the PSX dual Shock is bad, the layout is a rip of of the Snes controller (not a bad thing), but the new R2 and L2 shoulder buttons are a bit awkward. that's not the worst part, that being the actual analog sticks are hard to use (for me, my hands are pretty small), and make the shoulder buttons even harder to use. they also get in the way of the start button.
the (you'll hate this) ........ Sega Genesis Controller was also difficult to use. having 3 large buttons on the thing, and moving my thumb from A to C, during normal gameplay that needs it done as fast as you can, was difficult, and wore out my thumb in half an hour. the 6 button controller was a little better (with smaller buttons), but the extra 3 buttons made it worse overall. for Sonic games, that wasn't noticable, and for RPG's it never mattered.
these are far less awkward than that ColecoVision controller (who the heck designed that cruddy thing?), or the Jaguar.
never tried Xbox, GCN, or Dreamcast controllers (though the latter looks like a descent controller)