I still have my original Game Boy that was a gift from my aunt and uncle. Still works but I rarely play it; need to find some of my other games for it.
I think it's the NES for me too. It was my dad's, and he kept it in good condition. He mostly only had sports games for it though, and Super Mario Bros. I've heard the NES came with a combo cart for SMB and Duck Hunt, but we don't have Duck Hunt and Mario is on its own cartridge. We also don't have a R.O.B. I have no idea what that says about what time period or in what package combo he might have bought the NES.
Most recently, I got a copy of Super Mario Bros 3 and I've been playing through that. I also still like buying new games for it whenever someone like Limited Run publishes them. When I was there last, I bought Alwas Awakening and it sure feels wild to be playing a game on the NES that's also sold on Steam.
The oldest system I have would be the NES. My brother received it sometime before I was born. I'm just holding onto it for him, though - it doesn't get played right now. I actually intend to clean it all up and retrobright it before sending it back to him... eventually...
The oldest system I have that still gets occasional use would be my Gameboy Color, which I received, with Pokemon Red, for Christmas when I was 8 or 9. Unfortunately, I need to find a better plastic polish, to take some light scratches out of the lens, and until I do, it will remain disassembled... I've also been contemplating using the board for a complete boxypixel overhaul, but there's something about still having my full original GBC that I'm having a problem getting over...
My Commodore 64. I have a ton of cassettes and floppies with games. Some even with intros from scene release groups, which are pretty fun. I should probably digitize them at some point to preserve them. I don't use it much though due to the risk of the original power supply frying the computer. I'll have to buy a modern replacement at some point.
Ive got a Magnavox Odyssey. Gift from a family member who knew I collected older games. Its a bit older than I can really get into playing but its fun to bring out every now and then.
I still play the Intellivision's Treasure of Tarmin on my phone from time to time. People would probably call it a first-person roguelike or something today. Amazing how a little randomness can give even a 1983 game so much replay value.
For actual hardware, I doubt I'll ever play anything especially retro/vintage now. I'm spoiled by today's gamepad ergonomics (I'd never play much Treasure of Tarmin on an Intellivision pad, woof). However, I do sometimes think about setting up some sort of hardware to play on a CRT with a wireless gamepad.
MegaDrive. Don't remember how I got it, I just always had it. I don't play it that often if at all anymore as I prefer the ease of emulating on my HTPC with retroachievements. Even got a nice saturn style fight pad that works great for MD games.
Also the model I have is the region free Asian one even though I live in the UK. I've always had a JP copy of sonic 1 too. No idea how they ended up in my hands.
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