I have a working 1st-gen iPod that I bought right after it was first released (around the end of 2001 or beginning of 2002). It loads up normally in the newest version of iTunes. I recently used it to listen to music on a coast-to-coast flight. That way the iPhone can be shut off and have a full battery when I land.
I updated its hard drive and replaced its battery recently. If your iPod is a 1st-gen, you'll want to find an old firewire car charger on eBay to charge it while in the car, and you might need a firewire-to-something converter for you current computer if you don't have firewire on the current computer. You can also get an old-school FM transmitter to plug into its headphone jack if your car stereo doesn't have a 3.5-inch jack in it.
Also on the old-tech front, I am typing this post on an original Mac Pro (2006) that I got for free on craigslist.