It was the 25th anniversary of WrestleMania and one of the most anticipated matches on the card was themed as “The light vs The dark”. It was Shawn Michaels vs The Undertaker, competing against one another for the first time at WrestleMania. They were no strangers to each other, but it had been a long time since they last crossed paths.
The last major moment where the two crossed paths was over 11 years prior, and it happened to be in the first ever Hell in a Cell match. Bad Blood 1997 saw The Phenom challenge Shawn Michaels, with the winner getting to face then-WWF Champion Bret Hart at Survivor Series 1997, the infamous Montreal Screwjob event.
They would have an all-time classic, and till date, many consider it to be the single greatest Hell in a Cell match. The most notable thing about the match was the fact that it saw the debut of Kane. That too is considered by many to be the single greatest debut in WWE history. However, that was 1997, and we’re jumping ahead to over 11 years later.
Things were very different between the two by this point. Both of them had come a long way. For one, a few months after his classic encounter at Hell in a Cell, Shawn Michaels lost the WWE Championship in the main event of WrestleMania 14 and would officially retire from competition due to back injuries.
By that time, The Undertaker had continued to cement his legacy and extend his WrestleMania streak. A few years after, he would adopt a biker gimmick for a while before eventually switching back to the character that made him famous in the first place – The Deadman. He would become an integral part of SmackDown in the Ruthless Aggression Era, where he was a mainstay and would work with a newer crop of talent than the one he had before.
Come 2009, Shawn Michaels nor The Undertaker were really doing as much as they should have from a championship perspective. He came close to winning the WWE Championship at Elimination Chamber, but fell short to Triple H, the man who would headling WrestleMania 25 that year.
As a result of this, it seemed to be the perfect time for Shawn Michaels and The Undertaker to cross paths with one another. Michaels had to get through JBL and even Vladimir Kozlov to earn a shot against The Undertaker at WrestleMania 25. It speaks volumes about how prestigious The Undertaker matches at WrestleMania were when superstars had to compete to face him as though it was a title match. It was similar in 2013, when CM Punk defeated multiple competitors to earn the right to face The Undertaker at WrestleMania.
The Undertaker was always the kind of character who never really needed a title, but his WrestleMania streak was so prestigious, mythical and was such a draw, that it was often viewed bigger than any other championship match on the card. And in 2009, there was no match on the card bigger than The Undertaker vs Shawn Michaels.
The build saw the two play some real mind games with each other, and it was set to be an exciting battle between two legends of the business. The day would come, and fans were on the edge of their seats. Shawn Michaels entered from above, descending below, representing the “light”, while Undertaker entered from below the stage, representing the “dark”.
When the bell rang, the two wasted no time in getting started. It began with a fast pace, and it went on that way, with the two somehow managing to maintain an incredible work rate throughout the match. The Undertaker nearly had a freak accident when a stunt double cameraman failed to catch him, but he managed to work through it successfully.
Ultimately, what made the match great was that it was a simple, straightforward affair that saw two legends use around two decades of knowledge in the ring and place it in the ring for the world to see. In a way, it was a culmination of their skills and talent and experience that they developed over the years, and it translated beautifully in the ring.
It’s viewed as by many as the greatest WrestleMania match of all time, and for good reason. It was voted the match of the year in WWE, and Shawn Michaels came seconds close to ending the streak on more than one occasion. The heart that he displayed was unlike anything before, and The Undertaker’s facial expressions said it all.
All in all, it was a masterful piece of storytelling and WWE knew that they had to run it back the next year, with the match being the one that ended Shawn Michaels’ storied career.