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The Undertaker is officially retired. After 20 years of speculation, it does look like The Undertaker has actually hung them up. Like all wrestling retirements, there is some skepticism that The Undertaker is going to remain retired, but for the time being, one of the most popular wrestlers in WWE history is done.
Taking a look back at his career, I ranked the ten best Undertaker matches from his long, memorable career.
10. The Undertaker vs Bret Hart – SummerSlam 1997
The Undertaker and Bret Hart unfortunately didn’t meet that much during their careers. As the two biggest babyfaces in the company for years, WWE just didn’t book big babyface vs babyface matches often. They did have one really memorable match, anchoring SummerSlam with a grueling contest that showcased the individual brilliance of both men. Shawn Michaels was the special guest referee and his chairshot (intended for Bret) would set up another match on this list.
9. The Undertaker vs Triple H – WrestleMania 28
WWE went all out to try and stack the deck for this match, having The Undertaker wrestle Triple H inside Hell in a Cell at WrestleMania, with Shawn Michaels as the special guest referee. Despite some over the top drama that bordered on campiness, they delivered a truly memorable performance that was billed as being the end of an era. Of course, eight years later The Undertaker would still be in the main event of WrestleMania, but that is another story.
8. The Undertaker vs The Rock vs Kurt Angle – Vengeance 2002
This was a classic triple threat match between three of the biggest stars of the 21st century. A fun match to go back and watch, all three men were arguably at the peak of their careers and delivered a memorable brawl that encompassed all of the good stuff about that era. Big names, wild brawls, exciting spots and thrilling finishes, with The Undertaker juuuusssttt late breaking up the pin, costing him the world title.
7. The Undertaker vs Shawn Michaels – WrestleMania 26
While their encounter the previous year is the more memorable match, there is a real argument that the sequel was better. This was the culmination of a storyline dating back to the first match, with Michaels having been driven crazy by not beating ‘Taker the year before. So Shawn put his career on the line and for the first time it seemed logical that The Undertaker was actually going to have his streak broken. However, ‘Taker “retired” Michaels in one of the best WrestleMania main events in company history.
6. The Undertaker vs Mankind – King of the Ring 1998
This is a strange one to do because it has very little to do with The Undertaker. Perhaps the most memorable match in the last 30 years of pro wrestling, the ungodly bumps and punishment Mick Foley took in this match would and should never be repeated. Could this match have been the exact same if you swapped The Undertaker with Kane? Yeah, probably, but it is still an Undertaker match and no retelling of his career is complete without mentioning it.
5. The Undertaker vs Kurt Angle – No Way Out 2006
This is often forgotten, but as a pure wrestling match it might be the best ‘Taker ever had in his career. No gimmicks, no crazy spots, just pure action and storytelling. The finish, with Angle slipping out of the triangle choke and rolling up The Undertaker to retain the World Heavyweight Championship, is probably the best finish of any Undertaker match. What stands out is that The Undertaker lost this match cleanly, something he rarely did during his career when he was a babyface. It said something about Angle that he was booked to just out-wrestle The Undertaker and beat him cleanly without any interference or controversy.
4. The Undertaker vs Edge – WrestleMania 24
I was torn between this match and their later bout at SummerSlam. While the latter was inside the Hell in a Cell, the former was at WrestleMania and ended up closing the show. I kind of like the WrestleMania match more, it didn’t rely on the Cell, which while entertaining is also kind of gimmicky, and this match involved more traditional wrestling psychology and a fun finish. Edge vs The Undertaker is one of the best feuds in WWE history, and if you haven’t watched any of the matches in a while I highly recommend checking them out on the Network.
3. The Undertaker vs Brock Lesnar – No Mercy 2002
In 2002 Brock Lesnar was getting a monster push and nobody was safe, not even The Undertaker. After dethroning The Rock at SummerSlam to become the youngest WWE Champion in history, Lesnar feuded with The Undertaker. Culminating inside Hell in a Cell, this was one of the bloodiest matches in WWE history with Lesnar, The Undertaker and even Paul Heyman doing blade jobs. If you wanted to sell Hell in a Cell as an epic massacre, this is the kind of match you would use to promote that.
2. The Undertaker vs Shawn Michaels – WrestleMania 25
Sometimes a match gets hyped up so much that it becomes almost impossible for its expectations to be met. This was not one of those matches, because despite sky-high expectations, Michaels and The Undertaker rubber stamped their legacy as two of the greatest performers in WWE history with a sensational back-and-forth match. In some ways the match was almost too good, it raised the standards of future ‘Taker WrestleMania matches to levels that he couldn’t always reach.
Why isn’t this number one? I don’t think it has aged as well as the number one choice. While rewatching the match, it is pretty formulaic, either Michaels or The Undertaker hit a signature move and the other kicks out. While this wasn’t the case at the time, after this match future major matches would follow an endless stream of big move/kick-out sequences. At the time it was mind-blowing, but now it just doesn’t feel as special. Perhaps that is unfair, but I like the number one match a little bit more.
1. The Undertaker vs Shawn Michales – In Your House 18: Badd Blood
What makes this match so good? The Undertaker and Shawn Michaels are still in their physical primes and had a tremendous, athletic contest that just happened to take place inside Hell in a Cell. This was the first Hell in a Cell match, and at the time it was pretty revolutionary. Earlier in the 1990s WCW had tinkered with changes to the traditional steel cage match with concepts like the Chamber of Horrors and Doomsday Cage matches, and they were big duds. The first Hell in a Cell match was a massive success and spawned one of the most anticipated match types in WWE history.
What separates this match from others was the storytelling, with Kane making his anticipated debut and costing The Undertaker the match and the world title. That kind of storytelling has allowed this match to age better than the WrestleMania 25 match, as good as it is. This match has all the action, all the drama, and was the start of something really big with Kane’s debut, and it didn’t rely on the repetitive near-fall sequence like a lot of great matches. Instead it relied on creativity, long-term storytelling, and a multitude of characters, which is why it is number one.