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411’s WWE Rivals Report: Shawn Michaels vs. The Undertaker

March 10, 2024 | Posted by Robert Leighty Jr.
Shawn Michaels Undertaker WWE WrestleMania Image Credit: WWE

-I got to this one a little late as I was wrapped up in watching The Oscars. This one should be fun, and not just because I was there to see two of these matches. Let’s get to it!

-Freddie Prinze Jr is the host and creator of this show and is joined at The Table this week by Cody Rhodes, JBL, Kevin Nash, and Beth Phoenix. Cody calls Taker the last, true locker room leader.

-We jump back to Survivor Series 1990 where The Undertaker famously made his debut. Taker himself says he spent the early 90s trying to figure out what The Undertaker character is. He was trying all kinds of things and seeing what worked. Kane says it should have been cartoon like, but it became cool creepy.

-Shawn Michaels notes that it was a cool character when Taker came in, but they wondered how long that would last. They weren’t sure it would have a long shelf-life with the no selling and idea he was dead. Taker says he dropped some of the sillier things but kept enough to make people believe in the character.

-Cody talks about the natural progression from being afraid of Taker to respecting him and loving him. JBL says Undertaker was the cornerstone of WWE through the good times and bad times.

-Now to Shawn Michaels, the best in ring performer of the time. Steve Austin puts over the type of in ring performer that Shawn is. Taker calls him a pretty boy that was ahead of his time and he could work with a broomstick for 30 minutes and make it entertaining.

-Michael Hayes says Shawn was great, but make no mistake about it, he was a PRICK. Awesome! Taker says back then he and Shawn were different, and they both agreed they didn’t like each other. We see some of the juvenile stuff he did on camera, and it was probably worse off, but he was so great in the ring that they let him get away with a lot of stuff.

-SummerSlam 1997: WWF Champion, Undertaker vs. Bret Hart with Shawn Michaels as the special ref. You can find my review here. Bret spits on Shawn, so he swings for the fences with a chair and accidentally hits Taker. Bret gets the win and The WWF Title, but Shawn/Taker is now the hottest program in the company and Bret on the under-card while Shawn and Taker headline back to back PPVs.

-Taker: “Back then I would not have pissed on Shawn if he was on fire.” Fantastic! He does say there is nobody he would rather be in the ring working against.

-Ground Zero: Sept 7, 1997: My review is here. It’s the first one on one match between Shawn and Taker. Shawn says they could feel the comfort when they locked up the first time, and they knew instantly they had something. Shawn against big dudes is always a winning formula, but when you give him a skilled big dude, magic happens.

-Commercials!

-Back to Ground Zero as they fight all over the place and there is no winner, but Taker dives over the top rope onto a crowd of heels to pop the crowd. The story became that Shawn was doing everything he could to get away from The Undertaker, so they needed something to contain him.

-Badd Blood: Oct. 5, 1997: The very first Hell in a Cell Match! My review is here! Shawn says this was his version of Christmas. Man, how does he celebrate New Years? Just a perfect match and still the greatest Cell Match of all time. Taker: “I beat him like he owed me money.” Again, the match was basically a horror movie come to life as it was Shawn doing all he could to survive. The way they used the injured camera man to get the action out of the cage was genius. Then Shawn gets desperate and climbs the cell to escape and the crowd explodes. Go watch the match again after this review. Taker brings up the camera shot from below where Shawn’s blood was dripping down and onto the camera. Shawn then falls off the side and through the announce table. Somewhere, Mick Foley says I can top that!

-Kane then makes his debut and he says the match was so great, he was worried his appearance would mess it up. It didn’t! Kane hits Taker with a Tombstone and a bloody Shawn, crawls over for the pin and becomes number one contender for Bret’s WWF Title at Survivor Series. As we know, nothing of importance happened there.

-Royal Rumble 1998: I haven’t reviewed that show yet, as I jumped back to 1989. This is a Casket Match for the WWF Title as Shawn is now the champion. It was more of Shawn getting his ass handed to him and Shawn discusses the psychology of how it did nothing for his character to just beat Taker without help. That brings out Kane again and Shawn gets another win by the skin of his teeth.

-The bad part of the match: Shawn destroys his back taking a backdrop over the top while trying to clear the casket. Taker notes that he wasn’t sure how hurt Shawn was because of his past issues. Yeah, we know what he means. That whole losing his smile thing. Shawn says he crushed several discs in his back and he had to get his lower back fused.

-Commercials!

-Nash says that when Shawn destroyed his back, he was done. Taker on the other hand continues to roll and beat opponent after opponent at WrestleMania. Taker says he didn’t know there was a streak until WrestleMania X-8 when he beat Flair to get to 10-0.

-SummerSlam 2002: A few months later, Shawn Michaels makes his return and is a new person. Shawn found Christ and made changes in his life. Taker says he welcomed Shawn back, and Shawn apologized for being a prick. They found common ground and became friends while bonding over the fact they were the two through ups and downs in the WWF that stuck around. They were seen as pillars.

-Royal Rumble 2007: Shawn and Taker are the last two men in the Rumble and basically have a mini match that nearly stole the show. I believe this was the same show as Cena/Umaga in their classic Last Man Standing Match, and that really stole the show. What Shawn/Taker proved though is they were still magic and people still wanted to see them wrestle each other. Taker gets the win and goes to WrestleMania where he challenged Batista. Funny enough, he didn’t get to close the show as Cena/Shawn got the honor.

-Michael Hayes brings up how there was never anything conclusive in their 3 matches in the 90s as they had a no contest, and then Shawn winning the next two thanks to Kane. The story became Mr. WrestleMania vs. The Streak and you didn’t have to say much to convince Shawn or Taker.

-We get highlights of Shawn at WrestleMania and JBL brings up that Shawn is 6-11 at Mania but still had the name Mr. WrestleMania. “When you are that good, you can get beat and nobody remembers it.” The promo work leading up to WrestleMania XXV was tremendous including Shawn dressed like Taker, but in all white.

-WrestleMania XXV: I WAS THERE! My first WrestleMania that I attended. Houston was wonderful, and them showing video of the city takes me back. Here is my review of that show. Taker says Hayes was their producer and Taker wanted to know where they were on the card. Hayes says he was trying to keep that quiet for as long as possible and then he tells them they are on 5th. Taker and Shawn are silent as they realize they are 5th on a show with 10 matches. Shawn and Taker understood it didn’t need to be The Main Event, but it needed to be near there. Shawn: “Well, now they are fucked. We are fixing to tear some shit down. We are going to burn this motherfucker down, so just end this show. Who is going to be able to follow it.” Poor HHH!

-As mentioned, I was there live and it is still the Greatest Match I have ever seen live. JR said it perfectly on commentary about it causing an out of body experience. Taker dives over the top and Shawn pulls the camera man in the way (call back to Hell in a Cell) and Taker nearly breaks his neck.

-Commercials!

-Back to Taker spiking himself on the floor. Beth says she was watching on the monitor and everyone gasped seeing Taker splat like that. Taker says Shawn was to push the camera man in the way, but the camera man wasn’t there and Shawn tried to pull him in late. Taker says he got his bell rung and didn’t know where he was at for a second. Shawn knew Taker was okay because he could see that he was pissed. Taker could hear the count and realized he needed to get in the ring. One of the best reactions ever to a tease of a count-out.

-The match just builds and builds to a fever pitch as the Stadium was rocking. Cena puts over Shawn’s timing as being better than perfect. “You can perform with him forever.” These near falls are getting me fired up right now. Then the Skin The Cat into a TOMBSTONE for one of the greatest near falls you will ever see. The place went insane on that spot. HHH says he was working with Randy, and saw most Shawn/Taker and realized, “we are fucked.” No kidding! Taker gets one last Tombstone and goes to 17-0. I watched as people were hugging and some were crying around me as that match ended.

-JBL: “I’m glad I retired because that was the greatest wrestling match I ever saw.” Shawn left that match with peace and told his wife that maybe he should retire on that one. He says that match helped him confirm he wanted to retire and now it was a matter of getting there.

-Slammy Awards: Dec 2009: Shawn accepts Slammy for Match of The Year and throws out a challenge to Taker for one more WrestleMania Match. They skip a lot of the story of Taker refusing until Shawn cost him the World Title and jump to Taker accepting in Feb of 2010, with the stipulation being that Shawn’s career is on the line.

-Commercials!

-Shawn: “If I can’t beat you at WrestleMania, I have no career.” So it became Streak vs. Career. Taker says the pressure builds as he was responsible for someone like Shawn’s last match. Shawn apparently had the idea for the match at 3 AM, called Hayes and wrote everything down.

-WrestleMania XXVI: I was there for this one too! Review! I enjoyed Arizona more than Houston the year before and Atlanta the next year. Just being in a resort in the middle of a desert was sweet! Best show top to bottom of the three I attended as well. This time they didn’t make the mistake of having anyone follow them. Another amazing match, that could never top what they did the year before, but it’s still amazing and is the second best match I have ever seen live. Cody says he doesn’t think of them as separate matches and they were just one long story. Shawn is beaten, but won’t stay down and slaps Taker in the face in one last act of defiance. Shawn says he wanted to go out poetic and HBK would demand to be beaten like a man. SLAP!

-Commercials!

-Beth notes that if you watch a Shawn match, you can see the art of what they do. Taker gives Shawn a SUPER JUMPING TOMBSTONE to go to 18-0 and end the career of Shawn Michaels. Taker talks about how emotional it was and how he knew it was the last time he would be in the ring with this talent and his friend (ehh, unfortunately no, but we will just say the Saudi show is non canon).

-Cool moment as they show Taker watching backstage as Shawn takes his leave one last time and then they embrace backstage. That’s awesome! HHH and Vince are there giving them a standing ovation and it looks like they both have tears in their eyes. Hayes embraces Shawn and he has tears in his eyes as he thanks Shawn for letting him do it. More great stuff as Shawn is with his family and Taker notes that Shawn’s daughter is giving him the evil eye. This is making me smile!

-JBL wonders what history would have missed if Shawn and Taker never crossed paths. Foley says both men came through big when the spotlight was the brightest.

-We jump to Taker being inducted to The Hall of Fame and greeting Shawn before the show. He also thanks Michaels during his speech. We close with them face to face over the years, and one last image of them hugging at the close of their Mania XXVI match.

-This was wonderful and it will be hard to top a 5 Match history like they had. I was lucky enough to be there for the last two, and Hell in a Cell I is one of the most famous matches of all time that launched an iconic match type that endures over twenty-five years later. Definitely worth a watch and it’s never a bad idea to go back and watch the five matches they had against each other. Thanks for reading!

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WWE Rivals, Robert Leighty Jr.