30 Matches in 30 Days, Day 6: The Undertaker vs. Shawn Michaels, WWE WrestleMania XXV

30 Matches in 30 Days, Day 6: The Undertaker vs. Shawn Michaels, WWE WrestleMania XXV
30 Matches in 30 Days, Day 6: The Undertaker vs. Shawn Michaels, WWE WrestleMania XXV

“Sometimes it’s hell getting to heaven.” - The Undertaker to Shawn Michaels

Click here to watch the match on DailyMotion

Click here to watch the match on the WWE Network

Set the stage

It was december 2008 and Shawn Michaels accepted a deal from JBL to be under his employment. Shawn had lost all his savings due to the global recession and was, in kayfabe, broke. With this contract, he was forced to help JBL in any way that he could whenever he wanted to. This includes having to sacrifice his shot for the WWE World Heavyweight Championship to JBL. During this period and at the Royal Rumble, after JBL promised Shawn a spot in the Royal Rumble if JBL were to win from John Cena, The Undertaker came face to face with Shawn and said “Sometimes it’s hell getting to heaven.”

Safe to say, JBL did not defeat John Cena and JBL was fed up while Shawn wanted to get out of this “employment contract”. If In order to get out of the year long deal, Shawn Michaels had to defeat JBL in a “All or Nothing” match. If JBL were to win, Shawn would still be under contract and receive no payment. If Shawn won, he would get out of the contract but still get paid the whole sum. Shawn Michaels would go on and defeat JBL at No Way Out and thus be making all the money he would be making without having to do a thing (aka living the American dream).

quick note here. I would advise you watch this feud back as well. It is very underrated in my honest opinion and shows some great work from both characters.

Shawn would come out the following night and say he has done it all. He is Mr. WrestleMania. He is the headliner, the showstopper, the main event! He has done it all, except for one thing.

Defeating the Undertaker at WrestleMania.

Shawn respected the Undertaker but he was not afraid of The Undertaker and Shawn would have to earn the honor of facing The Undertaker at WrestleMania 25. The Undertaker would go on to face Vladimir Kozlov on SmackDown where The Undertaker lost after a failed Old School, which cost Undertaker the win. Yes, this happened. Part 1 here and Part 2 here. This was during Vladimir Kozlov’s undefeated streak and they were building heavily on him.

Shawn Michaels would reply to this by ending Vladimir Kozlov’s undefeated streak on RAW about 2 weeks later and Shawn had earned the right to face The Undertaker. With Shawn Michaels wearing white and representing the light and Undertaker wearing black and representing the darkness, this match felt like the true battle between good and evil.

What followed was one of, if not the best WrestleMania match ever, arguably the best WWE match in history.

Where did the story go from here?

After the match, Undertaker would take a break of 4 months until returning to face CM Punk for the World Heavyweight Championship and continue a feud from there on, but the more interesting past would be for Shawn Michaels.

Shawn Michaels would go on and take a hiatus until August when Triple H would find him working as a chef because he “felt like he didn’t need it anymore.” After a bratty child continued to make Shawn’s work as a chef hard, Shawn superkicked the little girl (who was played by his actual daughter) and find his groove to come back and reform DX in its last (and by some called worst) run, including Hornswoggle as a DX Mascot. They would win the WWE Tag Team Championship against Randy Orton’s Legacy (featuring Cody Rhodes and Ted DiBiase jr.) and lose it in february to The Miz and Big Show. During the reign, not only would Shawn Michaels bury the hatchet with Bret Hart but he would also win the “Match of The Year” at the Slammys of that year, where Shawn would, once again, challenge The Undertaker to a match at WrestleMania 26.. The Undertaker declined that offer, at that time still the WWE World Heavyweight Champion. With Undertaker Champion, Shawn would try to get his shot at the Royal Rumble, but failing. Shawn would go beserk and superkick referees as this was all that he had.

After costing The Undertaker the WWE World Heavyweight Championship at the Elimination Chamber by interfering in it, superkicking The Undertaker and letting Chris Jericho steal the win, The Undertaker would accept Shawn’s challenge. If Undertaker won, Shawn would retire and his career would be over. Shawn accepted and both men would meet one more time in the ring, with Shawn Michaels never stepping into the ring actively again.

Why is this match important to me?

From a wrestling point of view, this match has it all. The storytelling in this match is phenomenal. Every little thing they do in that match, they do it for a reason. Not a single moment goes unwasted and every second matters.

From a story point of view, while both men were already considered legends in the world of wrestling, this match proved it once again. They planted the seats earlier, they built up from that, everything just made sense and that’s the match that truely shows that. Storytelling is the greatest factor in wrestling and these guys fucking nailed it.

From a personal standpoint now. When I think of the perfect wrestling match, this match comes into my mind automatically. This is the match that got me into wrestling completely. In the weeks beforehand, I didn’t pay much attention to all of the WWE feuds and sorta nitpicked two or three that I would follow because I was young, and this one was not quite interesting to me. I was more focused at Jeff vs Matt Hardy and after that, in my opinion, disappointing match, I watched Shawn and Undertaker make magic in the ring and get me to truely jump out of my seat.

If a friend of mine asks me what match they should watch, I always pick this one because it’s that damn good to me and truely shows what wrestling is all about.

Pro wrestling at its best.

If I only could...

Be running up that hill...

If I only could...

Be running up that hill...

Possibly the GOAT Wrestlemania match

That was used in the promo package for Undertaker vs Shawn Michaels at WrestleMania 26.. but that is such an amazing package as well.

One of my favorite matches of all-time. Was #1 until the Okada/Omega trilogy.

In my opinion, not the greatest match of all time, but the greatest story ever told in pro wrestling.

Greatest match in the history of wrestling with two of the greatest if not THE greatest men to ever work

Main reason Meltzer's ratings have no weight to me is because of this match

My favourite match of all time without a shadow of doubt

Greatest match of all time imo.

Undertaker's reaction to Shawn kicking out of the Tombstone while Jim Ross yells "I just had an out of body experience!" is probably one of my favourite Mania moments ever.

I know it was 26 and not 25 where that song was used... but to this day, it remains my favourite promo package of all time, and the song will never not make me think of The Undertaker vs Shawn Michaels. Mania 25, Mania 26, doesn't matter to me. This feud made me emotional from day 1 in a way no feud ever has or ever will. Everything about it, the match at Mania 25, the match at Mania 26, the interviews inbetween, the promo packages, the hype on the internet, everything about it was absolutely perfect.