This is tough...
1: 3DO - Will not f*cking do diagonals, requires 20 lbs of force just to register a direction, not enough buttons for its time
2: Jag - Just...shit
3: Anything else Atari. My god, for practically inventing games as we know them they sure didn't understand controllers very well. The 2600 was like some kind of strength training device.
4: Dreamcast - Sure, it looks like the NiGHTS pad, but its actually total shit. Buttons are tiny. d-pad is ASYMMETRICAL (WHAT THE f*ck!?) analog stick has a dead spot in it representing a full %25 of its travel, missing two face buttons (as compared to NiGHTS pad), cable exits the bottom (again, WTF?) and by far the worst part, the basic shape of the thing forces your hands in this f*cked up position where your thumbs actually have to point away from the center. This is still a way better controller than the 3DO, for example, but after the Saturn its a huge WHAT THE f*ck device. I so so love LOVE the Dreamcast, but f*ck this controller.
5: Intellivision