I think I'd have to say the Gamecube had the best controller. The analog sticks were very tight and responsive, the button layout was great, and while the D-pad was pathetically small I never used it much anyway (besides, it was very responsive as well, it's just that a grown man's thumb would easily eclipse the whole thing). The Xbox controller S is a close second though.
I have to call out some of the controllers people are listing though. IMO the dualshock 1 and 2 are two of the least ergonomic controllers I have ever held. The shoulder buttons are a pain in the ass to reach and the placement of the analog sticks leaves a lot to be desired. Speaking of the analog sticks, they're also some of the loosest and most clunky sticks on any controller. I will, however, give ipraise the D-pad since it's one of the best out there.
The worst controller though (ignoring fringe systems and pre-NES systems) has to be the Saturn analog controller. The analog stick is without a doubt the worst analog stick ever made (more like an analog nub) and the design of the controller is pretty much a disc with two plastic rectangles glued on the bottom. And let's not forget the crappy D-pad that makes the Xbox 360's D-pad feel like the dualshock's. The Dreamcast's controller isn't much better since it's essentially the same controller except with two less buttons, a better d-pad, a better analog stick, and a slightly more ergonomic design.
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