1. PlayStation 2 DualShock

Pros: The pinnacle of controller design that borrowed from its previous ancestors, it still stands tall as the culmination of years of hardware trial and error.
Cons: The wire—especially compared to the Alaskan Pipeline that was the SNES controller—was too short. And it didn’t pop out of the port easily if someone tripped on it or you pulled it accidentally, which meant that if the PS2 was on a shelf, it was crashy crashy time.