Which old game is the best to replay for you?

Gen 2. It has a comfortable and warm aesthetic for me. Level curve and flaws regardless. I just find the whole generation pleasing.
 
I think that the ones I've replayed the most are like Ruby/Sapphire and HGSS, for whatever reason
 
I'll always be biased towards Platinum since I consider it my favourite game of all time, but any mainline games between Gens III-V are lots of fun to replay. They're games I know really well and can always feel comfortable with, but (usually) have enough Pokemon in the dex to where I can make an interesting team of Pokemon I've never used before.
 
Leaf Green is usually my choice, as it's the best of the remake games and is usually a relatively quick playthrough when compared to some other Pokemon games. It helps that I have two copies of the ggame so I can keep save data in one while restarting the second one.

Plus, I'll never turn down the chance to step into the shoes of my beloved Leaf-chan :)
 
Hard to say. I personally just can't get back to the pre-physical/special split era, so that discards all the gen 1-3 games for me.

Gen 4 has the problem of being too slow and the excess of HM. I couldn't bear replaying those if it's not on an emulator with the 60 fps unlock.

And Gen 5... well, I'm not a fan of its animated sprites and 2.5d style, and I didn't like B&W limited to just Unova Pokémon.

So I'd say USUM (if those count as "old"), they have most modern QoL, Fairy type, great Pokémon variety, and I found them pretty fun to replay.

Otherwise, either Platinum or B&W2.
 
Gen 6 (especially XY) is very replayable to me. A lot of the older games have a problem where there are only a handful of Pokemon available until a few badges in; which either forces you to use those handful of picks, leading to a similar experience each time. Or delay team building until the game opens up, which makes the first few hours an even more boring slog then they usually are.

ORAS and XY on the other hand give you tons of options right out of the gate, which allows for a far greater variety of playstyles without having to wait 3/4 of the team to actually catch the Pokemon you want. It also helps that they're both super easy, which makes pretty much any team/strategy viable without grinding.
 
I may have hit my limit on replaying the games in general. From time to time I could crack open a new playthrough and happily play through to the end. But since B2W2/XY, I started getting into competitive battling, which made it counterproductive to erase my save file.

Then I became an adult, with a job and other responsibilities, so the games definitely fall under the category of "comfort gaming" for me, where I play them if I'm sick or otherwise unwell, and just want some cozy brain-fodder.

My favourite to replay is always GSC/HGSS, Platinum a close second, and generally anything between gen 1-5 after that. I'd love to replay Moon/Ultra Moon but it just feels too tedious.
 
Gen 5 will always be the most replayable to me. I love BW/BW2 so much. I consider them peak Pokemon in terms of games, tbh. So much love and care went into those games and its sort of shame the games afterwards kind of went in a downward trend imo.
 
Gen 5 here. While it may be inactive in terms of GTS, it is a very fun game to play, and I will play it always. My criticism is that it pretty much killed the franchise because no one wanted to play any other games but Black and White! XD
 
For my person pick, I would say Fire Red and Leaf Green. Recently played through Fire Red in Japanese and I honestly enjoyed it. I think I mainly like it more than gen 1 because of the post game content being fun and having access to gen 1 pokemon with better move sets and abilities feels like the definitive experience. Though I'll admit going through the Elite Four is usually a pain sense it is a sudden difficulty spike. Thankfully the VS Seeker exists.

In second place I would say Heart Gold/Soul Silver because it makes gen 2 a lot more bearable for me. Having the physical special split, easily obtainable evolutionary stones, and pokemon abilities allow me to use Poliwrath at its best. Still has some quirks from gen 2 I don't like as the jump from the gym leaders to the elite four still feels steep, but not as tough as Fire Red/Leaf Green.

Outside of personal opinion, I think Black and White 2 is objectively the best to revisit. The amount of pokemon you have access too and the post game content is well worth completing. It has the fairest difficulty and the game doesn't hold your hand as much like the later games. It has enough challenge and even a challenge mode that makes replaying worth it.
 
For me it's:

1. Hoenn
2. Sinnoh
3. Unova
 
I really liked gold and silver. Platinum was not too bad too.
 
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