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I would say the original NES controller. I loved the console, as well as the controller's simplicity, but those sharp edges made long gaming sessions hell. I would say the N64 controller was never uncomfortable to hold, but it has to be one of the worst designed controllers EVER. You had to reposition your hand to make use of the Dpad and L button, but this also left the analog stick and Z button unreachable. And while I have never used it, the original Xbox controller does look like a nightmare to hold.

On the flip side, I do love the Dual Shock.