The iPod Video and lower had some pretty incredible tools and firmwares available looking back. I was part of the iPod Wizard team (mostly helped with mapping hex locations on new firmware releases and created a handful of themes, including backporting the color themes to the 4-tone generations) and contributed a bit to the iPodLinux project. At one point, I had a bootloader that let me switch between the normal firmware, Rockbox, iPodLinux, and iPod Wiki (all of Wikipedia viewable offline on your iPod) available just be restarting my iPod. It was a dumb smart phone half a decade before the iPhone.
The devs on those teams really pushed that little MP3 player to do things it was never intended to do.
The devs on those teams really pushed that little MP3 player to do things it was never intended to do.