UnderwaterFunktown 14 hours ago
You can seperate it into handheld and home consoles if you want or just take one per generation. PC games also count if they fit into that era.
For me:
Gen 5 - Pokémon Crystal on GBC
Gen 6 - Pokémon Ruby on GBA, Tales of Symphonia on GameCube
Gen 7 - Probably Diablo 3 on PC with StarCraft 2 as a close second
Gen 8 - Many games tied for 2 playthroughs: Persona 5, REmake 2, The Stanley Parable, Deltarune. I think the only one with "more" is Hades (which is kind of cheating)
Gen 9 - Haven't played anything multiple times yet unless I'm misremembering
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