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N64 was the worst. From the terrible layout and ergonomics... to the the overly busy buttons and questionable design choices; like the need to add directional face buttons. Then, you have that loose, clunky analogue stock in the middle. Yeesh. There are bad controllers from every generation but at least every other modern controller are designed for people for two hands. And from this planet.

Gamecube is a close second. Ridiculously large A button. Then bean buttons on top of that. On top of that, that god awful C stick. Oh, and those spongy analog triggers. >_>