectly. It was called pod util. I got it at download.com. I tried to find it on there but now it is gone. You might wanna look for it though, it was freeware.
set your ipod to disk mode (restart it and hold center button and left arrow) and then plug it into your computer. It should come up as a usb hard drive. Go into folder options and select show hidden files and folders (if you haven't already) and open up the hidden folder. Inside is another folder called music which is full of your MP3's with random letters as titles. Copy the entire folder back to your computer and then use a program called Tag & Rename (google it) to automatically give them proper file names.
i have ripped songs manually as eric did above, but i use a program called podlift to rip songs now because it allows you to view and sort music in the same categories as on itunes, although frustratingly not by date added...
yea i used that a while back and it works, but if you have a lot of music then you have to sit there and keep cancelling the offer to buy it the whole time or else it won't continue.