I was thinking the other day how many controllers I've used over the years for each system. Picking a fave is not easy as most have done their job based on the device and games it was intended for. Thought I'd pick out a few that I've used over the years but tough to choose which is best overall.
PS1 pad was amazing for its time and influential for many years to come. Loved the D-pad and buttons. Start and select were a bit weird to press but it did the job perfectly.
N64 was very advanced at the time especially with the 3D stick, a solid D-pad, shoulder buttons, Z-trigger along with the two standard plus yellow directional ones. Didn't use the d-pad much from what I remember but the 8-direction stick was really ideal for the likes of Goldeneye and the array of platformers.
Dreamcast controller was pretty awesome - fit nicely in the hands and much smaller than it appeared in pictures. Full 360 degree stick with solid grips too. D-pad was a bit too tight and raised for my liking though but was fairly under-used in most games plus the coloured buttons also felt a bit cheap. The VMU/memory card aspect was also pretty interesting but devs didn't make much use out of it in the end sadly.
Microsoft Sidewinder - got this for Christmas around the early 2000's. Bit weird on the face of it but it worked surprisingly well. Had a strange 3D-type D-pad that was slanted slightly which was fairly unique even to this day. My only gripe was the lack of coloured or clearly marked buttons. Very comfrotable though.
Playstation 2 pad was just amazing - expanded upon the original with pressure-sensitive buttons and twin sticks - these didn't have much grip and were perhaps a bit large but they worked pretty well.
The first Xbox pad was way too heavy for my linking - I didn't really like the white and black buttons as they were too small and dug into your finger. The vibration also made a buzzing sound and the coloured buttons felt a little elevated and cheap. Can't remember how the D-pad was but the sticks were solid enough. Seemed a little over-engineered but with tweaks, future Xbox ones were spot-on.
Gamecube controller was very strange - every button was bizarre and the D-pad and right stick was just so oddly placed. It didn't really have a detrimental effect on the games and the main 3D stick was fine but it just seemed a bit of a mess.
I don't quite consider the Wii, 360 or DS3 pads retro as of yet - all excellent and highly reliable controllers. The Wii was really unique in what was a bit of a fad of the era despite monumental success. The 360 and PS3 controllers were both excellent and remain the key foundations for pads today.