For me it’s Chrono Trigger. I always want to play it. I want to show it to my children. I hope it will be regarded as a masterpiece for generations to come.
The Legend of Zelda: A Link to the Past
From the art to the music to the plot to the gameplay, it’s just iconic.
Super Mario World! It holds up remarkably well even by modern platformer standards. It feels great, looks great, and is a blast to explore.
I honestly feel a little disappointed that I scrolled this far and nobody mentioned Age of Empires II: The Age of Kings (1999).
This is an RTS game, which is a dying genre. It’s also a 24 year old game, which after its release two more Age of Empires games have been released as well, and the game itself has been remastered recently. Yet people continue to play the original game to this day, the multiplayer scene and competitions are still active.
If that is not timeless I don’t know what is.
Community consensus is that AoE 2’s mechanics are an improvement on its predecessor, but I personally have a weak spot for AoE 1: Rise of Rome expansion. Fewer things to manage, beautiful wonder structures, and cheap axe man hordes.
My dad and I used to play against each other over LAN. Hearing him shouting and cursing from the other room while I razed his city with scythe chariots is such a happy memory. Man, I miss him. To the dads here, play AoE with your kids.
DooM (1993), but mostly because of the community. Constant new levels, mods, engine updates, total conversions. Even commercial games released on the engine. It just never stops.
First off you’re gonna want to grab yourself a source port like GZDoom so you can run it on a modern PC with all the extra bells and whistles. Go grab the original DooM and DooM 2 off Steam for $10 each if you somehow don’t already have them. A lot of stuff still needs access to the original .wad files.
Then check out Doomworld, the Zdoom forums and modDB for a literal ton of extra content. I suggest checking out Brutal Doom, Rekkr, Ashes, Sonic Robo Blast and Hedon for examples of what the modernised engine can do.
Fair warning though; because the mod scene is so active, you may have to sift through a lot of cruft to find something that appeals.
While I do love the things people have done with GZDoom, I always find myself coming back to a more classic doom experience. Something like dsda-doom that tries to stick to rules of the originals is more my jam, and it has some nice quality of life features that don’t alter the core gameplay. There is just something about the basic and simple mechanics of base Doom II that is timeless.
If you are looking for quality WAD recommendations, there is a continually updated Doomworld Community Top WADs of All Time or you can check out the annual Cacowards that attempt to acknowledge the best new doom content created every year. Many of these wads dramatically outdo the originals in terms of map design. Eviternity—a favorite of mine—which comes in at #6 on that list actually had it’s creator scouted to do the maps for the boomer shooter Prodeus .
Also, even though I prefer the classic experience, my favorite weapon mod has to be Final Doomer. Brutal Doom always gets all the hype, but this one deserves a lot of love for the fact that it tried to add weapons to fit specific wads. It gave the wads it was made for so much more flavor, and, while definitely more powerful than vanilla weapons, it wasn’t to an absurd level like brutal doom.