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Worst one for me was funnily, from the Hitmon family. There's two specific guidebooks that say that Hitmonlee evolves into Hitmonchan, and that by gen 2, you need to evolve Tyrogue into Hitmonlee, and then it will evolve into either Hitmontop or Hitmonchan.
Actually fucked with my brain all the way to gen 6, thanks shitty guidebooks from the mid 2000s