All my controllers from Mega Drive onwards PS, PS2, 360 etc are in perfect order, I mustn't use them enough :|
N64 analogue sticks + Mario Party = We got to the point that the person with the newest control pad (and therefore stiffest analogue stick) would usually do best in Goldeneye death matches.
Never had a proper keyboard wear out, although this one's getting a bit weird now. The worst has to be the damn stick on the N64 controller - it wears out so often, and it's vital for so many games. We used to play multiplayer mariocart last year, and no-one ever managed to finish a lap without once crashing off something from poor sticks... I always thought someone could make a mint from re-manufacturing N64 controllers and selling 'em cheap, because so many people still love and use theirs.
Oh well if we're going down the keyboard route, I stuck with a return key long after it had become ...unstuck. I think it's mostly due to my 'enthusiasm' after a lone of code; I do hit it fairly hard. It got to the point where I would slam down on the key causing to to bounce up out of its holding and fly across the desk.