Originally published as the cover story of WrestleTalk Magazine issue 21
“This time the cowboy really rides away.”
The Undertaker said these evocative words at the end of the concluding episode of The Last Ride. The documentary centred on the Phenom’s quest for one last defining match, and you feel after his memorable Boneyard Match with AJ Styles this really might be the end. If that cinematic spectacular proves to really be the last ride, it brings to a close perhaps the most iconic career in professional wrestling history.
The 6-foot-10 brawler’s early career saw him winding through the territory system before a brief stop in WCW as Mean Mark Callous. Told by booker Ole Anderson “No one is going to pay money to see you wrestle.”, he made the switch to the WWE (then WWF). At a time when the Connecticut giant had prison guards, Elvis impersonators and drill sergeants on their roster, Mark Calaway was dubbed ‘The Undertaker’, a wrestling funeral director.
The 6-foot-10 brawler’s early career saw him winding through the territory system before a brief stop in WCW as Mean Mark Callous. Told by booker Ole Anderson “No one is going to pay money to see you wrestle.”, he made the switch to the WWE (then WWF). At a time when the Connecticut giant had prison guards, Elvis impersonators and drill sergeants on their roster, Mark Calaway was dubbed ‘The Undertaker’, a wrestling funeral director.
“Holy cow! Look at the size of that ham hock!” cried commentator “Rowdy” Roddy Piper, summing up the impressive physical specimen as he stalked down the aisle daubed in all-black, with the off-white facial hue of a corpse. Serving as the mystery partner for Ted Dibiase’s Million Dollar Team, Undertaker eliminated Koko B. Ware and Dusty Rhodes before being counted out.
Undertaker was fed a steady stream of enhancement talent in televised squashes. Fans would have to wait until the Royal Rumble in January 1991 to see Taker lock horns with established stars. Entering a strong showing, he eliminated Butch, Bret Hart and the Texas Tornado during his 14-minute stint. He was eliminated by the Legion Of Doom, a testament to how much stock WWE were putting in their undead prospect.
Managed in these formative stages by Brother Love, the crimson one was an odd fit for the Lord Of Darkness. Enter Paul Bearer, played by qualified mortician William Moody. Atmospheric vignettes shot on-location at real graveyards featured Bearer’s high-pitched warbling followed by the Phenom urging his opponent to “Rest In Peace”.
Undertaker eased to a four-minute victory over veteran Jimmy Snuka at Wrestlemania VII. Nobody could have predicted they were watching a performer who would define the spectacle of “The Granddaddy Of Them All”. After feuding with the Ultimate Warrior, Undertaker’s first pay-per-view main event came opposite WWE champion Hulk Hogan at Survivor Series. Undertaker would capture his first world title when Ric Flair interfered, before dropping the strap back at Tuesday In Texas six days later.
Undertaker eased to a four-minute victory over veteran Jimmy Snuka at Wrestlemania VII. Nobody could have predicted they were watching a performer who would define the spectacle of “The Granddaddy Of Them All”. After feuding with the Ultimate Warrior, Undertaker’s first pay-per-view main event came opposite WWE champion Hulk Hogan at Survivor Series. Undertaker would capture his first world title when Ric Flair interfered, before dropping the strap back at Tuesday In Texas six days later.
Despite the darkness of the character, fans began embracing the Undertaker. WWE responded by turning the spectral superstar babyface, opposite master heel Jake “The Snake” Roberts. The pair clashed at Wrestlemania XIII as Undertaker went 2-0 on the “Grandest Stage Of Them All”. WWE’s heel ranks at the time were populated with slow, lumbering giants. Undertaker would spend the next couple of years tangling with the likes of Kamala, Giant Gonzalez and Papa Shango in poor matches. The Undertaker gimmick at the time called for a deliberate pace which meshed horribly with athletes who weren’t known for their blistering bouts.
At Royal Rumble 1994, Undertaker was written off television in an elaborate angle where Yokozuna and various heels packed a fallen Deadman into a casket. The coffin was then struck by lightning, and a stunt double Undertaker ascended into the ether. This bizarre spectacle showed the scope of the Undertaker character, while the man portraying it took time off to recover from injuries.
In the Summer of 1994, Ted Dibiase claimed to have secured the services of the returning Phenom, before brining out a fake Undertaker, played by Calaway’s real-life cousin Brian Lee. The genuine article would face his doppelganger in a dreadful bout at Summerslam 94. Undertaker then floundered in sluggish bouts opposite members of Dibiase’s Million Dollar Corporation.
Solace would arrive at the turn of the year, as Undertaker was finally allowed to crawl out from under the mountain of underskilled giants he’d been lumbered with since turning babyface. The WWE champion at the time was super-worker Bret “Hitman” Hart, whose technical skillset led to superior title clashes at Royal Rumble 1996 and the following Monday Night Raw. After a satisfying Wrestlemania XII encounter with Diesel, Undertaker entered hostilities with Mankind, the former Cactus Jack portraying a dark, unhinged masked villain. The feud peaked a Boiler Room Brawl at Summerslam 96. While the action was thrilling, climaxing with Paul Bearer turning heel and siding with Mankind.
Further matches with Foley and new Bearer charge Vader were generally good, and the storyline allowed Undertaker to loosen up and show a more human side as issues with his former mentor turned personal. Cartoonish gimmicks were slowly being replaced by gritty, realistic characters. Undertaker updated his persona, pivoting from walking corpse to gothic tough guy.
Undertaker picked up another Wrestlemania win when he snagged the WWE championship from Sycho Sid. Undertaker carried the strap through bouts with Bearer’s stable before dropping it to Bret Hart in an electric Summerslam 97 main event. Guest referee Shawn Michaels accidentally drilled the Deadman with a chair, allowing the Canadian to pin him. Michaels and Taker would face off in the first Hell In A Cell match at Badd Blood. An intensely bloody and violent affair also featured the debut of Kane. Weeks before, Paul Bearer told the story of Undertaker’s brother, who was thought to have perished in a house fire. The masked behemoth, played by Glenn “Isaac Yankem” Jacobs, blasted his storyline sibling with a Tombstone Piledriver, gifting the win to Michaels.
Undertaker and Kane would clash at Wrestlemania XIV in a fondly-remembered showdown before tangling on-and-off throughout 1998. The Phenom briefly picked up where he left off with old foe Mankind, contesting the company’s second pay-per-view Hell In A Cell match at King Of The Ring. This unforgettable match saw Foley thrown mercilessly from the top of the steel structure through the announce table sixteen-feet below. Undertaker would go on to chokeslam Foley through the roof of the cage, backdrop him into thumbtacks and finally hit the Tombstone to end a savage affair. Undertaker claimed his first WWE tag team championship with rival Stone Cold Steve Austin. The uneasy pairing would drop the belts to Kane and Mankind before meeting for Austin’s WWE title at Summerslam 1998. Undertaker would come up short, and would turn heel soon after, siding with his brother Kane and Mr McMahon in their bid to take Austin’s title. The union was shortlived however, Paul Bearer turning on Kane and reuniting with the Undertaker.
Amplifying the satanic undertones of the character, Undertaker too to wearing black robes and a Luciferian goatee. Backed by the Ministry Of Darkness stable, Calaway unleashed his most outrageous performances yet. He attempted to crucify Austin, marry and then sacrifice Stephanie McMahon, and kidnap various superstars. Undertaker also captured a third WWE championship from Steve Austin at the ill-fated Over The Edge pay-per-view. Undertaker would punctuate his demonic rants with talk of a “higher power”, eventually revealed to be WWE chairman Mr McMahon, leading to a merged Corporate Ministry. Undertaker would drop the WWE title back to Austin at King Of The Ring, and the Corporate Ministry would disband. A brief partnership with Big Show followed, including two reigns as tag team champions, before injuries saw Undertaker take an extended hiatus.
During an eight month absence, the landscape of the wildly popular WWE had shifted measurably. Triple H had cemented himself as top heel, The Rock had gone supernova, and the likes of Kurt Angle, Chris Jericho and Chris Benoit had emerged. Undertaker masterfully changed with the times, swapping the funeral march for Kid Rock and his slow ringwalk for a Harley Davidson, the American Badass was born. Closer to the real-life persona of Mark Calaway, this uncompromising ass-kicker was far more relatable to modern audiences than a funeral director or satanic reverend. At Judgement Day 2000, Undertaker turned babyface by attacking Triple H and his McMahon-Helmsley regime cohorts.
Defeating his brother once again at Summerslam, Undertaker then fell to Kurt Angle in the main event of Survivor Series 2000. A month later he left another indelible imprint in the history of Hell In A Cell, by chokeslamming Rikishi off the top of the cage. He would then renew his partnership with Kane, holding tag team gold and feuding with Austin and Triple H’s Two Man Power Trip. After tangling with mostly familiar faces since his comeback, the summer of 2001 brought fresh opposition from the newly-acquired WCW .
As a decade-long WWE loyalist, Undertaker was a natural fit for a promotional war. His first opponent was former WCW champion Diamond Dallas Page. Unfortunately, rather than a dream feud between two of the biggest names of the Monday Night Wars DDP was brought in as the mystery stalker of Undertaker’s wife Sara. The seedy storyline never caught on. While Undertaker enjoyed a unified WWE/WCW tag title reign alongside Kane, his in-ring performances attracted criticism. The nadir was an awful Unforgiven clash with Kronik, so rotten that it cost the latter team their jobs. Undertaker was part of Team WWF as they bested the Alliance forces of WCW and ECW at Survivor Series to bring the Invasion storyline to a merciful end.
2002 would see an upturn in the Phenom’s fortunes. At Judgement Day he would capture the Undisputed championship from Hulk Hogan, and his reign featured a classic ladder match with Jeff Hardy on Raw. Hardy looked superb in defeat after a generous performance from our man, a world away from his selfish displays during the WCW invasion. Undertaker would drop the title to The Rock in an exciting triple threat match also featuring Kurt Angle.
Undertaker closed out the year feuding with “The Next Big Thing Brock Lesnar. Their quarrel peaked with a brutal epic inside the confines of Hell In A Cell at No Mercy. Lesnar emerged victorious as the Deadman continued to put over younger talent. He was then programmed with another wrestler targeted for main event success, John Cena. Cena tasted victory in a pair of Smackdown matches before Taker triumphed in a rewarding bout at Vengeance 2003.
The biker rode one last time into a Buried Alive match with Vince McMahon at Survivor Series 2003. Despite dominating the match from start to finish, interference from Kane led to Undertaker being buried. He did not return until Wrestlemania. At the twentieth instalment of the quintessential supershow, the man from the darkside emerged to face Kane, with a new look that borrowed from every incarnation of his character. The horror-movie effects, funeral theme music, hat and trenchcoat were paired with the MMA gloves and modern ring-style of the biker. This version of Undertaker, with occasional subtle changes, would be used for the rest of his career.
Undertaker had quietly amassed twelve wins at Wrestlemania. More an indication of the character being strongly-booked than a deliberate decision, little had been made of this undefeated run. However when Wrestlemania XXI rolled around, The Streak became a major part of Big Evil’s storyline with Randy Orton. The Legend Killer wanted to add another iconic name to his laundry list of fallen idols, vowing to end The Streak. Once again Taker gave a young opponent a performance to remember, Orton eventually falling to the Tombstone.
The Streak defined Undertaker’s remaining years with the company as he would put together an incredible body of work. While his Casket Match with Mark Henry the following year underwhelmed, Wrestlemania XXIII began a legendary run of Springtime scorchers. Undertaker faced World Heavyweight titlist Batista in a frantic war. The pair would contest a series of acclaimed rematches before Edge would cash in his Money In The Bank briefcase to snatch the Phenom’s championship. Undertaker would wear the gold again after defeating Edge in a choice match at Wrestlemania XXIV.
The Streak’s was forever cemented as the highlight of Wrestlemania in 2009, when the Undertaker faced off with Shawn Michaels. The dramatic battle featured numerous false finishes, a suicide dive onto a cameraman and the iconic image of Undertaker’s distraught face when Michaels kicked out of the Tombstone. Perhaps the greatest match Wrestlemania has hosted, an instant classic that enhanced the already iconic reputations of both men. Undertaker’s refusal when HBK requested another chance at Wrestlemania XXVI led to Michaels costing the Deadman his World championship at Elimination Chamber. Suitably provoked, he agreed to the match if Michaels vowed to retire should he lose. In another epic, Undertaker ended the career of Shawn Michaels and took his personal Mania tally to 18-0. 2010 would prove to be Undertaker’s final year as a full-time competitor. At the age of 45, and with injuries piling up, precautions would be taken to prolong the WWE’s greatest career. His full-time swansong would come in a title series with Kane, who buried him alive at Bragging Rights.
He was summoned from exile by Triple H, keen to avenge his friend Shawn Michaels. A chaotic brawl at Wrestlemania 27 summoned memories of their Attitude Era pomp. Triple H once again woke the spectre for a rematch at Wrestlemania 28. Bringing four years worth of excellent storytelling to a fitting climax, Michaels would officiate a glorious scrap inside Hell In A Cell. Taker would score the Streak-preserving win, and as the three men embraced afterwards many speculated that we had seen the last of this influential group.
Undertaker resurfaced in February of the following year at a house show, blowing off ring rust for a Wrestlemania return as CM Punk began mocking the recently-deceased Paul Bearer in an unfortunate and offensive storyline. Thankfully the tasteless hype was forgotten, and Undertaker and Punk assembled a stunner at Wrestlemania 29. The result never felt like it was truly in doubt despite the exciting action. This would be the last time one could make such a claim about Undertaker’s historic 21-0 record.
After a UK tour, Undertaker once again faded into the darkness until the following Wrestlemania, where he would meet Brock Lesnar. After three F5s, the referee would count the Undertaker’s weary shoulders down for three as the air was audibly sucked out of the Superdome in New Orleans. The Streak had fallen, the crowd fell silent, Lesnar’s manager Paul Heyman looked stunned. Fans would speculate for weeks that it had been the result of an error. WWE masterfully fueled such rumours by delaying Lesnar’s music, gravity to sink in. There was no error, Brock Lesnar had become the 1 in 21-1.
Undertaker would later reveal he suffered a concussion early in the match, and does not remember the bout. No one who witnessed it will ever forget. Fans know wrestling is predetermined, but after watching the Phenom finally fall on the stage he’d made his own, it felt all too real. This felt like a fitting end to the Undertaker legend. His function had been almost purely to defend The Streak in recent years, and with that gone it seemed like he had nothing left to prove.
Undertaker would later reveal he suffered a concussion early in the match, and does not remember the bout. No one who witnessed it will ever forget. Fans know wrestling is predetermined, but after watching the Phenom finally fall on the stage he’d made his own, it felt all too real. This felt like a fitting end to the Undertaker legend. His function had been almost purely to defend The Streak in recent years, and with that gone it seemed like he had nothing left to prove.
Enter Bray Wyatt, a swamp cult leader whose dark proclamations brought to mind those of our subject. His challenge was answered at Wrestlemania 31, where Taker triumphed after a pair of Tombstones and re-established himself as a force at the WWE’s biggest show of the year. Undertaker would return later in the year for a series of rematches with Lesnar, including another violent go-round inside Hell In A Cell.
Undertaker would contest a nostalgic stunt-fest inside Hell In A Cell with Shane McMahon at Wrestlemania 32 before a strong showing in the 2017 Royal Rumble. He was eliminated by Roman Reigns, who he would go on to face in the Wrestlemania 33 main event. The match was a disaster, however the disappointing action was forgotten in the aftermath. Undertaker laid his trademark jacket, hat and gloves down in the ring, seemingly calling time on his storied career. However Undertaker was deeply unhappy with the match and found it an unfitting finale. He entered training for another Mania return, and defeated John Cena in a three-minute match at Wrestlemania 34. The short running time raised questions about Undertaker’s remaining ring capabilities.
For the next couple of years Undertaker mainly appeared on the company’s money-spinning jaunts to Australia and Saudi Arabia. The nadir of this run was a dreadful match with Goldberg. Undertaker returned to main show storylines teaming with Roman Reigns in a win over Shane McMahon and Drew McIntyre at Extreme Rules 2019. The tag team format and no-disqualification stipulations allowed Taker the adequate protection to shine in his brightest performance in years.
AJ Styles began lobbying WWE management for a chance to face the Phenom, and a bout was agreed for Wrestlemania 36. COVID-19 put this in jeopardy, moving the pay-per-view to the Performance Center. The match would go ahead as a pre-taped Boneyard Match. Undertaker portrayed a hybrid of the American Badass, Deadman and real-life Mark Calaway. The combatants brawled around gravestones, battled on top of a barn, broke the windows of a hearse and put on a riotously entertaining show. Undertaker was victorious, burying Styles alive before riding away on his motorcycle as his flaming symbol burnt behind him. A worthy full stop on an insurmountable legacy.
Undertaker confirmed he intends to retire on the final episode of The Last Ride, finally settled in the fact his career has a worthy finale. The Undertaker character would have been an albatross for many, an overly-gimmicky relic of a bygone era. But through constant reinvention and evolving ring work, Mark Calaway has kept Vince McMahon’s greatest creation relevant for three decades. The Undertaker may never ride again, but what he did in his thirty years in the WWE will never be forgotten. Rest In Peace.