On the PC, I've sometimes been playing PC Kaiser, although no idea when it was actually made.

I just got my RetroPie running, which has led me to replay some games from my past, including N64 games such as F-Zero X and Star Fox. I also had a Sega Master System II in my youth, the oldest game I played back then being Alex Kidd (1987), the oldest game that I'd replay is probably Asterix from 1991.

 

Recently replayed Cosmo’s Cosmic adventure (1992), which was every bit as fun as I remembered.
Also an eternal favorite of mine, the Commander Keen series (1990-1991), which I revisit every couple of years. Out of those, Keen 4 is by far my favorite. Platformers don’t really get much better, nor do they need to. Give them a try if you’re not familiar with the games!

Pokémon gen1 is the oldest I come back to more than once every few years, though gen2 is, for me, the peak of the franchise. Maybe because I was at the correct age at the time they came out, playing a (atrociously) fan-translated version of Gold on No$gmb emulator. This was in spring 2000, before the game was officially released in the west - my mother worked in IT and thus had colleagues that were delightfully savvy with such nerdy stuff already in the 90s. Good times.

 

While M&M 3 is still awesome to this day.

Medieval 3 total war. Is a game a always come back to. I have 600 hours on steam, and at least 500 while it was on disc. Sure it doesn't look as polished as warhammer total war, but the mechanics in m2tw hold up to this day.

If you change your infantry´s position, then there will be some delay on some of your troops.

If you suddenly make your whole army charge, then there will be troops who are slower to respond.

All of your archers do not shoot in unison like in The Hobbit, and they don't all have perfect aim.

And sure, you can endlessly chess the AI. When you know the game, then there is no challenge after the early game.

But, no game has ever captured me, in the same way as m2tw has. It is the er perfect blend of turn-based strategy, empire-building, and real-time battles.

And nothing beats watching all of your heavy cav ride down your enemy like the rohirim.