Use iPod Classic Without iTunes

You could try using Rockbox, however you might want to check whether or not your iPod is supported. Rockbox is an alternative firmware for your iPod classic that allows you to copy music files just like a normal MP3 player.

http://www.rockbox.org/wiki/IpodFAQ

It even plays Doom!

You can use Foobar2000 which is an amazing music player and manager for Windows. There are dozens (if not hundreds) of add-ons, one of which adding iPod control. I personally use this software and it makes managing songs on the iPod very easy.

The iPod components has many features and supports album artwork. It also gives you the option of converting unsupported audio formats (such as FLAC) when you add those to the iPod.