I replayed Vampire: The Masquerade — Bloodlines (2004) recently

Carmaggedon(1997), via a reverse engineered dethrace

Warcraft 3 custom maps still drag me back sometimes.

Factorio 2016

Well, I don’t segment my backlog for years, so I wouldn’t know which is the oldest one, but the one I plan to play next is Fzero for the SNES which was released in 1991.

I play dungeon keeper a bit. It was released in I think 1994 or 1995

Edit: I also play insaniquarium sometimes too. That shit was from the 2000s I believe

Knights and merchants

Solitaire and Minesweeper. Literally the best games for when I just want to play something that doesn’t require a lot of attention (no story lines, long load times, or remembering what I was doing the last time I played). Just enough to focus my attention while waiting around, but able to close out when whatever I was waiting on is ready. Just really calming for the most part.

breakout. I think it’s the oldest ‘playable’ game. It feel ahead of it’s time for the late 70’s

Bejeweled 3 zen mode on my Xbox 360 till my Xbox one X

I Have No Mouth and I Must Scream
Doom II
Super Mario Bros.
Metal Slug

I still play a phone sudoku game from 2009. I would still play StarCraft and Warcraft 2 if I had hardware capable.

I’ve been playing jet moto with my kid. Just like I did with my dad, back in 1996.

Wing Commander on the ol’ Dosbox.

Just booted back up chrono trigger