It wasn't a traditional heel vs. face feud, but that's okay. They did enough to warrant this top spot thanks to an incredible story that saw them end it on the grandest stage of them all. They had a great rivalry in late 1997 and early 1998. Then Michaels was forced to retire in 1998 due to a back injury. When Michaels came back in 2002, he was a Raw guy while Undertaker was a Smackdown guy and they didn't really cross paths until the 2007 Royal Rumble. That's when their awesome chemistry returned as the final two guys in the Royal Rumble that was won by Undertaker. It was the best final two matchup in Royal Rumble history. It also left us wanting more. When they met at WrestleMania 25 in 2009 it was as if we hadn't seen them compete before. It felt so fresh. It was fitting that these two legends were meeting at the 25th WrestleMania. Their match is, in my opinion, the best match in WWE history. There were no stipulations on the match. It was simply a wrestling match. It featured so many amazing nearfalls and it just worked on so many levels. Every time it looked like Undertaker had it won, Michaels found a way to kick out. Then Undertaker caught Michaels after a moonsault and Undertaker planted him with a Tombstone to win it. Michaels wanted a rematch the next year, but Undertaker was reluctant to do it. Unfortunately the rest of the feud happened in 2010, which was the end of the 2000s so because of that technicality it's not higher on this list.
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.
