#1 Kurt Angle (King of the Ring 2001)
What's tougher than wrestling twice in one night? Wrestling three times of course! And what's tougher than that? Having one of those matches be a Street Fight.
But at the 2001 King of the Ring, Kurt Angle did just that, first meeting Christian in the semi-finals of the titular tournament, where he was assisted by the man he would meet later that night, Shane McMahon.
It was the same Shane McMahon, who ended up costing Kurt in the KOTR finals against Edge, revealing how he had only helped Kurt in the semis, to force the Olympian to exert more energy.
Rightly peeved, Angle waged a war against Shane-O-Mac in their Greenwich street fight, throwing the Prodigal Son through a glass pane, and whilst Shane gave a valiant fight, it was Angle who emerged the victor. Oh, it's true!