-Duke OG Xbox controller is really oversized, it's almost bigger than my hands and i can't even reach push black/white button with my thumb.

-Dualshock 1, 2, 3 and 4's d-pad is painful, so instead i control with analog stick.

-N64 controller's analog stick is highly painful, it could damage your thumbs when you play the game a LOT.

BONUS Fact: Did you know N64 gamers were forced to buy aftermarket controllers because the wrong holding way grip and plastic analog stick?

^They were holding wrong way grip like this.

^No more damaging your thumbs.

^The best solution and expensive.

I've always held the N64 controller in the correct way, but it never felt right to me because my hands felt cramped. Overall though my biggest problem with the N64 is not really its awkward shape but the analog stick.

I'm suprised to see so many people listing the PS controllers, my hands are quite large but I've always found those controllers to be comfortable. While in contrast I've found the 360 controller to be less comfortable because of the battery pack rubbing against my fingers. Love both controllers regardless.

N64, original Xbox and Dreamcast.

Same.

Out of all of those I'd have to say the Dualshock 3. It was just very cheaply made imo and I didnt enjoy my experience at all with it.

I don't think it's the worst but the difference between PS3 and PS4 controllers is like night and day, I can never go back.

The Dualshock line on Playstation consoles. Wat too small and tight for my big hands. Plus, to this day, I have a hard time with the square/circle/triangle/cross button layout, ABXY is soooooo much easier to my mind. Though haven't tried the DS4 yet, so I leave that one out for now.

Otherwise, a third party Joystick for the Sega Master System called the NaviGator. It also works on other machines with the same connector like the VCS, and that's probably how it ended up with just one single button - and autofire.

Than I'll add the GBA-SP. Wayyyy to tiny for me. Didn't even want to try out the Micro after playing on that one, going back to my original Advance instead.

Actually the Sega Master System controller wasn't that bad it was just vastly inferior to the NES controller and its built quality and durability where on the poor side compared to the NES controller which is one of the most durable controllers ever build. As far as worst controllers it has to be the N64 controllers and all Atari system controllers they where all poorly designed and not very durable the worst out of those is probably the Atari 5200 controller.

Not the worst maybe this a good place to complain about the D-pad of the Switch pro controller. Everytime I press left or right, it presses up. Ugh.

My least favorite controllers in order (least favorite being first):
-Pretty much anything before gen 6
-A cheap third-party generic dualshock-like thing for my PC
-Wii Classic Controller
-Xbox Duke Controller

My favorite controllers (in order from best to worst):
-Dualshock 4 and Wii U Gamepad tied (I hate the stick positioning on DS4, I hate the lack of analog triggers on Gamepad)
-Joy-Cons (dislike that there are no analog triggers and audio jack; but love the versatility)
-Switch Pro controller and Xbox 360 controller (dislike lack of analog triggers and audio jack in Switch Pro controller; dislike terrible d-pad and lack of motion controls).
-Wii U Pro controller and original Xbox One controller and Xbox One Elite controller (none have motion controls; lack of audio jack and analog triggers on Wii U Pro bothers me; the stiff shoulder buttons and lack of rechargeable batteries is annoying on the Xbox One's original controller; the XOne Elite controller has a really unresponsive dpad and still no rechargeable batteries).
-Steam Controller (best controller for aiming; but not good for a lot of other things)
-GC controller