BEST: PSX
WORST: PS2
In all seriousness, Gamecube's is pretty damn comfortable, and I like how GameBoy Advance's button placement is farther apart than the old GameBoys.
I break buttons easily on Genesis controllers. I have about five of them with buttons pushed in and stuck.

I go through N64 controllers like I go through toilet paper.

And XBox has controllers that can be a fourth the fucking size and still accomodate all the fucking buttons.
