For me it all started with the SNES controller. Playstation adapted the major parts of it's layout for their PS1 and has stuck with the key features of that layout ever since. Adding a few extra features such as the L2 and R2 buttons as well as the Analogue Sticks gives us more stuff to play with, but I still prefer using the D-pad.
The Xbox flipped the D-pad and Analogue Stick on the left side, and that decision kept me far away from the Xbox until I felt forced to buy one just to play Alan Wake, which was supposed to be a Xbox 360 only title. Since having played through Alan Wake, Resident Evil 5/6, Dirt 2, Just Cause 2 and bunch of other titles (mostly on the PC), I've gained some respect for the Xbox 360 controller. However, I find it odd and fickle to play games like Street Fighter IV with an Analogue Stick, and the D-pad is just too far our of my thumb's comfortable control-zone to work properly.
The PS3 controller is at the height of it's evolution, in my opinion, and is thereby the best controller.
*****ic concepts like the N64 and Steam Controller is what kills consoles. People look at that stupid contraption they have to hold in their hands and they say "no, thank you".