3rd generation with the four buttons bought in 2003. I still have it but it's been dead for a few years. It feels like an absolute brick compared to my 5th gen. nano. I've owned two classics, a mini, and a nano and that little 3rd gen. beast was by far my favorite.
I never did the iPod thing. In my mind, there were tons of competitive products with similar or more storage for a fraction of the price (and usually, more features like FM radio). So my first iPod was my iPhone 4 32GB I got in 2010!
That said, I really do like the accessory market, compatibility and integration with everything, and how much better it plays with iTunes, et al. Definitely the best mp3 player out there, but it took them adding a smartphone into it to finally sell me. That kind of a feature is hard to look past
2nd generation iPod touch was my first. It started my downward spiral into the Apple universe. Now almost every piece of tech I own has an Apple logo on it.
My first iPod was a 2nd gen touch. I then moved to a zune after getting mine stolen. Then a 3rd gen touch followed by and 4th gen touch then a second gen nano. Finally the iPhone 4.
nano 4 gen, in early fall '08. I bought it in the green, because I have a weakness for green in general. I was pretty happy with the color...until the next generation came out and the lineup included a gorgeous, dreamy emerald green that was *exatly* my favorite shade of green
It burned, but I got over it quick because I knew I had gotten mine when I honestly needed it, not just as a random whim - my ancient little creative Muvo from like '04 had finally given up the ghost Of course, it could be that what made the biggest difference was the brand new iphone that was in my pocket and piping music in my ears when I saw those new ipods
But I didn't stop using the ipod, it actually turned into he perfect setup because I began to use the ipod for hooking into my sound system at home (and in the car for road trips) so even though I got my iphone when my ipod was still fairly new, I still got tons of use out of the ipod. Still am!
30 GB black iPod Video, purchased in December of 2005, and still in fairly regular use. The battery only lasts a few hours now, but I mainly use it docked in my speakers in my kitchen, so not too big of a deal.