I've played an Atari Jaguar before. Those controllers were fucking awful.

The 64 controller is a close contender, although it's hard to give it shit when it was from when 3D first started being a thing and nobody really figured shit out. But I mean, it should have been a no brainer to not design it so you'd need 3 hands to comfortably use all the inputs.

If you mean specific brands and what not; I can't even remember all the garbage 3rd party things I've used throughout my life. Not good enough or terrible enough to even remember.