#2 The Undertaker vs. Shane McMahon – Hell in a Cell – WrestleMania 32
This might not be the longest HIAC by time, but it certainly went on for an eternity. That’s because the in-ring action was so boring, especially compared to previous HIAC matches. The problem here was that WWE once again wanted to promote Shane as a capable wrestler, despite not being anywhere near a wrestling ring for years.
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Yet fans were expected to believe that Shane was credible enough to beat ‘Taker at WrestleMania, which is a feat that only the freakish Brock Lesnar could do. Shane’s offense in the entire match was so unbelievable and unrealistic that the match’s booking almost required some kind of outside interference to make it watchable.
That would’ve been the perfect way to make the story of this match more interesting, and WWE could’ve booked one of many wrestlers to interfere on Shane’s behalf. Alas, no one came, and the match progressed at a snail’s pace until Shane did the one thing he’s actually good at, jumping off high places.
That jump off the top of the cell all but saved this match from being a complete snooze-fest and was one of those ‘moments’ WWE loves to make (often at the expense of match quality and storytelling).
So while this isn’t the worst Undertaker WrestleMania match, it is arguably his most disappointing, as it could’ve been so much better with the simplest booking changes.