It’s hard to believe that the Undertaker has been around for 25 years. Or, rather, it’s hard to believe that Taker is still wrestling (even at his massively reduced rate) today. The man has seen a multitude of eras come and go, a plethora of stars rise and fall, and still he stands as the pillar of consistency. It’s in that spirit that WWE is celebrating Undertaker Week, in honor of the 25 years since he debuted back in 1990 (funny enough, not as “Undertaker” but as “Cain the Undertaker”), and it’s in that spirit that we take a look back at the best matches from the Phenom.
When re-watching most of these (some have been permanently embedded in memory and/or popular culture), a few trends pop up. First, Taker’s best matches are generally the results of long feuds with one opponent of the kind that don’t seem all that prevalent nowadays. These are half-year feuds with emotional and often brutal payoffs. In that same note comes the second trend: Taker really is the king of Hell in a Cell matches. Five of the top 10 (plus an honorable mention) on this list take place inside the demonic structure that Taker helped usher in all the way back in 1997. The cell plays into the darkest parts of the Undertaker character (easily the best gimmick in the history of professional wrestling), and reminds us that behind the legacy, the nostalgic returns, and the body of work, Undertaker was supposed to be a terrifying personification of evil. Also, he was a biker at some point, but we don’t focus on that too much.
Honorable mention: The death and rebirth of Mankind.
Match: Hell in a Cell
Opponent: Mankind
Date: 6/28/1998
Event: King of the Ring 98
Let's get this out of the way: this match is essentially just two spots. The second Hell in a Cell match ever (spoiler: the first one makes an appearance later on this list) is all about its two ridiculous moments, moments so iconic that they're still being used in memes today. The first, of course, is Undertaker throwing Mankind off the top of the cage onto the announcing table, eliciting the famous "THEY KILLED HIM" Jim Ross sound bite that you hear any time a violent dunk or knockout happens. The second is when Mankind gets choke-slammed through the top of the cage onto the floor. If you are a fan of wrestling, you have seen these spots over and over, and even though Undertaker is the attacker in both, his place in one of the most famous and grotesquely fascinating matches of all time makes this as good a spot as any to start this list.
10. Anything Shawn Michaels can do, Triple H can do worse.
Match: “End of an Era” Hell in a Cell (Special Guest Referee: Shawn Michaels)
Opponent: Triple H
Date: 4/1/2012
Event: WrestleMania 28
Most people would probably have this match closer to the top of this list, and they might not be wrong. The culmination of four years of "big event" Undertaker matches is definitely the best Streak match involving Triple H, but it's impossible to look at both this and the previous year's finisher spamfest without a jaded eye. After all, Haitch's matches came right after Shawn Michaels' two classics (that will be making an appearance later on), and they both paled in comparison. There are two reasons that this match makes the cut instead of the wildly overrated WrestleMania 27 match: 1. the visual of a Hell in a Cell match outdoors in Miami is beautiful, lending that special Florida noir haze to the proceedings, a fitting setting for the "End of an Era," and 2. the inclusion of Shawn Michaels added buckets of melodrama, with the Sweet Chin Music-pedigree near-fall is the closest I've come to believing the Streak would be broken before it was. Not the best match either of these men had, but a worthy start to the top 10.
9. Batista’s WrestleMania 23 beatdown.
Match: Singles match for the World Heavyweight Championship
Opponent: Batista
Date: 4/1/2007
Event: WrestleMania 23
Batista?! Batista. This motherfucker beat the ever-loving shit out of the Undertaker at WrestleMania 23, turning in his best performance in a WWE ring ever. There's no frills or convoluted spots here; this is just two big dudes wailing on each other for an intense 15 minutes. Until Brock Lesnar showed up in 2014 and broke everyone's hearts, this match was the most believable place for the Streak to end from a physical standpoint. After all, Batista was still in his Animal phase, and if anyone could have withstood the nuclear heat that would come from ending the Streak once and for all, it was good ol' Toe Head. Alas, like so many others, he came up short, but the journey to the final Tombstone is a viscerally enjoyable as any Taker match ever.
8. Technical is a four letter word, spelled E-D-G-E.
Match: Singles match for the World Heavyweight Championship
Opponent: Edge
Date: 3/30/2008
Event: WrestleMania 24
From the most physically grueling match of the Streak to the most technical. Having this main event gem the year after the Batista match just goes to show how versatile and simply incredible the Undertaker is. It's an easy story told in the most exciting way: Edge is a piece of shit, and he will go to any lengths to be the man who defeats the Streak. Looking back on it, this is one of the most unlikely places for it to get broken, and there aren't really any near-falls that make you believe otherwise, which hurts it a bit on repeat. But considering how ridiculously overwrought later Undertaker matches would get, there's a joy to be found in how precisely wrestled this match is. The spear-into-Hell's Gate ending is as "Ho-Ly-Shit" as an Undertaker match gets without the presence of Shawn Michaels. This match would be higher if it mattered just a bit more.
7. In a cell with the Beast...again.
Match: Hell in a Cell
Opponent: Brock Lesnar
Date: 10/25/2015
Event: Hell in a Cell 2015
The perfection of the brutal cell match. Nostalgic fans would argue that this was a bit sloppier and not as exciting as their 2002 cell match, but they'd be full of themselves. Maybe due to their development as wrestlers and storytellers over the last 13 years, or maybe because every bump looked like it would kill Taker, this match was as intense as any Undertaker non-WrestleMania match could get. The finale, an F-5 into the ripped ring and exposed planks, is so unique and ridiculous that you couldn't help but gasp. The post-match stuff with Bray Wyatt abducting Taker was awesome, and hopefully will have a great payoff this weekend.
6. The five greatest attitude era wrestlers (and Rikishi).
Match: Hell in a Cell for the WWE Championship
Opponents: Kurt Angle, The Rock, Stone Cold Steve Austin, Triple H (and Rikishi)
Date: 10/10/2000
Event: Armageddon 2000
This match is stupid. There's no other way to put it. Throwing five of the biggest stars of the era (and also Rikishi) into a Hell in a Cell match is, by nature, a very dumb idea. That doesn't mean it isn't a hell of a lot of fun. Taker gets the most famous moment of the match, when he half-choke slams, half-pushes Rikishi off the top into a truck that just happened to be there. Aside from that, the Deadman-Except-He-Was-A-Biker-Here doesn't "do" too much. But just having his presence in the match lends it a bit more credence, given his cell expertise. A quick shout out to the ending, which kept everyone strong by having Kurt Angle steal Stone Cold's pin on the Rock while Austin was fighting off Triple H. Somehow, in a match with five huge egos (and Rikishi), everyone looked like a million bucks (except Rikishi).
5. On the Edge.
Match: Hell in a Cell
Opponent: Edge
Date: 8/17/2008
Event: SummerSlam 2008
This match is Edge at his most vicious, and Undertaker at his most cruel. You would expect this match to play out like a modern version of the Shawn Michaels/Undertaker cell match (coming a bit later), with Taker stalking his undersized prey, but in a brilliant bit of storytelling, it was Edge who dominated most of the match, utilizing every weapon and tactic possible to put down the Deadman. It all came to a climax when the Rated-R Superstar speared Undertaker through the cage wall AND followed it up with another spear through an announcer’s table. Brutal. It was not meant to be Edge’s day, however, as the Undertaker summoned his “I’m dead” cheat code to completely demolish his opponent on the way to finish: a throw through two tables, a spear and conchairto double that mocked Edge as he was hit with his own signature moves, before ending in a Tombstone for the 1-2-3. That by itself would have been enough to place high on this list, but the real ending is legendary: Taker turned around when he saw Edge stir, dragged him up a ladder, and threw him THROUGH the ring as flames erupted all around. A one-way ticket to Hell for Edge, and a one-way ticket to the top 5 for this match.
4. The Sequel.
Match: Streak vs. Career No DQ match
Opponent: Shawn Michaels
Date: 3/28/2010
Event: WrestleMania 26
The sequel. You could make an argument that no two wrestlers had as good of in-ring chemistry as the Undertaker and Shawn Michaels did. They put on two 5-star matches together, 22 years apart, and this final bout is only JUST behind (oops, spoiler). The story was all about heartbreak for the Heartbreak Kid: one mistake cost him a shot at immortality at WrestleMania 25, and he wanted another go at it. The slow unraveling/heel turn by Michaels is perfectly encapsulated in the greatest promo video ever done by the WWE, and by the time WrestleMania 26 rolled around, the match had escalated to a Streak vs. Career match: the greatest record in sports entertainment vs. one of the greatest bodies of work in history. The match itself played on a lot of the same beats as the previous year's masterpiece, with the added drama that no one in the history of wrestling did melodrama as well as Michaels. It was sloppier than it probably should have been, but that really only added to the urgency felt by both men, and of all the matches on this list, none top this one's finish. A beaten-down Michaels kicks out of a second Tombstone, and Undertaker yells for him to stay down. But HBK ain't no punk, and he grabs onto the Undertaker, standing up and delivering one last slap and taunt before being put away with a JUMPING GODDAMN TOMBSTONE. R.I.P., HBK.
3. CM Punk’s last hurrah.
Match: Singles match
Opponent: CM Punk
Date: 4/7/2013
Event: WrestleMania 29
The only man to put on an Undertaker match rivaling Shawn Michaels' work is another undersize, cocky technician. CM Punk's best heel work to date (sorry, Straight Edge Society) took this feud into a deeply personal level, as the Best in the World mocked Taker for the (real-life) death of his mentor, Paul Bearer. There wasn't too much drama here because of that; no way was Taker losing after Bearer passed away. That didn't stop these two from putting on a character clinic, with Punk trying everything he could to rattle the Deadman, and coming damn close. The patented Undertaker sit-up during the Anaconda Vise is one of the coolest late-period Taker moments, and Punk selling the horror told stories lesser wrestlers could only dream of. The reason this match isn't higher, to be honest, is that the finish dragged on a bit longer than it needed to, but that's a small quibble for CM Punk's last WrestleMania match and Taker's last classic at the Showcase of the Immortals (for now, anyway).
2. The Cell that started it all.
Match: Hell in a Cell to determine the No. 1 contender for the WWF Championship
Opponent: Shawn Michaels
Date: 10/5/1997
Event: Badd Blood: In Your House
Objectively speaking, this is the greatest Hell in a Cell match of all time, and it just so happened to be the first. Unlike the shoehorned cell matches of today, the creation of the cell was demanded by the feud between Michaels and Undertaker; the former was the European Champion at the time, and was getting by his defenses with help from cronies Triple H and Chyna. He had cost Taker the WWF Championship at SummerSlam 97, and so set the stage for a match with a shot at the big belt on the line, with no interference (well, or so we thought). While not as batshit insane as the Mankind spot from the following year, the most iconic moment of the initial HIAC match comes with Shawn Michaels barely hanging on to the cage before being tossed overboard onto the announcer's tables. And, well, if you don’t remember that, you probably remember the debut of Kane, Undertaker’s demon brother from hell, who would rip the door off the cage and attack a beaten-down Taker to give Michaels the win. From a memorable spot, to intricate and violent offense inside the cage, to a surprise that would change the face of WWE for decades to come: this match had it all, and then some. Hell in a Cell matches are still, to this day, trying to top this majestic ode to violence.
1. The Undertaker's masterpiece.
