#2. Triple H
Our number two spot belongs to the Cerebral Assassin, the Game, the King of Kings, the current COO of WWE, Jean Paul Levesque aka Triple H.
Triple H has managed to rack up an impressive six wins in the Hell in a Cell Match. In fact, he has more Hell in a Cell appearances than any other superstar except for one. While many may point to Triple H's obvious backstage connections as the reason for his many victories, one must also remember that after the Attitude Era ended, the Rock left and Stone Cold Steve Austin was no longer an active wrestler.
This left Triple H as the biggest name star in the company, and a logical choice for the pay-per-view main events in which Hell in a Cell matches often take place. His success inside the heinous structure is one the reasons why he has lived up to his 'Cerebral Assassin' moniker.