George W. Bush (Will Ferrell)
Ferrell put so much dimensionality into his fratboy-ish Dubya performance that he often did a better job selling Bush's humanity than the President himself. Yes, the show once portrayed our 43rd president as being easily distracted by a ball of string. But damned if didn't Ferrell's Decider-in-Chief didn't always try his best to overcome his experiential shortcomings. It wasn't as savage as some viewers might have hoped, or as many thought that the man who lead us into two wars and a near-economic collapse deserved – though we'll point you to this sketch from 2000, in which the show envisioned a possible Bush 43 future characterized by him breaking the Hoover dam and California had become, under his watch, a detached "New Iraq." Ouch.