The first Sonic the Hedgehog for the Mega Drive. I play all 3 (4?) of the original Sonic games, but that’s the oldest though.

I play through my Mega Drive games occasionally. Alex Kidd is probably older… Wonder Boy is great, too!

OpenTTD (2004), which traces its roots to Chris Sawyer’s Transport Tycoon and Transport Tycoon Deluxe (1994)

And there’s a community of players who have modded the everloving fuck out of the game and the engine itself, one of these patch packs is OpenTTD JGR and we play it like it’s a model railway simulator

On the regular I still fire up Zork 1-3, Ultima 4, StarTropics, OG Metroid, and Maniac Mansion.

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

Warcraft 3 custom maps still drag me back sometimes.

Carmaggedon(1997), via a reverse engineered dethrace

Knights and merchants

Factorio 2016

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

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.

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

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

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

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