[patrickk]

iPod Classics also refuse to die, I'm using a used one I got cheap on eBay. You can also mod them with open source software (escaping the clutches of iTunes), install a higher capacity battery, replace the case and install a power-sipping micro SD card - if you so wish. It helps that it's not tied to a cloud service, you can get an older version of iTunes if you really need it. More details[1]

[1] https://news.ycombinator.com/item?id=19712077

[OrangeMango]

I found a couple of old iPods in the bottom of a box in my closet a month or two ago. My kids were interested so I dug around until I found one of those 30-pin cables. Plugged it into my Mac; it worked fine. I transferred a bunch of songs they wanted and the kids have been listening to them since. For one of them, Apple even had a software update available for it.