#3 Mr. McMahon
Most fans agree that the Mr. McMahon character portrayed by Vince McMahon during the Attitude Era is one of the greatest heel characters in WWE history. McMahon rarely got in the ring, but if he did, it was to push the other Superstar or help make a feud interesting, as the WWE Chairman was widely hated by the WWE Universe.
One of the Superstars that McMahon stepped in the ring was Brock Lesnar, back in 2003. If that was an insane decision by the WWE Chairman, he decided to make this happen inside a steel cage! Lesnar was in a feud with Kurt Angle as he pursued to win back the WWE Championship, which Angle had won a few weeks earlier.
In the match between Lesnar and McMahon, Angle was the special guest referee, against his wishes. Angle tried to play fair and not help McMahon win, despite the WWE Chairman's overtures. Lesnar, though, doublecrossed Angle and turned heel, siding with McMahon and destroying Angle.
The match between Lesnar and Mr. McMahon ended in a no contest.