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Best: Xbox 360, Gamecube

Worst: Dreamcast, Original Xbox and Sixaxis.

Personally, I never found DS1 or 2 particularly uncomfortable, definitely didn't fit my hands perfectly, but Sixaxis (and I guess DS3) is a joke.

Why? L2 and R2 buttons. Had they extended the bottom of the controller to accomodate this new addition, we would have had a bigger controller that would have fit more comfortably in more peoples hands, instead we get a smaller controller (bottom surface area wise) so that less people will find it comfortable.

Note: There is a difference between acceptable and comfortable. For alot of people, it's the former that's true but they confuse it with the latter.