I bought the 2009 model on a Black Friday deal, worked out with it once, forgot to take it out of my shorts as I washed them and ran it through laundry. It didn't survive.
I had 6th gen that I also used as a watch for the longest time (with the Mickey face I believe it had). Now I have a Apple watch still using Mickey face. Just realized I went from 6th gen ipod nano to 6th gen Apple Watch (first gen with always on screen). Batter on the Nano is sadly dead now won't hold a charge for a damn.
Had (still do) a 4th gen that was only 2GB. Used it for about a year or so and then got a Creative Zen V plus that was 8GB. The screen on that died, so it got replaced by a 12GB Sony Walkman, which I still like to use from time to time.
Just went hunting for an unused boxed classic I know is here somewhere and found a 1st and 2nd gen nano. 1st gen still works when connected to power but doesn't hold a charge. 2nd gen still works and holds a charge and even has some Giantbomb E3 podcasts from 2014 still on there. Has a weird mark on the screen though and needs the headphone port cleaned out.