The dualshock controllers have always been my preference, along with the Dreamcast controllers. I can't play things like Devil May Cry without a PS2/3 controller. No matter how much time I spend with other stuff, it just never feels right.
The Dreamcast had an excellent and super cheap (comparably) arcade stick but I found the standard controller to be dreadful. It invented analog triggers (afaik) which was important and amazing, but the general shape was terrible to hold and the buttons super flimsy IMO. Visual Memory cards were a cool idea on paper but the execution was pretty terrible too and it ended up being just a needless feature that increased the price of official memory cards.
I think the PS2 era dual shocks were probably the best Sony controllers, though the Xbox 360 controllers might actually be better in general as long as you don't need a dpad. The PS3 dual shocks were sadly IMO a step back from the PS2 ones, with the analog L2/R2 buttons that had this really terrible angle. Also not a fan of the pressure sensitivity of the shape buttons on the PS2/3 controllers, it always got terribly finnicky when games actually used that for distinguishing different actions (I have bad memories about some MGS game using that for close quarter combat, it was a mess).
Worst controller of all time? Wii U tablet