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What's your most replayed generation/game?

Gen IV, I think - I've replayed HeartGold maybe three or four times, and Platinum twice? Pokemon isn't a series I generally replay - I still have my first Diamond file! - so honestly just more than once is an achievement haha.
 
It's between the 3rd and 4th gen and really only the lord knows how many times I played them and which gen was the most.
 
Generation 4 games! Specifically Heartgold! I've replayed it at least 6 or 7 times, perhaps more. I've also replayed Pearl a countless number of times. I just enjoy the storylines of the games so much that I cannot resist replaying them with a fresh set of pokemon!

I've also replayed Pokémon Mystery Dungeon: Explorers of Sky, Darkness, and Time a million times over as well. Considering the fact that Sky is my favourite game of all time, it's only natural that I've played it so many times.
 
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Gen II, definitely. I love reliving all the changes that came with that game and everything the devs learned from the success of RBY. It's such a comfortable place for me to return to. ( ˘ ³˘)♡
 
Individual game - Emerald. My first, and Pokémon Ranger did not fill much of the two year gap to Gen IV!
Generation - Gen IV. I own the most games from this generation, and have had many saves on Diamond and HeartGold in particular (I think my highest total hours was on a Platinum save, which is why the plot, gym leader order etc. in my head is that of Diamond). I also owned SoulSilver for about a week before trading it in for HeartGold (can't remember why, may have been to do with version exclusives like Arcane, but Blockbuster did me a straight swap I think which was great). GTS was a game-changer for me, I've never traded a pokémon in-person and until 2011/12 only owned one DS system. The ability to trade all my items, as well as bring resources forward from Gen III, means Gen IV is the one where I EV train (purely to see how good I can get my pokémon, I have nobody to battle except the Frontier Brains), breed for egg moves etc.
 
Gen 2 / 5 with Pokemon Crystal and pokemon Black 2. Black 2 was the last good game in the franchise. Nothing can even compare to black 2
 
Generation one for sure. One reason being is that they were the first that I could download on my phone while already having replayed the physical copies numerous times.
 
Mine is Generation 3 without a doubt, I've played Emerald and FireRed more times than I can even remember, or dare to haha. I'd say it's probably between 20-30 times for each game, but that's just a guess, Gen 4 comes in at second for sure as well!
 
It's a mix between gens 3, 4 and 5 for me. I've replayed all of them quite a fair amount. Everything after 5, though is a never for me. Once was enough.
 
Gen 5. I've played white at least 3 times now. (My original save was 100 hours!) Still my favorite game in the series. White 2 and Black 2 are interesting, as I've played both once. (Played b2 and then traded for my friends W2 and linked the save data. Still wish the memory link was incorporated more than it was.) Gen V will always be my favorite pokemon games.
 
Gen 3, 4, and 5 for sure. Mainly the third games and B2W2. I just think they have insane replay value. Anything after Gen 5 I've only played once and that was enough for me.
 
Gen 3, 4, and 5 for sure. Mainly the third games and B2W2. I just think they have insane replay value. Anything after Gen 5 I've only played once and that was enough for me.

Me too, excluding gen 3. In fact, today was my first time playing a hoenn game ( I chose treecko, easier to build a team out of it).
 
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