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It's important to note that good visual design goes a long way. Gen 1 had some of the most iconic designs to the point that a lot of later ones felt like copies by comparison. And people are going to remain loyal to the more likeable designs from more orginal games if the gameplay stagnates with later ones (as the common complaint goes).gen 1 is the worst Pokémon gen
It kind of reminds me of how the player base for Cube 2: Sauerbraten never really got that big despite the game being a totally free CS/Unreal Tourny clone. Sure, it was a fun game, but it was just downright ugly, and the devs never made any effort to make likeable characters, leaving players with 4 ugly generic ones to choose from.