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NES - Slight discomfort, very sturdy.
N64 - Major discomfort, sticks barely lasts three months of active use.
GC - Extremely comfortable, still using my original after ten years of active use.
Wii - Very comfortable, can't comment much on its durability since it hasn't been actively used. The A button already requires some extra pressure to work though.
Wii U - Above average, no damages so far.

In comparison, while the Xbox 360 controller also falls into the "extremely comfortable" category, I'm currently on my third wireless controller and could really use a new one. As for the original Xbox's S controller, while falling into the "very comfortable" category, had major issues with its wire's durability. Didn't last a year until it was unplayable.

And then there's the dualshock which I have very limited experience with. I can't comment on its durability, but that design wasn't really my style. A lot better than the NES and N64 controllers though.