Oldest game I still play is probably Taipan.
I first played it on an Apple IIe, but now it is just a web browser thing I poke at once in a while. It is basically spreadsheets and bad luck. You trade, pirates wreck you, the math never quite works out, and you lose anyway. I think that is why I still like it. No graphics to hide behind.
After that, Seven Cities of Gold, usually on a C64 emulator. That one still holds up more than it has any right to. You sail off thinking you are doing something heroic and slowly realize you are kind of a problem. The exploration feels lonely. The map still feels bigger than it actually is.
But the oldest one I keep coming back to is Gorf on the VIC-20.
I owned the cartridge. Bought it not long after it came out. I paid for the VIC-20 by walking beans and putting up hay all summer for a farmer when I was eleven or twelve. Hot, dusty work. Long days. I remember counting the cash and realizing I could actually afford a computer.
Gorf was loud, ugly, and mean. The voice mocked you constantly. The joystick barely survived. I loved it anyway. Sitting on the floor, TV buzzing, thinking this was the future and I had somehow managed to buy a piece of it.
Also, side note. I am trying pretty hard to become a professional writer. I write essays and stories over at tover153.substack.com. If anything there hits a nerve, feel free to subscribe.
So yeah. Taipan, Seven Cities, Gorf. Not because they are good by modern standards, but because they still feel like something.
I am realizing my life is not really marked by birthdays, anniversaries, promotions, or any of the normal milestone stuff people list. It is marked by video games.
Thanks for this thread, because it reminded me of one I cannot leave out.
There was a week I spent in a mental hospital with a major anxiety spiral. Pretty much everything felt unmanageable. The one thing I could handle was Pokémon FireRed on a Game Boy Advance.
That was it. That was my anchor.
It was actually written into my chart that I was allowed to plug my charger in at the nurses station while I slept so the GBA would be ready the next day. No arguments. No debates. Just accepted as necessary.
Not my oldest game, see my other replies for that, but it is probably the only one I have mentioned that might have saved my life.