The Undertaker – Evolution Of The Phenom

The faces of The Undertaker

Over his three-decade career in WWE, The Undertaker showed himself to be one of the most versatile performers ever seen in professional wrestling. From his beginnings as a zombie mortician from the old west to a badass biker and everything in-between, The Undertaker has kept his character fresh and current through multiple eras of WWE programming. In this feature, we will look at the evolution of one of the most legendary characters to ever grace the squared circle.

The Original Deadman – 1990

The Undertaker - Funeral Parlour

On November 22nd, 1990 the World Wrestling Federation changed forever when The Undertaker strode to the ring for the first time at Survivor Series. Unlike many of the flamboyant, technicolour stars of the time, he wore black and grey and moved slowly and methodically in the ring.

For his debut, Undertaker was brought out as part of the Million Dollar Man’s team to battle The Dream Team of Dusty Rhodes, Koko B. Ware, Bret Hart and Jim Neidhart. He quickly disposed of B.Ware with a Tombstone Piledriver and later took out Rhodes with a Double Axe Handle from the top turnbuckle. While he could have continued to dominate the bout, Undertaker instead left the ring to aid his manager, Brother Love, in attacking Rhodes further, resulting in him being counted out.

“Mark Calaway at that moment is so nervous that he can barely get one foot in front of the other. This is a brand new character, and in the ring, you’ve got “The American Dream” Dusty Rhodes, you got Bret Hart, all these top-tier guys, and I’m about to basically toss them all around.

“I already knew in my head that this character was going to walk slow, but I’m so excited on the inside, I’m like, “Slow down.” And I was moving slow, but in my head, I want to get there and get started.” (H/T USA Today)

Brother Love was only to be The Deadman’s manager briefly and in February 1991 another key component of The Undertaker’s character was to be added, Paul Bearer. Much like Undertaker himself, Paul Bearer was a marked change from managers of the past. Wearing dark suits and pale make-up, Bearer screamed in an almost inhumanly shrill voice during his charge’s matches. He also carried an urn which he used to ‘recharge’ The Undertaker when it seemed like the tide was turning against him.

With Bearer by his side, Undertaker continued to run roughshod over every opponent thrown at him – including getting his first WrestleMania win against ‘Superfly’ Jimmy Snuka – and a year after his first appearance, he found himself facing Hulk Hogan for the WWF Championship. While the future Phenom seemed unstoppable for most of the match, he turned the tide and looked to be on the verge of victory when Ric Flair appeared at ringside to offer a distraction. This gave the challenger enough time to get back up and he soon delivered a Tombstone to Hogan on a chair placed in the ring by Flair to claim his first world title.

Although his reign proved to be short-lived, with Hogan recapturing the gold just over a week later, Undertaker had cemented himself as a force to be reckoned with.

For the next few years, Undertaker engaged in feuds with future Hall of Famers like Jake ‘The Snake’ Roberts, Kamala, and Yokozuna. The most memorable bout with the latter came at the 1994 Royal Rumble when ‘The Man from the Darkside’ challenged Yokozuna for the WWF Championship. The match ended when a group of heels came out to aid the champion in sealing his challenger inside the casket. Smoke then came from the coffin and The Undertaker appeared on a video screen from within it, ominously announcing that “Soon all mankind will witness the rebirth of the Undertaker. I will not rest in peace.” before appearing to ascend high into the rafters.

Darkness Era – 1994

The Undertaker - Purple

That rebirth came seven months later at SummerSlam 1994. Prior to the event, Ted DiBiase had claimed he would bring The Undertaker back to the WWF, however, the man he introduced was an imposter. Paul Bearer called him out and promised to bring the real deal back to face his doppelganger.

When the one, true Undertaker made his entrance at the event, he had reinvented himself for the first time. The drab greys of his old outfit had been replaced with purple and he entered to the sounds of thunder while being bathed in the blue/purple light that would become closely associated with him for the rest of his career. The revitalised Deadman made short work of The Underfaker, delivering three Tombstones to show that he was not only back, but more dominant than ever.

Over the next few months, Undertaker defeated all of the heavy-hitters in DiBiase’s Million Dollar Corporation including IRS, King Kong Bundy, and finally, Kama (aka The Godfather).

With DiBiase dealt with, he moved onto rivalries with Yokozuna and Mabel. It was an errant punch from Mabel that shattered The Phenom’s orbital bone, leading to a several-week absence and a short-term – but fondly remembered – change in Undertaker’s look as he donned a Phantom of The Opera-style mask to protect the injured eye.

The Undertaker wearing mask

It was during this period that The Undertaker began one of the most intense and violent feuds of his career as he was targeted by the debuting Mick Foley under the guise of the deranged Mankind. Foley’s tactics included ambushing Undertaker in backstage areas, interfering in matches, and even costing him a chance at the Intercontinental Championship. When the two finally met in the ring at King of the Ring 1996, Mankind was victorious after Paul Bearer accidentally hit his long-time charge with the urn, allowing Foley to lock in the Mandible Claw.

Things between the two continued to escalate and eventually culminated in a Boiler Room Brawl at the 1996 SummerSlam. They went to war, showing no mercy as they battled in the arena’s boiler room and corridors, before finally reaching the ring. However, as The Undertaker reached towards Paul Bearer for the urn – which would signal the end of the match – the unthinkable happened as Bearer turned his back on his former ally before joining Mankind in assaulting him in the ring.

The Undertaker sought revenge on Mankind with an innovative new bout suited to his persona, a Buried Alive match where the goal was to literally bury your opponent. The October ‘In Your House’ pay-per-view was themed around the much-anticipated clash, with a grave having been dug in a specially brought in mound of dirt.

After another violent brawl, Undertaker put Mankind to the bottom of the grave with a chokeslam and shovelled dirt on him for the victory. However, things didn’t end there as The Executioner appeared and rescued Mankind from being buried deeper. As Paul Bearer watched on they turned the tables and began burying The Undertaker.

Soon, more heels ran out from the locker room to assist as the lights flashed and thunder could be heard, once the grave was full, everyone left. The camera lingered on the tombstone and a bolt of lightning struck before the gloved hand of The Undertaker shot out of the ground, showing that he was down but not quite out.

Undertaker's hand comes out of grave

The Lord of Darkness – 1996

The Undertaker - Druids

When The Undertaker came to get his revenge on Mankind once more at Survivor Series 1996, he had once again updated his image. Dropping the oversized gloves and any hint of colour, he descended from the rafters with a bat-wing style cape and wore all-black leather ring gear. This new, less cartoonish, Undertaker vanquished Mankind yet again as he and the WWF entered the edgier and more adult-oriented Attitude Era.

Over the following months, Undertaker made alterations to his ring gear and adopted the medieval style most associated with this period and turned his attention back to the WWF Championship. Appropriately, it was at WrestleMania 13 in 1997 that he captured the gold again when he defeated Sycho Sid.

The Undertaker successfully defended the title against the likes of Vader, Farooq, and Steve Austin. However, something even more important than even his second title reign was about to change the career of The Lord of Darkness forever when Paul Bearer revealed his darkest of secrets.

Bearer claimed that when Undertaker was young, he burned down his home with his family inside, killing both his parents and younger brother. However, Bearer later revealed that his brother, Kane, had survived, albeit with horrific scarring, and was coming for revenge.

At Badd Blood that October, Undertaker and Shawn Michaels intended to end a lengthy rivalry inside the first-ever Hell in a Cell match. However, that was when Kane decided to strike, making his way to the ring just as Undertaker looked to be on the verge of victory. Kane tore the cell door off its hinges and attacked his astonished brother, delivering a Tombstone to hand the victory to Michaels.

For months, Kane ran roughshod through the WWF roster much like his brother had done years prior, all the while demanding a match against The Phenom. However, Undertaker refused, saying he had promised his parents that he would never fight his own flesh and blood.

At the 1998 Royal Rumble, Kane locked Undertaker in a casket before setting it on fire, seemingly trying to end his life. This proved to be a step too far, as when The Demon of Death Valley returned two months later, he finally challenged Kane to a match, saying he would now “Walk through the fires of hell” to face him.

The two met in the ring at WrestleMania 14 and Undertaker overcame Kane, but only after three huge Tombstone Piledrivers. This was only the first of dozens of matches the pair would have in the following decades in a rivalry Undertaker recently called the greatest of his career.

“I am going to say probably the battles with Kane, I think. It was just, I think a storyline that people, whether you were a wrestling fan or you weren’t, you understood just because of sibling rivalries. And I think people identified with that. Kane was always such a physically dominant athlete, that he always brought the best out of me.” (H/T Wrestling Inc)

This period of The Undertaker’s career also saw one of the most infamous matches in the history of WWE as he resumed his feud with Mankind and the pair met in a Hell in a Cell match at the 1998 King of the Ring. In one of the most brutal bouts ever seen, Mankind was thrown off the top of the cell and later Chokeslammed through the top of the structure.

As 1998 wore on, The Undertaker continued his pursuit of the WWE Championship, getting a chance to capture the gold from Steve Austin at that year’s SummerSlam but ultimately being defeated. By this point, he had joined forces with Kane and the two revealed that they were aiding Vince McMahon in his goal to get the title away from Austin. This led to a Triple Threat match that September where the brothers pinned ‘The Texas Rattlesnake’ simultaneously, resulting in the title being vacated and a match being set between the Brothers of Destruction to crown the champion with Austin acting as referee.

During the match at Judgment Day that October, Paul Bearer turned on Kane, assisting Undertaker in attacking The Devil’s Favourite Demon with a steel chair. However, Austin refused to count the pin-fall, instead attacking Undertaker and counting both men out.

The following night on Raw, The Undertaker and ‘Brother Paul’ revealed that not only had they reconciled after years of animosity, but they were bringing their ‘Ministry of Darkness’ to “unleash a plague” on WWE.

The Ministry of Darkness – 1998

The Undertaker - Attitude Era Champion

The Ministry of Darkness era brought a new level of evil to The Undertaker character. Taking on the role of a dark cult leader, he grew his goatee further and began wearing black robes when not in the ring. He also had his own throne, stylised after his symbol.

In the lead up to a Buried Alive match against Austin at Rock Bottom in December 1998, The Lord of Darkness lived up to his moniker more than ever, kidnapping the champion and crucifying him a giant version of his symbol and trying to have him embalmed. Austin got his revenge by defeating Undertaker yet again, this time with some help from Kane and a huge digger which dropped soil on top of The Deadman once he was in the grave.

Following his return, The Undertaker set about recruiting members for his new Ministry, first the team of The Acolytes – Farooq and Bradshaw. The two were instructed to kidnap Dennis Knight, who Undertaker performed a ritual on to turn him into his servant, Mideon. At the 1999 Royal Rumble, Mideon and The Acolytes kidnapped King of the Ring winner Mabel who was converted into Viscera, dropping his previous purple outfits for a black jacket and wearing white contacts. Finally, the already gothic trio of The Brood – Gangrel, Edge and Christian – were revealed to be members of the group, completing the line-up.

Undertaker then revealed his true intentions were to completely take over WWE at the behest of an unseen ‘Higher Power’. This meant a lengthy feud with Vince McMahon and his Corporation faction. Undertaker went to great lengths to get inside the head of McMahon, burning an Undertaker symbol on the grounds of his home and threatening his daughter Stephanie. In one of the more infamous storylines of Undertaker’s career, following Backlash in 1999, he kidnapped Stephanie before strapping her to his symbol and attempting to perform a “black wedding” only for Austin to interfere with the ceremony and rescue the youngest McMahon.

Following Austin’s actions, Undertaker was granted a title match against The Bionic Redneck at Over the edge 1999, this time with Shane McMahon as the special guest referee. Undertaker won the bout with the help of McMahon, capturing the gold for the third time in his career.

Shortly after, Shane McMahon took control of The Corporation from his father and the group merged with The Ministry of Darkness to form The Corporate Ministry. It was soon revealed that the so-called Higher Power had been Vince McMahon and the entire saga had been another of his plots to get at Steve Austin, although this time the McMahon family had been collateral damage.

“It was a huge storyline. I wasn’t a big proponent of the higher power being Vince. I just thought it watered The Ministry down; although, it led to me abducting Stephanie and all of that. It all works out. But, you know, originally I wasn’t real thrilled about the Corporate Ministry. That really felt watered down to me. I felt like it kind of took away from what we were doing. Although, as I said, we got it back,” Undertaker said.

“But, you know, anytime you can be involved in a storyline with the boss, you know you’re going to get a lot of eyes on you. So, yeah, it all worked out.” (H/T Cultaholic)

The Undertaker lost the WWE Championship back to Austin late in June, leading to a rematch under First Blood rules at Fully Loaded which ‘The Deadman’ lost when Austin busted him open with a television camera. Following this loss, the Corporate Ministry began to dissolve and Shane McMahon made it official during a promo on Raw at the beginning of August.

For the next few months, The Undertaker teamed with Big Show in an ‘Unholy Alliance’. The duo won the Tag Team Championships twice but the team came to an end when Undertaker suffered injuries that would put him on the shelf for several months. When he returned, he would be a very different man.

The American Badass – 2000

The Undertaker - American Badass

After an eight-month absence from WWE and following several weeks of vignettes hinting at his return, The Undertaker came back to WWE at Judgment Day 2000, interfering in the Iron Man WWE Championship match between The Rock and the reigning champion, Triple H to even the odds as The Great One was fighting off the entire McMahon-Helmsley Regime headed by Triple H and Stephanie McMahon. Unfortunately for The Rock, the referee only saw Undertaker attacking Triple H and called the last fall for The Game, allowing him to keep his title.

The Undertaker had undergone the most radical transformation of his career so far. The dark robes, funereal music and slow walk to the ring were gone, instead, he rode to the ring on a Harley Davidson to Kid Rock and was decked out in denim, a leather trench coat, sunglasses and a bandana. The ‘American Badass’ era had begun.

“So the American Badass, several things were going on there. One, yeah I got hurt. I injured my groin then right close to coming back from my groin injury, I tore a pec. So I was out most of that whole year leading into the American Badass. But what was going on was the Attitude Era. You’ve got Stone Cold, who’s cutting these incredible promos, that people can really identify with. It’s like real life with a little bit of gas behind it. You’ve got the Rock cutting these unbelievable promos. All these promos are just, they are so good.

“I think, I would have survived but I wouldn’t have thrived if I had not taken a break. As good as the character is, you’re kinda boxed in too, with what you can do and what you can’t do. You know, it’s hard for the Undertaker to be in the ring while The Rock is talking about poontang pie, and to have some kind of retort that The Undertaker could give. So, it was a period for me to, just to take a deep breath and do something different for a minute” (H/T

During this time The Big Dog presented a more human side to himself, both through doing longer promos that revealed more of the real man behind the character and by introducing his family in the form of then-wife Sara.

He feuded with the McMahons for some time and teamed with Kane and the Rock to defeat Vince, Shane, and Triple H at that year’s King of the Ring. The match featured the unique stipulation that if the face team won, whoever got the pin-fall would be awarded Triple H’s WWE Championship. Unfortunately for The Undertaker, it was The Rock who would pin Vince McMahon to get the gold.

This was not the end of Undertaker’s quest for the title though, and he went on to unsuccessfully challenge Kurt Angle for the Olympic Gold Medallist’s newly won Championship before being part of the first 6-Man Hell In A Cell match at Armageddon. Though the bout was memorable for Undertaker pushing Rikishi from the top of the cell, he was once again unable to claim the title.

Following the defeat, the Brothers of Destruction reformed, winning the Tag Team Championships and entering a feud with the ‘Two-Man Power Trip’ consisting of Triple H and Steve Austin. At 2001’s Backlash, The Game and Stone Cold captured the tag titles in a ‘Winner Take All’ match where their Intercontinental and WWE Championships were also on the line. The feud continued into Judgment Day, where Kane defeated Triple H to become the Intercontinental Champion while Undertaker lost to Austin.

Soon after the feud ended, Undertaker became embroiled in the Invasion storyline, first defeating Diamond Dallas Page who had been stalking his wife and later joining Team WWE to help inflict the final defeat on the WCW/ECW Alliance at Survivor Series.

Big Evil – 2001

Towards the end of 2001, The Undertaker turned heel when he forced JR to join Vince McMahon’s ‘Kiss My Ass Club’ by ramming him into the WWE Chairman’s exposed cheeks. Following the turn, he changed his appearance again, cutting his hair short for the first time in his career and dyeing it jet black. This was accompanied by a character change that saw him becoming more violent.

Among other acts of aggression, Big Evil decimated Maven after the Tough enough winner dropkicked him out of the 2002 Royal Rumble match, beat up Ric Flair’s son David in a bathroom when he was feuding with his father, and tied Hulk Hogan to the back of his motorbike and dragged him around the backstage area during an episode of Raw before going on to beat ‘The Hulkster’ for the WWE Undisputed Championship at that year’s Judgment Day.

After carving a brutal path through WWE for the first half of 2002, a turning point came that July when Jeff Hardy challenged The Undertaker to a Ladder Match for his title. Despite the sadistic biker throwing everything he could at Hardy, the young star refused to quit and kept getting back up. In the end, The Undertaker was finally able to put Hardy down long enough to climb the ladder and grab his title before giving him one final Last Ride.

However, Hardy was still able to pull himself to his feet once more to the shock of The Undertaker. Taker returned to the ring, but instead of continuing the assault, he raised Hardy’s hand as a sign of respect, marking his return to being a babyface. Soon after, he lost the championship to The Rock at that year’s Vengeance PPV.

For the remainder of his time as Big Evil, The Undertaker entered an on and off feud with Brock Lesnar, facing him in violent Hell in a Cell and Biker Chain matches with ‘The Beast Incarnate’ invariably coming out on top. The Biker Chain bout ended with Vince McMahon pushing Undertaker off the top rope and allowing Lesnar to take another victory.

McMahon’s interference kicked off a feud with Undertaker that led to the two having a Buried Alive match at Survivor Series. During the match, Kane unexpectedly came to the aid of the WWE Chairman, throwing Undertaker into the grave and allowing McMahon to bury him with the help of a front loader.

While Kane claimed The Undertaker was “dead and buried forever” following the match, it soon became apparent that he was only half-right.

Resurrection of The Deadman – 2004

The Undertaker - WrestleMania XX

At the 2004 Royal Rumble match, The Undertaker began to make his presence felt again. As Kane was dominating everyone in the ring the counter went to zero for the next entrant only for the lights to go out and a gong to ring out. While The Phenom was nowhere to be seen, it provided a long enough distraction for a shocked Kane to be thrown over the top rope by Booker T.

The supernatural occurrences continued over the following weeks with Kane being bathed in The Undertaker’s signature blue light, rained on in the ring, and being attacked by lightning bolts. Finally, a coffin appeared in the ring which Kane found contained Paul Bearer’s signature urn. A video then played proclaiming that at WrestleMania 20, the dead would rise again and a match between The Undertaker and Kane was set.

At the event, once Kane was in the ring the lights went out and the familiar voice of Paul Bearer sounded through Madison Square Gardens for the first time in years. He carried the urn to the ring followed by druids. Then The Undertaker’s old funereal music played and The Deadman returned from the grave.

This version of The Undertaker had several tips of the hat to past incarnations. Presented like an Old West gunslinger, he wore a leather trench coat and MMA gloves like the American Badass, but the traditional headwear of the original Deadman. The bike was now gone and the blue light and smoke had returned to his entrance.

Only months after his return with Bearer by his side, Paul Heyman and The Dudley Boyz kidnapped Undertaker’s friend and ally and threatened to bury him in concrete if he didn’t lie down and accept a loss from the legendary duo at The Great American Bash in what was dubbed a Concrete Crypt Match. Undertaker refused to lie down, instead defeating the pair and then preventing Heyman from burying Bearer.

However, in a shocking move, he dropped the cement on Paul Bearer himself after telling him he had “no other choice” following the Dudleyz and Heyman showing he was The Undertaker’s weakness.

During this period, The Undertaker was still exclusive to SmackDown where Teddy Long was the General Manager. Long famously played on The Man from the Darkside’s role as the conscience of WWE by sending various heels his way by announcing they would “Go one on one with The Undertaker!”

Besides these regular outings which saw Undertaker dominate his opponents, he also continued his quest for the WWE Championship, although he often lost opportunities due to shenanigans from various heels like JBL, Booker T, and Randy Orton.

A lengthy feud against Orton and his father, Bob Orton, in 2005 led to some tweaks to his character. After the father and son defeated Undertaker in a Casket Match, they locked him inside the coffin and set it on fire. He was not seen again until Survivor Series when he emerged from a coffin to try to get his hands on the Orton’s.

Now, he had reverted his outfit to the spandex tights he wore for the pre-biker portion of his career emblazoned with his logo. He also began using the Tombstone and Chokeslam more again in place of the Last Ride which he had adopted during the Badass era. He finally got his revenge on Randy Orton by defeating him in a Hell in a Cell match at that year’s Armageddon.

After feuds with Kurt Angle, MVP and King Booker during 2006, The Undertaker entered the 2007 Royal Rumble match and went on to win the bout for the first time in his career. He would go on to face Batista for the World Heavyweight Championship at WrestleMania 23, capturing that title for the first time. Unfortunately, his reign was cut short by Edge, who cashed in his Money in the Bank contract a few weeks later to take advantage of Undertaker after he survived a Steel Cage against Batista. In reality, the Demon of Death Valley had to take time off for torn biceps.

On his return, The Undertaker began pursuing the World Heavyweight Championship again, eventually getting his shot against Edge at WrestleMania 24, where he took the gold from the Rated-R Superstar in the main event. Edge was able to regain the title several months later with assistance from Vickie and Chavo Guerrero.

It was around this time that, although still appearing regularly for most of the year, The Undertaker began taking lengthy absences from the ring for several months at a time. When he was actively competing, however, he was often involved in the main event scene and had feuds with figures like Big Show and Triple H.

The Phenom’s WrestleMania undefeated streak started becoming more and more of a focus. While it had been acknowledged on TV before, it really came to the fore during his feud with Shawn Michaels leading into 2009’s WrestleMania 25 as The Undertaker had never been able to defeat Michaels in a singles match before then.

This led to an all-time classic at the event between the two – which many regard as the best match of all time – with the Deadman emerging with his streak intact. The loss ate away at HBK for much of the following year and he began demanding a rematch as he was sure he could overcome Undertaker. In the end, he put his career on the line against the streak at WrestleMania 26, only for the Deadman to defeat him again, bringing his iconic run to an end.

By the time of WrestleMania 27, the annual defence of the streak had become as much a WrestleMania tradition as the singing of America The Beautiful and each year The Undertaker’s entrances became more elaborate and he wore unique entrance gear for every match, adding to the big match feel of his bouts. A selection of these can be seen on

That year, he defeated Triple H for the second time on The Grandest Stage Of Them All and at WrestleMania 28 he made it three for three against The King of Kings in a match refereed by Shawn Michaels and billed as ‘The End of an Era’ bringing the streak to 20-0.

Undertaker overcame CM Punk at WrestleMania 29 following a feud that became hugely personal as Punk and Paul Heyman insulted the memory of Paul Bearer, who passed away only weeks before the event in March 2013. However, it was the following year that would see him face his greatest challenge yet as he was set to face The Beast Incarnate, Brock Lesnar, for the first time in over a decade.

At the 30th anniversary of WrestleMania, the unthinkable happened, despite kicking out of the F5 twice, The Undertaker was unable to respond to the third, ending his streak at 21-1, a record that may never be beaten.

“Obviously, in Vince’s mindset, if it’s not Brock, then who? My biggest concern was I just wanted to make sure that [McMahon] was sure, and that’s what he wanted to do.

“I didn’t feel like Brock needed it. Brock was already a huge star, and it wasn’t going to help him one way or another. My only concern was there might have been someone down the line that could have benefited from it more, and that probably would’ve been Roman later on.

“That’s with hindsight being 20/20. But if I was going to get beat by someone, Brock was a guy who had the credentials, I think, to do it, and people would be like, ‘Um, okay, s**t, that’s Brock Lesnar.’ That was my biggest deal. I just wanted to make sure that’s really what [McMahon] had wanted to do.” (H/T CBS Sports)

Despite losing the streak, Undertaker continued to perform at WrestleMania and while he was able to rack up victories over Bray Wyatt, John Cena, and Shane McMahon, there were two more losses to come. The first was against Roman Reigns at WrestleMania 33, and the other was to be the final match of The Undertaker’s storied career, the Boneyard Match against AJ Styles.

The Unholy Trinity – 2020

The Undertaker - Boneyard

By the time WrestleMania 36 came around in 2020, The Undertaker had lost a step and it was something he was well aware of. Footage was already being filmed for The Last Ride documentary series in anticipation of his retirement and The Phenom had decided it was time to pull the trigger.

The Undertaker returned earlier than usual that year, making a surprise appearance at Super ShowDown in Saudi Arabia that February and winning the Tuwaiq Trophy Gauntlet by last defeating AJ Styles. This kicked off a rivalry with Styles which became increasingly personal as The Phenomenal One began referencing Undertaker’s real-life wife Michelle McCool and talking directly to Mark Calaway. This led to him delivering warnings to Styles as Calaway and finally a cinematic Boneyard Match between the pair was the main event of night one of WrestleMania 36.

For this match, The Undertaker had been pushed to the limit of his anger and brought out his final gimmick, a combination of The Deadman, American Badass/Big Evil, and Mark Calaway himself, dubbed ‘The Holy Trinity’. Wearing black leather and a bandana, Undertaker rode to the abandoned ranch where the match was to take place on his motorcycle.

The match itself was a brawl that involved Undertaker having to take out Styles’ allies Luke Gallows and Karl Anderson as well as hostile druids before finally getting his hands on Styles himself.

The two battled throughout the huge set with highlights including Undertaker Chokeslamming Styles through the roof of the building, and Styles hitting Undertaker on the back with a literal tombstone, as well as Undertaker using supernatural trickery one last time to appear behind Styles when he thought he was about to bury him alive. For the finale, the pair ended up at the graveside again, but this time The Undertaker booted Styles into it and dropped dirt on him for one last victory before riding off into the night.

“Obviously, we always envisioned this match happening in a live arena. Somewhere in the last couple of weeks, we didn’t even know what was going to happen the next day. The idea was thrown at me at doing something off-site. I was like, yeah, that’s a much better option than trying to have a match that AJ and The Undertaker would have inside an empty arena. In our case, we were very fortunate to go off-site and do what we did.”

“The final product — I couldn’t be more proud of it. Under the circumstances, all the different things going on, everybody pulled together and put something like that out there that was different and was intriguing. I can’t speak for AJ, but I’m very proud of what we did.” (H/T Wrestling Inc.)

Final Farewells – 2021-2022

The Undertaker - Final Farewell

Following the Boneyard Match, the Last Ride documentary series chronicling The Undertaker’s last few years aired and The Deadman announced that his iconic career was officially over.

At Survivor Series 2021, exactly 30 years after he debuted in WWE, it was time for The Lord of Darkness to say his final farewell. Coming out in an elaborate jacket and classic hat, The Undertaker took a microphone to tell the Creatures of the Night that the time had come to let him “rest in peace” before walking away and giving a one-fisted salute for the last time before leaving the arena.

In 2022, Mark Calaway headlined the WWE Hall of Fame ahead of WrestleMania 38. Unlike his character, Calaway had many words and, surrounded by his past costumes, he gave an emotional hour-long speech about his career and the people who helped him along the way. In true wrestling fashion, however, he said three final words before leaving:

“Never say never”

The Undertaker WWE Hall Of Fame