3. Big Boss Man
YoutubeIt's probably the worst Hell in a Cell match ever with an ending that we all want to forget. When fans think about the Undertaker's great matches at WrestleMania this one at WM15 is one they shouldn't remember because it was awful. It was a heel vs. heel match. Those rarely work out well. By this point in his career, the Big Boss Man served a purpose as a security guy for Vince McMahon. He really wasn't in a position where he should have been in a Hell in a Cell match with somebody of The Undertaker's caliber. Nobody believed that he had a shot to win before the match or during the match, so it took the drama out of it immediately. The crowd was so dead for this match. Nobody cared. It wasn't interesting either. Undertaker won with the Tombstone and it was the first time that there was any kind of reaction. When it was over, Undertaker got the help of the Brood and they hung Bossman from a rope. The camera cut away, then it was completely ignored and we had to just move on from a guy hanging in the ring. Brutal.