10 Biggest Ever Heel Vs. Heel WWE Matches

4. The Undertaker Vs. Big Bossman - WrestleMania 15

A lot of people remember this match as the worst Hell in a Cell match in WWE history. It was also arguably the second biggest match at WrestleMania 15 and it involved two heels with The Undertaker taking on the Big Bossman. This was during the point in Undertaker's career where he became more of an evil, demonic heel that convinced people to follow him and do work for him. They called it the Ministry of Darkness. They had him do all kinds of crazy things like tying Steve Austin to a cross and also what he did to end this match: hanging Big Bossman by a noose. Undertaker won the match clean. It was boring. Post match, the Brood showed up to tie Bossman, then Undertaker hung him and they just moved on from them. It's pretty crazy that a wrestling show would go so far as to have somebody hang from a noose as if that was some great idea, but that's what happened. Looking back, it was such a stupid angle and also ridiculous that they barely paid attention to the sight of a grown man on the receiving end of a hanging like that.
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John wrote at WhatCulture from December 2013 to December 2015. It was fun, but it's over for now. Follow him on Twitter @johnreport. You can also send an email to mrjohncanton@gmail.com with any questions or comments as well.