There is actually a very well-developed and customizable project for classic Apple iPods and some other music players: Rockbox. There are even manuals for the various devices (for example, here for the 6th generation iPod Classic).
You can expect many new features:
- New games and applications
- A wide variety of themes, with something for every taste
- Voice output for control functions
- And much more
An ideal basis for modders and anyone who likes to customize things down to the smallest detail.
Even better: many new audio and video files are supported, including FLAC:






With Rockbox, you no longer need iTunes for data management!
As a fan of jailbreaking and modding of all kinds, I’m particularly excited about this great project. It’s the perfect addition if you have an iFlash installed, but it’s also really good on its own.
Installation
Simply use the Rockbox Utility; instructions can be found here.
Enjoy!