#6 Shane McMahon’s infamous drop (Hell in a Cell match, 2016)
At WrestleMania 32, Shane McMahon competed in a high-stakes Hell in a Cell match against The Undertaker. The Phenom dominated most of the match, while Shane heavily relied on weapons to gain the upper hand. At one point, The Undertaker slammed Shane through the side of the cell and both superstars crashed onto the floor at ringside.
Following that, Shane McMahon hit The Undertaker with monitors and toolboxes to keep him down. He put ‘Taker on the announce desk and climbed onto the top of the Cell. Shane then attempted Leap of Faith from the top, but his plan backfired. The Undertaker moved, and Shane McMahon crashed into the announce desk. Although Shane McMahon lost the match and left the arena on a stretcher, this risky Hell in a Cell spot earned him a lot of admiration.
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#5 End of an Era (Hell in a Cell match, 2012)
Another of The Undertaker’s Hell in a Cell matches was at WrestleMania 28. He faced Triple H in one of the most memorable matches of his career, widely known as End of an Era. Shawn Michaels also played a critical role in the match as a special guest referee. It was an instant classic as both Undertaker, and Triple H risked everything to deliver a blockbuster.
At one point in the match, both Michaels and Triple H teamed up to brutalize Undertaker. The Deadman would take a lot of punishment as he was subjected to a never-ending series of Pedigrees, a Sweet Chin Music, and multiple chair and sledgehammer shots. He was bleeding profusely but kept coming back for a fight. ‘Taker eventually used a few devastating Tombstone Piledrivers to win this Hell in a Cell match and extend his WrestleMania streak to 20-0.
Fans gave them a standing ovation after a brilliant display of action and crafty storytelling. Following the match, Undertaker and Shawn Michaels helped Triple H walk back. The three superstars then hugged near the entrance amidst WWE Universe’s thunderous applause. This Hell in a Cell match became a bittersweet reminder of how the superstars of yesteryear went to war inside the squared circle.