Steam Deck

If you count DOSBox as emulation (what it definitely is - unlike WINE it actually emulates an x86 PC and peripherals):

• The Settlers 2: This is a timeless classic. The graphics are 2D, but they still look OK today.
• Albion: A Science Fiction and Fantasy RPG (yes, it has both, and that'a a key point of the story). The gameplay itself isn't that great, but the lore, story and the graphics are amazing.

I've played both on the Deck, and they both work great. (Btw: I did not use Settlers 2 as an example for my DOSBox setup guide by chance. I picked it because it is an amazing game and still fun nowadays.)

I play through Donkey Kong Country 1 and 2 at least once a year. It is largely nostalgia for me, but goddamn those games are fantastic.

3 is much less so, unfortunately.

Yoshi's Island is also worth diving into. One of the best 2D Platformers ever made.

That really depends on your definition of "holds up".

For example, to me the original Final Fantasy VII is still a better game than the remake because what was a well thought out RPG combat system got turned into just another button mashing combat experience with a Final Fantasy VII wallpaper applied to it.

Is the remake better graphically? sure. Does that matter to you? Than yeah...the original isn't going to hold up for you. But if you prefer the classic design from those times, the game holds up great from a gameplay/story/character perspective. And I personally would take it over whatever mash-fest modern games use for combat systems.

F-Zero X on N64

A lot of PS2 games have busted PC ports or ports with invasive EULAs. PS2 is still probably the best way to play GTA: San Andreas.

But really, just pick a console with a graphical aesthetic you like and find the games people buzz about. I'll give you some recommendations, based mainly on my taste, but a quick "(console) best games" search can help you expand upon this.

NES: Mike Tyson's Punch-Out, Super Mario Bros 3, Kirby's Adventure, Castlevania, Mega Man 2, Contra

Genesis/Mega Drive: Streets of Rage 2, Castlevania: Bloodlines, Road Rash, Sonic 2, Contra Hard Corps

SNES: NBA Jam: Championship Edition, Mega Man X, Star Fox 2

PS1: Crash Bandicoot 3: Warped, Crash Team Racing, Tony Hawk's Pro Skater, Metal Gear Solid

N64: Super Mario 64, Star Fox 64, Banjo-Kazooie, Mario Kart 64, The Legend of Zelda: Ocarina of Time

Dreamcast: Sonic Adventure, Sonic Adventure 2, SoulCalibur

PS2: GTA San Andreas, Tony Hawk's Pro Skater 3, Tony Hawk's Underground 2, Resident Evil 4, Silent Hill 2, Metal Gear Solid 2 & 3, Kingdom Hearts, Kingdom Hearts II, Sly Cooper (entire series)

GameCube: Super Mario Sunshine, Mario Kart Double Dash, The Legend of Zelda: The Wind Waker, Super Smash Bros Melee, SoulCalibur II

Xbox: Halo, Halo 2, Fable: The Lost Chapters

That's a decent start, but not comprehensive by any means. Just pick a console with games you like the look of and search the top-rated games, the cream really rises to the top when you're looking for retro games.

I personally think smaller scale 2000s collect-a-thon games like Ty the Tasmanian Tiger hold up pretty well. Never knew that specific series existed until maybe a year or two ago and I gotta say, it's pretty good and runs real smooth on Dolphin on my Steam Deck ( and coincidentally better than the legitimate PS2 copy I have ).

I personally also think the PS2 Star Wars Battlefront games still hold up well enough. Love the lack of monetization and lack of online play because I hate competitive play as a more casual player.

Those games are definitely pass my recommendation checklist due to the amount/quality of content, and/or replayability level.

Another couple games that pass that checklist would be Final Fantasy X ( I never finished it, but had been enjoying it all the way ) and Sly Cooper 1 ( due to the time trials for each non-boss level adding a good amount of challenge and length ). Both on PS2.

The PS2 version of Shadow of the Colossus still looks great to me.

Sensible World of Soccer on the Amiga

The 2D Castlevania games still hold up well, except the NES ones for being NES hard. Most of them are available for purchase through collections.

I've been playing Gravity Rush from the PS Vita. I went in blind and have been enjoying it so far. I can't get motion controls to work, but that hasn't stopped me yet.

Incredible Hulk: Ultimate Destruction

I was worried that I was just nostalgic but its honestly a straight up blast to play. If they remastered it I would b e so excited. One of the best superhero games I've ever played.

the Metal Gear Solid games on the PS1 and PS2 are still wonderful games. The controls may be a bit clunky, coming from modern games, but you get used to it after a while. (There's some things you will have to look up on the internet in MGS1 because they require information from the CD case lol)

I always liked the Megaman X games on the SNES as well.

OK, let me fix that for you permanently.

This is Retroachievements.org.

Not only does it do what it says on the tin, but it's, for my money, the best discoverability tool out there for old games. The most obvious way to use it for that is to check the new games they've added achievements to, but they also have book club-style events (they're revisiting F1 games this month to go with the movie currently in theatres), challenges, seasonal achievements, leaderboards and all sorts of the types of metagaming stats tools you've seen in modern platforms to point you in the rigth direction.

You can start by selecting "all games" and sorting them all by players to see what's popular. Or, hell, reverse sort by players and see what weird crap is in there. Once you start down that rabbit hole you're more likely to have too much in your retro backlog than you are to ask this question again.

I was playing shadowrun genesis again awhile back. It actually used the pen and paper rules from the time and was pretty neat considering. its like how the text based rogue likes are still fun. does have a few annoying bugs though.

Metal Gear Solid 1-3

Honestly depends on what kind of games you like.

Many Metroid games are classics and still great to play. For the 3D Metroids, you can install Primehack and play Metroid Prime Trilogy for an amazing experience. For the classic style 2D metroids, I'd recommend a play order of Zero Mission (GBA), Samus Returns (3DS), Super Metroid (SNES), and Metroid Fusion (GBA).

Many older mario games are great, both 2D and 3D. Mario 64 has some great recompiled versions, and even stuff like sm64coopdx that lets you play online coop. Mario Sunshine (GCN) is fun too, and both Mario Galaxy (Wii) games are fantastic. Lots of good Zelda games too, such as Wind Waker (GCN/WiiU). Until recently I would have highly recommended Xenoblade X (WiiU), but it just got a remastered and expanded version on switch.

Terranigma (SNES)

There's a world of options out there and you need to be more specific with what sorts of games you enjoy. I've been emulating on my Switch for a while, but also recently bought a dedicated retro emulation console so I have quite a few recommendations.

For games that are literally still up to modern standards, you can go back to Wii, 3DS, PS Vita, PS3 and beyond and you've basically got games that will still hold up just fine.

For older games: PSP, PS2, SNES and GBA are gold mines of content.

I've found it difficult to get into PS1, N64 and Dreamcast gaming. This was a time when 3D graphics were just starting to be widely used and are so very dated. It's difficult to look past the terrible graphics without nostalgia goggles. I've had more success in going back to SNES and Mega Drive games.... At least they have great pixel graphics with suitable games (side scrollers, platformers, etc).

For specific games, I find it best to go to metacritic and look at their list of all time best games, and limit by console and then work through the best every reviews. This does miss a lot of games though and if you say what sort of games you like then people can make recommendations. There are tons of hidden gems and niches..... Rhythm games, block drop, quirky puzzle games, etc. E.g.:

Everybody's Golf 6 (PS3) - excellent arcadey golf game

Mercury Meltdown (PSP) - puzzle game about manipulating mercury blobs. Great to play entirely with the Steam Deck gyroscope.

GTA China Town wars (PSP) - top down GTA game, modernised beyond the GTA2 controls

Rhythm Heaven Fever (Wii) - excellent rhythm games

Super Mario 3D land (3DS) - 2.5 D Mario. Really solid platformer.

Wipeout 2048 (PS Vita) - solid combat racer

Micro machines 2 (Mega Drive) - quirky top down racer. Excellent for multiplayer.

Crazy Taxi (PS2) - taxi driving, really crazy though

Wario Land 3 is a game design gem

Paper Mario

Intelligent Qube (PS1)

I like playing brawlers/beat'em ups. They are really straight forward and don't require any quality of life upgrades.

NES: Contra, Bubble Bobble, Faxanadu

SNES: Super Metroid, Kirby Superstar, Chrono Trigger