The Last Outlaw: The Greatest Matches of The Undertaker

The Undertaker Greatest Matches

The Undertaker is a wrestler that defies explanation. No succinct manner of description will do the job justice. His entrance is cinematic, his in-ring body of work unparalleled, and his storytelling ability unmatched. Narrowing down a list of The Phenom’s greatest matches down, even to the eleven presented here, was hell. Further troubles came from separating the matches from the epic moments, which will be counted down another time. But from The Deadman to the Phenom, The American Badass to The Last Outlaw, and every damn thing in between, these may be the greatest in-ring performances of The Undertaker. Some are to be expected, while others deserve a second look, especially with the benefit of hindsight.

Rated-R Main Event - vs. Edge at WrestleMania XXIV

In his record twenty-seven appearances at WrestleMania, Undertaker was in the main event of the spring spectacular three times, four if you count night one of this year’s ‘Mania. His adversary for this show was “The Ultimate Opportunist” Edge, who won the World Heavyweight Championship at December’s Armageddon show, in a Triple Threat involving both Undertaker and defending champion Batista. The setup was completed when Undertaker won the Elimination Chamber match in February 2008, earning number one contender status.

This was the first time The Undertaker won a match in “The Streak” by submission, as this was around the time he debuted his gogoplata hold, dubbed “Hell’s Gate.” For the first time since Undertaker’s streak was considered honest stakes for a match, it felt in real danger, as Edge pulled out every trick in his extensive book to defend his gold, only to submit and hand The Phenom his second reign with the Big Gold Belt, and his sixth world championship in WWE.

Heaven and Hell - vs. Shawn Michaels at The 25th Anniversary of WrestleMania

Not only did Undertaker outdo himself the following year, but he and Shawn Michaels tore the house down in what many consider the best ‘Mania match this side of Steamboat vs. Savage. The premise for this showdown was simple: The Heartbreak Kid had done basically everything he wanted to in WWE, and his “Mr. WrestleMania” moniker needed just a bit more legitimacy.

The entrances alone were worth the price of admission, as Michaels, dressed all in white, descended from the heavens to lay the demon to rest. Undertaker rose from a platform, while flames poured out around the stage. It goes on and on and on, as the late Ronnie James Dio, would sing, and this match was Heaven and Hell. Even a slightly botched tope suicida that took out a cameraman and saw The Deadman land headfirst couldn’t take away from this half-hour clinic, and even the heightened “Streak vs. Career” stakes the following year couldn’t help the sequel excel over the original.

Blood and Steel - vs. Brock Lesnar at No Mercy 2002

Hell in a Cell is a stipulation forever associated with The Undertaker, having made fourteen total appearances in the satanic structure. In just the ninth overall Hell in a Cell match, which itself was The Deadman’s sixth, Undertaker, firmly in his American Badass persona, challenged “The Next Big Thing” Brock Lesnar for the WWE Championship, after Taker got himself disqualified in their first encounter the previous month at Unforgiven.

To call this match gruesome is to do it a disservice. Not only did Lesnar and Undertaker bleed significantly, but so did Lesnar’s manager/advocate Paul Heyman, after Taker reached through the links in the cell wall and grabbed The Mad Genius by the tie, before slamming his face into the cold steel several times. As far as WWE is concerned, the Muta Scale was off the charts for this one, with the challenger Taker’s face resembling the lauded “crimson mask” before the final bell. Lesnar’s eventual victory cemented him as a legitimate top guy, a highly credible champion, and would lead to so many more classic moments between the two for years to come.

Broken in Half - vs. Mankind at King of the Ring 1998

Let’s be serious for a moment. If you’ve only ever seen one visual of professional wrestling, I’m willing to wager that Mankind’s fall off the top of the cell is it. If you’ve only ever heard one call from professional wrestling, I’m also willing to wager that it’s Jim Ross screaming “As God as my witness, he is broken in half!” This showdown wasn’t even a tournament match, nor was it for a championship or contendership. Mankind had faced Kane inside the structure just two weeks prior on RAW, leading to this legendary match-up.

Even twenty-two years later, it’s difficult to watch at times, especially knowing what we know about the condition of both men. Undertaker went into the match with a legitimate foot injury, and the initial fall separated Mankind’s shoulder. The second major bump, a Chokeslam through the cell roof, knocked Mankind unconscious, to the point where agent and Foley’s friend Terry Funk bought time for the Hardcore Legend by a) per Undertaker’s request, checking Foley’s pulse to make sure the man is still alive, and b) having Undertaker Chokeslam the deathmatch icon out of his shoes.

And then there’s the thumbtacks. If you haven’t watched the match, seek it out.

Ratings Gold with the Rattlesnake - vs. Steve Austin on the June 28, 1999 RAW IS WAR

One year after that fateful encounter with Mankind, Undertaker defended the WWF Championship against “Stone Cold” Steve Austin in a match that made history. For one, the show that night was in Charlotte, NC, long considered the backyard of rival Jim Crockett Promotions, later and perhaps more famously known as World Championship Wrestling. Even though the Monday Night War was completely non-competitive by this point, the championship match pulled a staggering 9.5 rating, translating to over 10.7 million viewers. After a pair of Stone Cold Stunners, Austin won the match and redeemed himself after his loss at Over the Edge, notching his fourth of six WWF/E Championships. Even in defeat, Undertaker shared this historic moment with The Rattlesnake, and the title change set up a chaotic First Blood match for Fully Loaded the next month.

Blackjack - vs. CM Punk at Wrestlemania XXIX

As what would be the final victory in “The Streak,” this match managed to strike the balance of reality and storyline, and having two of the best workers at the time hurt precisely nothing. In the lead-up to the showdown, Undertaker’s longtime manager Paul Bearer sadly passed away, and the use of Bearer’s death in storyline was uncomfortable, though the argument could be made that the man once known as Percival Pringle III would have wanted it that way, if he had any say.

Coming off of the longest WWE Championship run of the Modern Era, CM Punk felt like he could seriously end The Streak. The match was a great showing, and one of the last times that Undertaker looked and felt like he could hang. The two worked their asses off, not to mention the “Voice of the Voice of the Voiceless” Paul Heyman at ringside selling the whole affair from ringside like his life depended on it. It might be second-only to Money in the Bank 2011 in Punk’s body of WWE work, but for Undertaker’s post-hip surgery run, it might be his finest hour.

Match Within a Match - vs. Shawn Michaels in the 2007 Royal Rumble Match

Before we got a pair of bonafide classics from the two, the Heartbreak Kid and The Deadman ended up as the final two of the 2007 Royal Rumble Match. The “match within a match” trope in multi-man melees hasn’t been done better since this epic encounter. Undertaker entered the Rumble at the coveted number 30 spot, so he was the freshest man in the match. Shawn Michaels had just ended his D-Generation X reunion with the now-injured Triple H, so a title match at WrestleMania would be a great comeback.

In the end, The Undertaker would become the first man to win the Rumble from the final entry slot, going on to win the World Heavyweight title from Batista at The Show of Shows. Not to be outdone, Shawn Michaels would win the number one contendership to the WWE Championship, challenging John Cena in the main event of WrestleMania 23. Was this standoff the level of either of their ‘Mania matches? Frankly, not even close, but it was a sign of things to come for the two legends.

Respect - vs. Jeff Hardy on the July 1, 2002 RAW

While he donned the American Badass persona, one of Undertaker’s signature lines went “try me, and I’ll make you famous.” Jeff Hardy was best known for his work in tag team action with older brother Matt, with his Intercontinental Title victory the year prior being sold as a fluke. After losing the week prior on RAW, Jeff challenged the American Badass to a Ladder Match for Taker’s WWE Undisputed Championship, seemingly putting the title reign in jeopardy given the Hardy’s penchant for such a match.

This match was responsible for one of the greatest calls by Jim Ross: “Climb the ladder, kid! Make yourself famous!” And Hardy damn sure did, even though he didn’t walk away with the championship that night. Even preoccupied by his future title defenses against Kurt Angle and The Rock, not to mention being out of his element in a Ladder Match, Undertaker retrieved his title following an elevated Chokeslam, and even raised Hardy’s hand after the Rainbow-Haired Warrior refused to stay down. The match is celebrated as one of the greatest televised main events in company history, and with good reason.

Triple Threat For The Title - vs. The Rock vs. Kurt Angle at Vengeance 2002

Speaking of The Rock and Kurt Angle, this match may be the greatest Triple Threat Match that WWE have ever put on. Undertaker had The Rock in his sights already, stemming from The Great One’s interference at King of the Ring. On the July 4th edition of SmackDown, a controversial ending to the Undisputed Title match between champion Undertaker and challenger Angle led to The Olympic Hero’s insertion into the pay-per-view main event.

Even if Undertaker wasn’t involved in the fall that would give The Rock a then-record seventh WWE Championship, it capped off what was an eventful month for Undertaker as champion. He may be a character that doesn’t need a championship, but if Undertaker is holding one, that hardware can only be elevated as a result.

Defining a New Era - vs. Edge at SummerSlam 2008

This Hell in a Cell match was special for its parameters, as it was the first pay-per-view main event to happen during what many fans call the “PG era.” For those not in the know, the company was working out major sponsorship deals with corporations such as Mattel. In addition, after a blood feud between Shawn Michaels and Chris Jericho went truly bloody at the previous month’s Great American Bash, the time-honored practice of “blading” (nicking one’s forehead with a small razor to draw blood, adding drama to a match) was outlawed in WWE.

As such, the traditionally violent Hell in a Cell match seemed to suffer as a result, at least on paper. Ten years after the most infamous iteration, it looked as if this installment would be neutered in the name of big sponsorship money. Leave it to two ring generals like Edge and The Undertaker to construct a fittingly chaotic match, with tables, a busted cell wall, steel chairs, and a wild post-match segment that saw The Phenom Chokeslam the Rated-R Superstar straight to hell.

The stipulation would jump the shark the following year, after a pay-per-view event was dedicated to the match type not just for a one-off, but annually since 2009, but at least here, there was hope for the feud-ender in the new, sanitized PG Era.

Legend vs. Legend Killer: The Finale - vs. Randy Orton at Armageddon 2005

I’m not saying that there isn’t a great Hell in a Cell match that didn’t involve The Undertaker, but more often than not, the match type benefits from his presence. The star-making feud between Undertaker and Randy Orton had a strong beginning at WrestleMania 21, a great middle section at SummerSlam and No Mercy, and culminated in a Hell in a Cell match at Armageddon.

Whatever critics Randy Orton had remaining after his infamous Hardcore Match with Cactus Jack at Backlash 2004 were likely silenced here, as the Legend Killer proved he could hang with the very best. Closing out the event was a bloody affair where everyone, including Randy’s dad and second “Cowboy” Bob Orton and even referee Mick Patrick was lacerated in the ensuing half-hour in Hell. Old-school wrestling dictates that a feud end in a tense stipulation match, and this contest upheld that tradition better than most.