Old favorite of mine was the 360 controller. Everything about it was perfect except the D-pad, which was outright horrible.
The Xbox one S Controller is my all time favorite one at the moment. Controllers really is the only thing Microsoft does right and I use it for most games on my PC. The stick is nice and on the right location, They fixed the issues with the shoulder buttons, and the D-pad, which works perfectly for when I play a 2D platformer, It has nice analogue trigger buttons for the games that require it (something Nintendo refuses to do for some reason after this first Classic controller) and everything is just as it should be. I'm not a guy that cares much for the gimmicky stuff like rumble and motion controls so that doesn't factor in for me personally.
The Cube controller is another one of my favorites, mostly because of the shape of the face buttons. I'd like to see another controller try something like this. Its a shame it lacks buttons and has a terrible D-pad, so I only use it for smash nowadays.
PS controllers I never cared for because of the meh D-pad and the location of the left stick, but the build quality of the ps4 one felt nice.
Nintendo has been dropping the controller ball ever since the wii for me. wiimote sideways felt terrible to hold and dragged down any game that insisted on using it for me, with nunchuck was a bit better but it lacked buttons and im not too big on motion controls. The classic controller was alright, but having to connect it to a wiimote to play really was bad design.
The gamepad felt way too big and was dead after 2 or 3 hours of gametime. almost no game made good use of the gamepad screen so there was no reason (other than price) to just use the wii U pro controller, which is probably the best controller they made in a good while. I don't like the glossy finish but its battery life was massive, felt pretty light, and buttons were all good quality. After 1000 hours of Monster hunters and other games my left stick has a bit of issue and I need to blow in it occasionally to fix it but otherwise its great.
The Joycons are probably one of the worst they made, they feel cheap, small, and the button quality and layout feels terrible. Everytime the sticks make that cheap sounding metallic kinda noise I shudder. The faults are understandable because they pushed the "you can play multiplayer with each player just using one joycon!" thing but it was not worth it for me. Every time I switch to the Switch pro controller I feel both my performance and enjoyment greatly increasing. One among other reasons I never really use handheld mode.
The pro controller is great but feels a bit on the heavy side, and the 60/70 bucks price tag is a bit hefty. And I can understand not wanting to pay that much for a controller that can't even get the D-pad right. Somehow they screwed that up even though Nintendo is usually pretty good/decent at making a useable D-pad The xenoblade edition improved it but its still not perfect. The rest of the controller is fine though.
The steam controller is an oddball though. They tried to make games that were only seen as "mouse and keyboard games" (think First person shooters or other first person games, and strategy games) playable on a real controller, but It ended up being a 50 buck middle ground that wasn't really better than mouse and keyboard at mouse and keyboard games, and also not as great at controller games than most other controllers, due to pretty bad button placement, and no D-pad.
Great thread