I have an iPod Classic that's at least 11 and at most 19 years old. I bought it used in 2015 or so, enamored of its 80GB hard drive. Last year, I finally modded it to have a 30,000 mAh battery and use a 128GB microSD for storage. Unfortunately, due to firmware restrictions, I can't go bigger than that without rooting the device, but I don't mind. I have a Bluetooth adapter I can plug into it to use with wireless headphones, but I also like using it with wired cans. It can't sync with newer versions of iTunes or something, so I have to use iTunes 12 forever. It's kinda cumbersome to make playlists on the fly but I do it anyways and rename them when I get home.
I love it to pieces.