The opinions expressed in this article are those of the author and do not reflect the views of WrestlingInc or its staff
#10 The Undertaker
A towering figure from east Texas, The Undertaker has been undisputedly the best pure gimmick wrestler in the history of the industry. Not only was he able to execute a really good act to perfection, but his combination of athleticism, timing and consistency in the ring have cemented his reputation as one of the best in-ring performers as well. When you factor in the mesmerizing longevity of his career, a case can be made that The Undertaker is the greatest wrestler in WWE history.
Although it is hard to imagine, The Undertaker was not born wearing all black and his eyes were not rolled back into his head. Mark Calaway was born in Houston and grew up in the city. A tremendous athlete in high school, he played basketball at Angelina College and Texas Wesleyan University and considered pursuing a career in Europe before focusing on professional wrestling. He was trained by masked big-man Don Jardine and broke in with World Class Championship Wrestling.
For whatever reason, something about Calaway must have screamed gimmick, because he was given a lot of them early in his career. His original ring name was Texas Red, mainly because he was from Texas and he had red hair, and his first match was against the legendary Bruiser Brody in 1984. He spent four years toiling on the undercard of WCCW, which is hard to believe considering his size and his obvious natural talent. Later he moved onto the United States Wrestling Association in 1988. His gimmick in Memphis was that of The Master of Pain, an ex-con who had spent years in prison for murdering a couple of men in a fight. He was given a monster push, defeating Jerry Lawler for the USWA Unified World Heavyweight Championship just a few weeks after his debut, although he would drop the title back to Lawler shortly after.
He made it to World Championship Wrestling in 1989 and was given the ring name, Mean Mark Callous, a character closer to The Undertaker. Callous was presented as a gothic figure, wearing all black and Jim Ross announced that he had a fondness for snakes and the music of Ozzy Osbourne. He teamed up with Dan Spivey as a part of The Skyscrapers and was given a decent push. As a pair of big men, it was believable that they could physically brawl with The Road Warriors, who were arguably the most popular act in the company. However, Calaway caught a bad break when Spivey left the company right before a big Chicago Street Fight against The Road Warriors at WrestleWar 1990 and Calaway left the tag team. Still using the Mean Mark Callous name, he teamed up with Paul E. Dangerously and he did earn a United States Heavyweight Championship match against Lex Luger at The Great American Bash 1990, losing to Luger and then departing the company shortly thereafter.
He then came to the World Wrestling Federation and was given the name Kane the Undertaker. He made his debut on a TV taping of WWF Superstars, and would make his official debut at the 1990 Survivor Series as the mystery partner of Ted DiBiase’s tag team. After eliminating Koko B. Ware, he ended up getting counted out while he brawled on the outside, ignoring the referee’s count.
The Undertaker’s gimmick is arguably the most brilliant idea Vince McMahon has ever had when it comes to an individual’s character. Today, the idea of someone coming into the company with a gimmick as in-depth as The Undertaker seems archaic, guys have gimmicks, but they are mainly just archetypes. The Undertaker didn’t even have a real name, he was simply The Undertaker. The Undertaker came along when gimmicks were everywhere in the company, and almost all of them were horrible. The Undertaker could have easily gone the way of The Red Rooster, Adam Bomb, The Goon, Man Mountain Rock, The GobblyGooker, Max Moon, Bastion Booger, The Manotaur, Tugboat and many others, if not for the brilliance of the gimmick and Calaway’s ability to portray the character.
The Undertaker is based on the western mortician of the same name, a very outdated occupation that magnificently turned into a great gimmick. A couple things working in his favor were that he was given a great costume, complete with an old-timey western hat and gloves, and he had what a lot of people feel is the greatest entrance of all-time. The brilliant funeral march conducted by WWE music man Jim Johnston, later complete with superb lighting and other effects, would get him over with any fan, even if they had never heard of him before the lights went out. He also utilized the Tombstone Piledriver as his finisher, probably the most brilliantly named finishing move in history. After debuting with Brother Love as his manager, he was given Paul Bearer, a ghostly figure who used to run a funeral parlor, who carried a mystical urn that reportedly powered The Undertaker. All of those things combined with his athleticism turned him into a terrific character that immediately got over with fans.
The Undertaker was originally given probably the most ridiculously overpowered push in wrestling history when he first began. Not only did he win every match in mere minutes, he was presented as a magical character, impervious to pain and regularly no-sold high impact moves. After defeating his opponents, he would morbidly put them in a body bag and carry them out of the arena, in theory to “dispose” of them. The mega-push worked extremely well, as The Undertaker rapidly became one of the most popular wrestlers in the company, and he would go on to squash Jimmy Snuka at WrestleMania VII and feuded with The Ultimate Warrior.
At Survivor Series 1991, just a year after his debut in the company, he would defeat Hulk Hogan for the WWF World Heavyweight Championship after Ric Flair interfered, making The Undertaker the youngest WWF world champion in history up until that point. Despite the fact that he was meant to be a heel, The Undertaker received a rousing ovation from the crowd for defeating Hogan, paving the way for a babyface turn later. He would lose the title to Hogan just six days later at an impromptu PPV titled “This Tuesday in Texas” when a plan to use the urn against Hogan backfired.
He formed a brief alliance with Jake Roberts, but turned babyface when he stopped Roberts from assaulting Randy Savage and Miss Elizabeth with a steel chair. He would defeat Roberts at WrestleMania VIII. He would then begin an often-forgotten about time in his career. With the WWF beginning to build around younger stars, The Undertaker became a pillar of the company. His mystique was already so much that he really did not need a championship to draw, in fact it wouldn’t be until 1997 when he would regain the world title, despite being arguably the most popular wrestler in the company during that time period. While the WWF began to push other stars as title contenders, like Bret Hart, Diesel, Yokozuna and Lex Luger, The Undertaker remained stuck on the outside looking in. The irony was that because The Undertaker was so over, he didn’t get the marquee spot on the card, instead it went to guys who really needed it.
The result of this booking was a long rivalry with Harvey Wippleman. Wippleman would recruit various monsters to take down The Undertaker, similar to the way Bobby Heenan tried to take down Hogan in the 1980s. It made sense for The Undertaker to face enormous challengers, like Kamala, Giant Gonzalez and Yokozuna because his mystique was so great that it was unrealistic that normal sized wrestler could beat him. However, most of the wrestlers he faced, were not very good in the ring, with Gonzalez being the worst, and The Undertaker was struggling to carry overmatched opponents to even passable matches. He beat Gonzalez at WrestleMania IX when Gonzalez was disqualified for choking The Undertaker out with a chloroform rag, eventually winning cleanly at SummerSlam. He would get a title shot against then-world champion Yokozuna, but was unable to win the title, ending in a 1994 Royal Rumble match that saw The Undertaker lose in a casket match when nearly 20 villains came out to beat him. He would then be taken off TV to heal from a back injury
A storyline would develop in his absence. Since the last time anyone had seen The Undertaker was in a casket, it was presumed in storyline that he was dead. Of course this would be the first of many times when it was revealed that The Undertaker could not be killed; although more attempts have been made on his life than pretty much every other wrestler in history combined. Ted DiBiase and his Million Dollar Corporation re-introduced The Undertaker to live audiences in April of 1994, but it turned out to be a fake Undertaker, played by journeyman wrestler Brian Lee. The REAL Undertaker would return and confront his doppelganger, defeating him at SummerSlam. He would however suffer an injury to his orbital bone, forcing him to miss additional time.
Up until this point The Undertaker was known for being a terrific character and a big draw for a struggling company. However, perhaps the most memorable thing about his incredibly memorable career was how good of a worker he was. In the discussion for best big man worker of all-time, it’s really a debate between The Undertaker and Jumbo Tsuruta; he was that good. However, that was not always the case; during the first five years of his time in the WWF he was forced to often work with larger, less-coordinated wrestlers and the idea of The Undertaker having consistently good matches was a foreign concept to fans. It was not until the latter half of the decade when he began to work with highly skilled smaller wrestlers did he become regarded as being one of the best wrestlers in the world.
He challenged Bret Hart for the WWF World Heavyweight Championship at the 1996 Royal Rumble, but lost when Diesel interfered. The Undertaker would return the favor, costing Diesel the title in a cage match with Hart, when The Undertaker emerged from underneath the ring and dragged Diesel through the broken canvas. The Undertaker would defeat Diesel at WrestleMania XII in the finale of their feud. He would then be introduced to one of his greatest rivals, Mankind, a new character in the WWF designed specifically to feud with The Undertaker. Escorted to the ring by Paul Bearer, the sadistic Mankind was one of the few wrestlers to secure consistent victories over The Undertaker. Mankind got the better of The Undertaker in two unique matches, the first a Boiler Room Brawl at SummerSlam and then a Buried Alive match at the event of the same name.
He recovered from being buried alive to return at Survivor Series, defeating Mankind in a match where Bearer was hung in a cage above the ring. He also debuted a new, modified look that saw him drop many of the mortician mannerisms and instead portraying a gothic, more natural character. Calling himself “The Lord of Darkness” the new Undertaker was able to connect with fans a bit more, his promos were no longer limited to short statements and it gave him a little more function in storylines. He started to feud with Vader, with Bearer aligning himself with Vader and costing The Undertaker a match at the 1997 Royal Rumble. He would however, capture his second world championship, defeating Sycho Sid in the main event of WrestleMania 13.
The Undertaker would hold onto the championship until SummerSlam, when Shawn Michaels inadvertently cost him the title in a match against Hart. They fought to a double-count-out at Ground Zero and set up the very first Hell in a Cell match, an expansive cage match that would become known for being the trademark of The Undertaker. At the same time, Bearer had been releasing promos about The Undertaker’s mysterious past. According to Bearer, The Undertaker’s parents ran a funeral home (which Bearer worked at) but they died when The Undertaker burned the business to the crowd, killing his parents and presumably his younger brother Kane. The Undertaker denied the claim and said that Kane had been the one to start the fire. Bearer then revealed that Kane was in fact alive, that Bearer had raised him in secret and he had been pining for a chance to exact revenge on his brother for years. At the conclusion of an epic Hell in a Cell match (one that the Wrestling Observer would give a perfect five star rating to) Kane made his debut in the WWF, costing The Undertaker the match.
The rest of the year was marred by The Undertaker chasing Michaels for the WWF World Heavyweight Championship but Kane constantly costing him the title. The storyline was that The Undertaker was refusing to retaliate because he would never fight his brother. The Undertaker lost a casket match to Michaels at the 1998 Royal Rumble when Kane interfered and locked The Undertaker in a casket and lit it one fire, again trying to kill The Undertaker. The Undertaker was revealed to not be in the casket when it was reopened after the fire was extinguished, proving again that in addition to being a great wrestler, The Undertaker possessed some magical power as well. He would return in time for WrestleMania XIV, finally confronting Kane and defeating him with three Tombstone Piledrivers. They had a rematch at Unforgiven in an inferno match, a gimmick match that had been popularized in Puerto Rico where one can only win by setting their opponent on fire. The Undertaker won when he set Kane on fire, thus ending their feud.
The Undertaker ended up having one last big go-around with Mankind at the annual King of the Ring event, defeating Mankind in a brutal Hell in a Cell match that saw Mankind thrown off the top of the cell twice. He would tag with Steve Austin at Fully Loaded, winning the WWF World Tag Team Championships over Mankind and Kane, but they would drop the titles two months later to Mankind and Kane. The Undertaker then became the number one contender for the world title and would challenge Austin at SummerSlam, losing in a thrilling match at Madison Square Garden. He then revealed that he was now tagging with his brother Kane and working for the villainous Vince McMahon in helping take the title away from Austin.
The duo, called the Brothers of Destruction, formed a devastating tag team and were an instrument for McMahon to exact revenge on Austin. After a pair of controversial matches vacated the world title, he and Austin would move on to feuding outside of the world title scene, with The Undertaker costing Austin a tournament match at Survivor Series. Kane would turn on The Undertaker again, costing him a match with Austin at Rock Bottom.
He would then be out of action for a while after undergoing hip surgery, but remained on television. He formed a stable, The Ministry of Darkness, and became a new, demonic presence, leading a cult of mid-card wrestlers to do his bidding. A full heel at this point, The Undertaker often spoke of a “higher power” and began a rivalry with Vince McMahon and his stable, The Corporation in an attempt to take over the WWF. He returned to the ring and defeated The Big Boss Man in a forgettable Hell in a Cell match at WrestleMania XV and Ken Shamrock at Backlash. It was during this period that The Undertaker would perform outlandish acts of violence, “hanging” The Big Boss Man from the Cell after their match and often performing exorcism-like rituals on other wrestlers. In retrospect these angles have aged very poorly, but at the time they were very successful in getting him over as a heel.
The Undertaker would defeat Austin for his third world title when it was revealed that he and McMahon had been in cahoots the entire time with the idea of screwing Austin out of the title, leading to a memorable promo from McMahon when he claimed to be the higher power that The Undertaker was always speaking of (It’s me Austin!!). They merged their factions, becoming The Corporate Ministry, but Austin would win the title back at King of the Ring and retain it in a First Blood Match at Fully Loaded. Frustrated with his lack of success, The Undertaker dissolved his alliance with McMahon and formed a tag team with The Big Show, which while brief, managed to win the tag titles twice. He would then miss eight months of time recovering from a groin injury and a pectoral tear.
The Undertaker returned in May of 2000 with a completely new persona. Gone was the funeral music and many of his dark personal traits, instead was “The American Bad Ass” a rebellious biker which was much closer to the actual personality of Mark Calaway. The persona was a refreshing change for Calaway and he arguably became a bigger star than ever despite abandoning the character that had made him such a big star in the first place. A babyface, he started to feud with Triple H and the McMahon-Helmsely faction, but ended up back feuding with Kane, wrestling a no-contest at SummerSlam He would receive a WWF World Heavyweight Championship shot against Kurt Angle at Survivor Series, but lost when Angle’s brother Eric interfered. Angle also managed to retain at Armageddon in December in a six man Hell in a Cell match.
In January of 2001 he reformed The Brothers of Destruction with Kane, even though that would seem like a really bad idea, and challenged Triple H at WrestleMania X-Seven, defeating him in a very good match. He and Kane would spend most of 2001 fighting a war against The Alliance as a part of The Invasion angle, eventually helping Team WWF win the winner-take-all match at Survivor Series. He then turned heel, dubbing himself “Big Evil” and defeating Rob Van Dam at Vengeance for the Hardcore Championship, becoming the only minor-singles title that The Undertaker would ever win in his career.
The Undertaker began to feud with The Rock early in 2002, but eventually ended up working with Ric Flair, who had recently been brought back after retiring when WCW closed. The Undertaker would kick the crap out of Flair in a victory at WrestleMania X-8. He would capture his fourth world title at Judgement Day, defeating Hogan for the second time in his career. His heel run was aborted in July of 2002, but he lost the WWF Undisputed World Heavyweight Championship to The Rock at Vengeance. As part of the brand extension, The Undertaker would be drafted over to Smackdown, becoming an anchor for the show until the end of the brand extension in 2011.
His first matter of business on Smackdown was to feud with new world champion Brock Lesnar. They would fight to a double-count-out at Unforgiven and Lesnar would defeat The Undertaker at No Mercy in a bloody Hell in a Cell match that would end up being one of the best matches of each men’s careers. A forgettable feud with The Big Show would follow into 2003 and he would again fail to take the title away from Lesnar. At Survivor Series 2003 he lost a Buried Alive match to Vince McMahon (McMahon had assisted Lesnar in his victories over ‘Taker) when Kane interfered, once again presumably killing The Undertaker.
He would return at WrestleMania XX, reverting back to his original Deadman persona and defeating Kane for the second time at WrestleMania. He then carried feuds with other stars for SmackDown, including the Dudley Boyz and an up-and-coming John Cena before challenging JBL for the WWE Championship at SummerSlam, which saw JBL retain via disqualification. He would challenge twice more for the title, but was thwarted each time by interference from Heidenrich, which led to a feud culminating in a casket match at the 2005 Royal Rumble, which The Undertaker won. He
then feuded with Randy Orton, defeating him at WrestleMania 21.
The feud was built upon the idea that Orton was the legend killer, and what bigger legend to kill than The Undertaker? They would continue to feud throughout most of 2005, with Orton managing to pick up wins over The Undertaker at SummerSlam and No Mercy, but The Undertaker won their final match, a Hell in a Cell match at Armageddon in December.
While Orton “lost” the feud, going toe-to-toe with The Undertaker did wonders for his career and set the stage for one of the most successful runs in wrestling over the last decade. The Undertaker’s mystique was so great by this point in his career that he didn’t even have to lose matches to put guys over, merely letting them hold their own was good enough to promote them.
After losing a World Heavyweight Championship match to Kurt Angle thanks to interference from Mark Henry, The Undertaker would defeat Henry in a Casket Match at WrestleMania 22. He would then be confronted by The Great Khali, whom in a throwback to past storylines involving The Undertaker, would prove to be a monster who The Undertaker was tasked with slaying, and Khali gave Giant Gonzalez a run for his money in being giant and a poor worker. Khali manhandled The Undertaker like nobody had ever seen before and defeated him in a match at Judgement Day. The Deadman would get his revenge however, eventually defeating Khali in a Last Man Standing match, ending their feud. He would then face another up-and-comer, Mr. Kennedy, with Kennedy winning their First Blood match at Survivor Series but losing a Last Ride match at Armageddon.
Right around this time The Undertaker would began to get serious recognition for a streak that had been developing at WrestleMania, in fact he was undefeated at the event, 14-0. From here on out, The Streak would become a big calling card for WWE, often promoting each Undertaker match at WrestleMania as equally important to the world title matches. While he would never win as many world titles as some of his contemporaries, The Streak would become his biggest legacy, consistently proving to be a tremendous draw for WrestleMania and proving the theory that The Undertaker did not need a title to draw correct.
He won his first Royal Rumble match in 2007 and would challenge then-World Heavyweight Champion Batista at WrestleMania 23, defeating him in a Streak vs Championship match. Subsequent rematches ended in draws, but following a cage match against Batista, The Undertaker was attacked by Henry and Edge cashed in his Money in the Bank contract for a title shot, defeating the exhausted champion. After taking time off, he returned at Unforgiven in September and defeated Henry. He attempted to regain his lost championship (now possessed by Batista) but was unsuccessful, eventually losing a Hell in a Cell match when Edge interfered. This ignited a feud with Edge that eventually saw them meet in the main event of WrestleMania XXIV, which saw The Undertaker win the World Heavyweight Championship for the second time in as many years.
The Undertaker was then involved in a dumb storyline where Smackdown General Manager and the kayfabe wife of Edge, Vickie Guerrero, stripped The Undertaker of his title because his submission hold, Hell’s Gate, was illegal. The Undertaker failed to regain his vacated title, eventually losing to Edge at One Night Stand but did get a win at SummerSlam in a Hell in a Cell match (Edge had already lost the title to CM Punk). He continued to feud with Guerrero and The Big Show into 2009. He then reignited a feud with Michaels, with Michaels claiming that he could end the streak because The Undertaker was never able to defeat him in a singles match. They met at WrestleMania XXV with The Undertaker retaining in a thrilling match that many fans consider the best match in company history.
After taking time off, he returned in August to feud with Punk, who was the World Heavyweight Champion at the time. He would end up defeating Punk for the title at Hell in a Cell in the eponymous match and retained it in subsequent rematches. In December of 2009, Michaels proved to be obsessed with avenging his loss to The Undertaker and challenged him to a rematch at WrestleMania XXVI. While originally declining Michael’s challenge, he accepted when Michaels cost him the world title to Chris Jericho at Elimination Chamber. This time Michaels put his career on the line and two main evented the show with another classic match that saw The Undertaker improve his WrestleMania record to 18-0. The Undertaker would return briefly later in 2010, feuding with Kane but was eventually written off television because of injuries.
By 2011 The Undertaker was pretty much done as a full-time performer. Now in the twilight of his career, he was counted on for a big match at WrestleMania but not much else. He returned in February and was confronted by Triple H, leading to a match at WrestleMania XXVII which The Undertaker won despite Triple H controlling most of the match and The Undertaker was carted off at the end of the match in a stretcher. He would come back ten months later to confront Triple H, and a Hell in a Cell match was set up for WrestleMania XXVIII, the idea being that while The Undertaker won the match, Triple H had laid a severe beating on him and he needed revenge. With Michaels called in as a special guest referee, The Undertaker overcame the treachery of Michaels and Triple H to win the match.
After another year long hiatus The Undertaker returned and defeated Punk at WrestleMania 29. The next year he was called into duty to face Brock Lesnar at WrestleMania XXX. Shockingly, Lesnar dominated The Undertaker and defeated him, ending The Streak and stunning the wrestling world. Although The Streak was over, The Undertaker proved to be a valuable commodity still for WWE. He defeated Bray Wyatt in a forgettable match at WrestleMania 31, but he would return in the summer of 2015 to avenge his loss to Lesnar, defeating him in controversial fashion at SummerSlam when he kicked Lesnar below the belt. In the final blow-off of their feud, Lesnar defeated The Undertaker at Hell in a Cell inside the Cell.
His next big feud would be a bizarre angle in which The Undertaker inexplicably was forced to wrestle Shane McMahon in a Hell in a Cell match at WrestleMania 32, with the stakes being that if McMahon won he would have control of the company and if The Undertaker lost he would have to retire. The Undertaker won, and the feud was pretty much never mentioned again on WWE television. Now 51 years old, The Undertaker is hearing grumblings about his prospective retirement and it is unclear just how much longer he is going to keep working.
The Undertaker possess a unique place in wrestling history. While he never had the championship success as guys like Ric Flair, Triple H or John Cena, he has achieved a certain level of iconic status that is unheard of in American wrestling. Really his legacy is closer to those of guys like El Santo, Giant Baba and Antonio Inoki than any of his contemporaries. Only Andre the Giant can rival the magnitude of his physical presence in a wrestling ring. His durability over the years has been outstanding, no wrestler holds quite as much respect for his toughness inside the ring as The Undertaker.
Realistically, The Undertaker’s career, up until the very end when he became a pure special attraction, was mostly taken for granted. When you think of the early-90s, you think of Hogan and The Ultimate Warrior and Randy Savage, even though The Undertaker rapidly became one of the most over guys in the company shortly after his debut. When you think of the new generation, you think of Hart and Michaels and Diesel, even though The Undertaker was the biggest draw for the company and anchored overseas tours along with Hart. When you think of the Attitude Era you think of Austin and The Rock and Vince McMahon, even though The Undertaker was the most versatile character in that group and as reputable as any of them. When you think of the Ruthless Aggression Era you think of Angle and Chris Benoit and Eddie Guerrero, even though The Undertaker was one of the best workers in the company. Probably because he never needed the titles or the promotion to be a major draw he gets a little swept under the rug; but The Undertaker has a greater legacy than anybody else in WWE history.