Funnest old gen to replay?

Gen 2.

I don't have a particular reason other than liking the art style. I'll alternate between Gold/Silver/Crystal.
 
My favourite gen is Gen 2, and I feel like I'm always replaying it lol. Once it was released for Virtual Console I attempted my "fullest" playthrough, where I was actively filling the Pokédex, taking my time between gyms and raising a full team instead of just my starter like I did as a kid.

There's also a lot of playability in their remakes thanks to the addition of the Battle Frontier. I always get a bit sad after defeating Red in GSC, as there's really nothing left to do in the games but I don't want to stop playing them lol.
 
gen 4. Not only I am attached to the games, but every time I play I get nostalgia, but especially I just love the style of the games. It always gives me positive vibes: I love the story, the music, the pokemon, the characters. I mean, i guess everyone knows it's my fav gen and it is for all these reasons. Also I like all the small details, even in the dialogues, that I read and interpret every time and that's how I ended up having my "theories ì" and speculations. I played pokemon diamond around 10 times and platinum 6/7 times. I replayed all games actually (except sword) but pokemon diamond and platinum the most.
 
Gen 6 and gen 7. Though I guess those aren't old enough =p

Guess I'd go gen 4 then for HGSS. I haven't actually replayed these that much, but for pre-gen 6, it's the only ones I'd consider replaying at all =p
 
Legit, Pokémon Yellow (original GBC release). I adore Johto and it will always be the core series game closest to me, but I found that upon replaying Yellow, there is an undeniable charm to it. It felt like taking a direct hit to the nostalgia funny-bone and I could help but be enamored with the game, with Pikachu, and the anime plot beats it follows.

During those replays, I always felt like Pokémon Yellow went the extra mile. Little things like Charizard being able to learn Fly, the addition of few updated sprites, Jessie, James, & Meowth, and more anime accurate ace Pokémon the Gym Leaders use.

But obviously, the most fun and replay worthy moments are all about Pikachu. I adored that he would follow behind you and I remember constantly talking to him and hearing that 8-bit "PIka" sound that changes in tone depending on his mood. I loved making notes about the items/events where that sassy, defiant lil' rodent grew more accepting and friendly, and would eventually develop a trusting, loving bond with the player. Oh! And finding all the actions/locations where Pikachu would display a unique mood — like falling in love with Clefairy and wearing a hat while fishing (which isn't an emotion but COME ON).

I know this mechanic was made to mimic the anime, but they didn't need to give Pikachu so much personality. Pikachu was so interactive and so emotional, it was impossible to not find yourself truly, emotionally connected with those pixels. Experiencing all the highs and lows. The idea of earning a Pokémon's respect, or distain, gave Pokémon Yellow endless replayability for me.

Also the Surfing Pikachu mini-game of course!! My lil'electric boi was a champ! Those moments of genuine pride I felt, or shame of losing, the worry when Pikachu was poisoned, the preciousness of him falling asleep to Jigglypuff's song, and the absolute delight of knowing I would always have a best friend in Pikachu. That's what makes Pokémon Yellow such a fun and unique journey worthy of numerous revisits. ଘ(੭ˊ꒳ˋ)੭✧
 
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I like replaying gens 1-3 the most. They are a lot faster to get around with cutscenes being only few and far inbetween. I'm a little iffy on gen 3 in that regard, though. Especially Emerald made things a little bit annoying with all the random "let me call you to tell you that I added your phone number".
 
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