The Video Game Critic

For consoles that I've played, here is my list:

Best-
Wii U Pro Controller- feels great and very responsive.
Sega Saturn 2 controller- probably my favorite controller that lacks an analog stick. Very comfortable and miles better then the original Saturn controller.
Xbox Controller S (Original Xbox)- excellent controller that is a much better size and the changed button layout helped drastically.

Worst-
Colecovision- God I hated this controller. The stick is so stiff I was afraid I'd break it. Thank god you could hook in a Sega Genesis controller to the Colecovision.
Atari XEGS control stick- absolutely terrible. So stiff compared to the original 2600. I don't know how Atari messed it up.
Jaguar- While it has some redeeming qualities the controller is so stiff and bulky everything just feels awkward. I even have pretty big hands and I feel this way. Not the worst, but deserves a mention.

Mine would be a tie between the GameCube controller and the Jaguar controller. Aside from the numeric pad, I really like how the Jaguar controller feels in my hands. It reminds me of the Wii U tablet, actually...

Most comfortable: NES dogbone.

I've never gotten a hang of all the post-SNES controllers where you have to contort your hand in order to operate these "Shoulder Buttons." I'm not a fan of the crab hands!

The NES controller was pretty basic, but had a great D-pad. The dogbone pumped some ergonomics into the old girl.

Least favorite? Gamecube. It's like someone squished an N64 controller into 2 pieces (instead of three), and randomly skewed buttons across the controller.

Good controllers The Atari Jaguar controller, the pro controller (7800) the 2600 controller, the megadrive controller, Snes (a joy to use)  the ps1 (dual shock) all the xbox controllers.  I rather liked the n64 controllers as well. The konix controller for the zx spectrum.

Not so keen on it Master system, gamecube wii  nanchuck controller.

The controller that needed to be spot on as it is essentially Intellivision, Colecovision and gamestick.  Not great controllers. 

Least fave.  The original quickshot controller from spectravision for the 2600 and could be used on the ZX spectrum.  The thing was so bad as it was unreliable. 

PlayStation controllers all suck except for the PSP,...all of them are too small,and the d-pad pinches my skin. It's like the SNES controller was shrunken up and bastardized.

Not a fan of the Atari 7800 controllers either.

Nintendo controllers and all the non-Master System Sega controllers seem to be very comfortable, the N64 is the only truly good one for my hands (Dreamcast ,and Xbox Duke are almost there,but the D-Pads are too small and there isn't the same lightweight and roomy feel on the underside of either), the GameCube is the only small controller that attempts decent grips and probably has the best grooved thumbstick. The Saturn 1 controller has the most flexible D-Pad known to man.

The GameCube is easily the most comfortable to me.

I could put the Wii-mote for both good and bad. Some games it is superb and works like a charm, others I find it immensely frustrating and wish I could just use a traditional controller. Likewise with the PS3 six axis nonsense.

Also the Channel F controllers are great ! You need to try these things in fact I'd put it out there as the best 2nd Gen controller.

@Astrosmasher - I used a Cheetah Joysticks back in the day with my Speccy and thought they where great. Until I moved onto my ST with a better joystick, when I replayed my Spectrum it felt like the Cheetah would come apart in my hands. Will have to look out for the Konix, although I'm using an Amstrad GX4000 gamepad through the Kempston adapter now and that works pretty well.