The 8 Greatest Ups And 7 Worst Downs Of The Undertaker’s Career

When we talk about the greatest professional wrestlers to ever live the conversation usually ends up as a discussion about household names like Hulk Hogan, “Stone Cold” Steve Austin, John Cena and Dwayne “The Rock” Johnson. But the reality of that topic is far more complex because once you’re actually on the inside of wrestling fandom you realize the most famous wrestlers aren’t always the best wrestlers. In fact, many of wrestling’s most revered legends aren’t names that would be instantly recognizable to someone who has never watched wrestling.

If the conversation is about those who have made an impact by being the muscle of the wrestling industry, we get into the more internally respected performers like “The Nature Boy” Ric Flair, Shawn Michaels and Bret “The Hitman” Hart. However, even those men can’t claim the level of reverence earned by the man they call “The Phenom,” the Undertaker.

As the Undertaker, Mark Calaway has built a legacy unlike that of any wrestler in history. For nearly thirty years, the Undertaker has loomed above main event status like a dark cloud over any and all challengers, an unprecedented and uninterrupted reign at the top of the mountain. The Undertaker’s situation is unique in that he never needed championships to validate his position as the most feared WWE Superstar on the roster, but even the Dead Man isn’t immune to missteps, and a career this long will inevitably be peppered with them. Here are the greatest ups and worst downs of the Undertaker’s career.


15 Up: 1990 Debut

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In the height of a time full of cartoon wrestling gimmicks like barbers and Elvis impersonators, it’s easy to see why some level of pessimism surrounded the Undertaker’s debut at Survivor Series 1990. He was introduced as sort of a zombie mortician, his skin painted pale underneath a black Stetson hat and trench coat. To camp it up just a little bit, he was accompanied by a similarly-dressed man with an urn named Paul Bearer. It was doomed to be just another goofy shtick lost in the shuffle, except it wasn’t.

The Undertaker character, and the Paul Bearer character for that matter, persevered. Undertaker would evolve with every shift in the demands of the wrestling audience and continue to be one of WWE’s top draws, which is why his debut as a silly undead wizard in 1990 stands the test of time as such an iconic moment for pro wrestling.

14 Down: Killing Paul Bearer

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In 2004 WWE decided to revive an old WCW favorite with the Great American Bash pay-per-view. The event is steeped in rich wrestling history but when WWE resurrected it they’d taint it with one of the wackiest storylines in wrestling. The Undertaker was set to face the Dudley Boyz in a two on one handicap match and SmackDown General Manager Paul Heyman had threatened to encase Paul Bearer, the Undertaker’s manager and on-screen father, in concrete on the stage if the Undertaker didn’t voluntarily lose the match.

The Undertaker didn’t crack under the pressure and actually managed to defeat the Dudley Boyz, but after the match the Undertaker apparently decided having his father around was a weakness and took it upon himself to drown Bearer in concrete anyway. You think he could have instead just sent him home or something, but that's not nearly as dramatic. So there it was, patricide on live pay-per-view, except somehow Bearer survived and appeared on WWE television years later.

13 Up: Ladder Match with Jeff Hardy


One night in 2002 WWE would shock fans with an unexpected classic for the ages when Jeff Hardy was booked to challenge for the WWE Championship against the greatest legend in the sport, the Undertaker. It’s worth noting that, at this time, Jeff Hardy was at a certain peak in popularity. Jeff has always been a fan favorite, but he was really on fire in 2002. Although Jeff wasn’t main event status, he was getting just the right crowd reactions and getting enough screen time that it was almost believable that WWE could pull the trigger on making him a megastar on this night.

The match was absolutely thrilling. Everything, from the mechanics to the crowd investment and the commentary of WWE Hall of Famer Jim Ross was on point. In what once listed it as one of Raw’s greatest matches of all time, Jeff Hardy came within a hair’s thickness of the biggest upset in all of wrestling but the Undertaker ultimately prevailed. It was a gem of a contest and the Undertaker’s illustrious career was better for it.

12 Down: American Badass


At WWE’s Judgment Day pay-per-view in 2000, The Rock and Triple H battled for an hour in an Iron Man match for the WWE Championship and what resulted was a showdown for the ages between two bitter rivals, but the real story coming out of that event was the Undertaker returning from a months-long hiatus and causing total havoc in the closing moments of that main event. The Undertaker was riding a motorcycle and wore a bandana and sunglasses, all very uncharacteristic of the gothic character we’d come to know and love.

If you only look at that moment in and of itself, it was pretty exciting. But that return signified years of the “American Badass” version of the Undertaker. While that Undertaker had plenty of amazing matches and moments, he never truly felt like the Undertaker and fans were clamoring for their Dead Man to once again rise to the surface. When he finally did years later, it felt as if the Undertaker hadn’t even been around. The Undertaker going back to his creepy ways felt like coming up for air for many wrestling fans.

Because the American Badass humanized an otherwise mysterious legend, his debut stands as one of the lows in Mark Calaway’s career.

11 Up: First WWE Championship Win


In 1990 the Undertaker made his debut and the WWE Universe was mystified. One year later at Survivor Series he was just as scary and dominant as he’d been since the beginning, and he was already at the top of the mountain, challenging the most famous wrestler of his era for the WWE Championship. The stage was set for the Undertaker to face “The Immortal” Hulk Hogan, the same Hogan who had essentially held the WWE Championship nonstop for the previous decade and had been in just about every WrestleMania main event to that point. Hogan had legions of die-hard fans, and even though the Undertaker seemed unbeatable, they never thought that their hero wouldn’t be able to find a way to put him down.

As fate would have it, the Undertaker was not destined to be one of those stars who WWE brought in and built up just to fall at the feet of Hulk Hogan and make the American hero look even stronger than before. In fact, it was just the opposite, as the Undertaker soundly defeated Hogan and won his first WWE Championship, kick-starting a career full of momentum which would never be slowed.

10 Down: Muhammad Hassan Controversy


It seems that no pro wrestler is immune to controversy. Every athlete who steps into the ring seems to be tied to at least one scandal over the course of his or her career and even a legend as deeply revered as the Undertaker stands as no exception to the rule. In 2005 he was embroiled in a rivalry with Muhammad Hassan, an Arab-American Superstar who repetitively criticized the United States along with his manager, Daivari.

Weeks before Hassan was to meet the Undertaker at the Great American Bash in 2005, Hassan and several masked men brutally assaulted the Undertaker with several weapons, one being a piano wire they used to choke out the Phenom. This aired on television around the same time as the London bombings and comparisons were inevitably drawn between the storyline and terrorism. WWE was forced to drop the Muhammad Hassan character following the match at the Great American Bash and all the drama makes this one of the low points in the Undertaker’s career.

9 Up: WrestleMania XXIV versus Edge


In 2008 longtime WWE Superstar Edge had finally established his spot in the main event, reigning as the World Heavyweight Champion and going into WrestleMania XXIV defending the title against the Undertaker. It was a sort of point of arrival for Edge, especially considering the match was going on in the coveted closing spot on the show. Edge had proven to be a reliable top Superstar, but he’d never been tested in such a high-pressure scenario.

Ultimately, Edge lost the title that night to the Undertaker, but he proved he was exactly where he belonged as both men put on one of the best matches of their respective careers. It was an emotional masterpiece and one of WrestleMania’s greatest Championship matches. The Undertaker and Edge had amazing chemistry and following this classic encounter they would go on to lock up again months later inside Hell in a Cell at SummerSlam.


8 Down: The End of the Streak

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Since 1991 WWE and the Undertaker have created an idea that has become as legendary as the Dead Man himself, an idea known as “the streak.” The streak is the most respected and amazing thing ever to have existed between the ropes of a wrestling ring. In 1991 the Undertaker won his first match at WWE’s grand annual spectacle, WrestleMania. He also won the next one, and the one after that, until eventually the WWE Universe was seeing something magical take shape before their very eyes in the form of the most impressive winning streak ever seen.

Fast forward to 2014 and the Undertaker has twenty-one consecutive WrestleMania victories behind him and he’s going in for the twenty-second, but this time his opponent, Brock Lesnar, actually does the unthinkable and defeats him. The audience was completely speechless; silence filled the arena and even Lesnar’s manager, Paul Heyman, was freaking out at the death of the streak. It was actually a very, very cool moment, and proponents argued that it was the right decision for everyone involved but perception is reality and the fans perceived this to be the end of the Undertaker’s great WrestleMania performances.

7 Up: Hell in a Cell versus Mankind


The Undertaker has made a career out of making other wrestlers famous. Sometimes that comes in the form of a rare victory over the Undertaker; other times just a really hard-fought match. In 1998 the Dead Man was about to take a man who already had a respectable career and decent following in Mick Foley and gave him the moment that would come to define his entire legacy.

No one knew what they were in for that night at the King of the Ring pay per view, including the wrestlers themselves. The plan was for the Undertaker to toss Mankind off the top of the cell down to the floor, which happened, but later when Mankind crawled back to the top, he accidentally went through the top of the cell and landed in the ring. It was an unexpectedly brutal war which became a highlight for both the Undertaker and Mankind.

6 Down: Hanging the Big Boss Man


The Undertaker’s WrestleMania story is the stuff of legend. WWE often likes to call Shawn Michaels the greatest WrestleMania performer of all time, but the Undertaker is the only man who can probably make that claim and have sturdier legs to stand on. One of the notches on the belt that his the Dead Man’s WrestleMania streak came in 1999 when he battled the Big Boss Man inside Hell in a Cell. Unfortunately, it was one of his least memorable bouts.

The match itself was underwhelming, especially when you consider that WWE’s most respected Superstar of all time was carrying the workload. Granted, the Boss Man was never known for his technical wrestling prowess, but the match quality is an afterthought compared to what came next. Once the Undertaker had defeated his opponent, he hung the Big Boss Man on a rope right in the middle of the ring. It was one of many awkward cases of outright murder by the Undertaker.

5 Up: WrestleMania 23 versus Batista


Batista was already a big star in 2007 when he was preparing to face the Undertaker at WrestleMania 23. The man known as “The Animal” had spent a lengthy amount of time in the group Evolution, and then feuded with the faction’s leader, Triple H. Batista was going into his match with Undertaker as the World Heavyweight Champion, but despite the fact that the Undertaker would ultimately defeat him, Batista’s career would get a major boost.

The Undertaker gave Batista what many members of the WWE Universe say was the best match of Batista’s career, and it was even one of the Undertaker’s best showings. It was brutal, and more importantly, it was believable that Batista could actually be the one to finally end the streak. That wouldn’t be the case, of course, but it was an awesome enough fight that Batista could have retired immediately after with a Hall of Fame-worthy career.

4 Down: Imposter Undertaker


Wrestling is full of goofy storylines, especially when you look at basically any period of time before the Attitude era. That’s not to say anything post-1998 is gold, there was the storyline where Kane started seeing visions of his former self, visions the fans could also see, and he ended up battling an imposter version of Kane. That epic fail of a storyline was eerily similar to one that came earlier in 1994 involving our beloved Undertaker.

The Undertaker was missing in action for a while when “The Million Dollar Man” Ted DiBiase claimed to have found him. He proceeded to bring in an imposter Undertaker, played by professional wrestler Brian Lee, although literally no one was fooled by the look alike. Just as many people found this storyline entertaining, even after the Undertaker returned to face his imposter in a match at SummerSlam that year. Indeed, there have been a lot of imposters in wrestling storylines throughout the years, but this one was particularly a snooze fest.

3 Up: WrestleMania XIV versus Kane


Pro wrestling isn’t exactly known for its award-winning narratives. In fact, the argument could be made that the industry exhibits the most fragmented and inconsistent stories in the entire entertainment industry. Storylines are frequently dropped cold turkey because the audience isn’t taking to them and lifelong rivals sometimes find themselves teaming together without so much as a mention of their rocky past. However, one storyline in the late 1990s changed the stereotype.

The Undertaker’s brother, Kane, made his long-teased debut by attacking the Dead Man. As the story goes, Kane was burned in a fire set by the Undertaker when they were younger, and now a scarred Kane was out for revenge. Initially, the Undertaker refused to fight his brother, but over the course of several months, the well-played rivalry grew in intensity until they met at WrestleMania XIV in an emotional, classic encounter. It was one of the finest pieces of storytelling in any industry, not just wrestling, and is held up as an example of what a wrestling storyline should aspire to be.

2 Down: WrestleMania IX versus Giant Gonzalez


The Undertaker has been a dominant force in WWE for almost thirty years. A man of his size, athleticism, and presence who has been on top of the main event scene so consistently is bound to encounter some roadblocks in the form of monstrous opponents. Some of those opponents in the Undertaker’s case have been the Big Show, the Great Khali, and his own on-screen brother Kane. The Phenom has managed to make most of the big men he’s competed against look pretty intimidating, but his match at WrestleMania IX against Giant Gonzalez was just a tragedy to behold.

The match was sloppy because Gonzalez really couldn’t do all that much with his gargantuan stature, but that wasn’t even the worst of it. WrestleMania is supposed to be the biggest night of the year where storylines culminate in a satisfactory climax, but WWE attempted to keep both men’s records intact by having the Undertaker win by disqualification when Gonzalez smothered him with some sort of mystery substance. It was wacky, but more importantly, it was a cheap finish to what was probably the Undertaker’s worst outing at WrestleMania.

1 Up: WrestleMania XXV versus Shawn Michaels


The illustrious and decorated careers of the Undertaker and Shawn Michaels have been intertwined for a long time. They battled all through the Attitude era and in fact it was a match against the Undertaker which took four years off Michaels’ career. It was time to settle the score in a WrestleMania dream match at WrestleMania XXV.

Everyone knew this would blow the roof off the building because these men are two of the best wrestling performers of all time. However, the WWE Universe did not count on witnessing what has now been called the greatest match in the history of WrestleMania. Both of them much closer to the end of their careers than the beginning, they managed to turn back the hands of time and construct a masterpiece. Their chemistry was so mind-blowing that they did it again one year later at WrestleMania XXVI and put on a show that almost lived up to the original, something almost unheard of for a wrestling rematch.

It may have been the best match either of these icons ever wrestled, and it was at this late stage in the Undertaker’s wrestling career that he managed to create his finest work.


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