10 WWE Stars The Undertaker Was Friends With (And 10 He Couldn't Stand)

There may be no wrestler with greater longevity, ability to evolve, loyalty to a single wrestling promotion, and universal respect among his colleagues than The Undertaker. While the guy hasn’t worked full time for WWE for quite a while now, he has remained an ominous figure on the landscape of the largest wrestling promotion in the world for nearly three decades, won seven world championships, and main evented WrestleMania four times while assembling a win-loss record without peer at 24-2.

Away from the ring? The Undertaker was respected enough to be agreed upon by his peers to serve as the judge for Wrestler’s Court—a mechanism for bringing wrestlers who had committed various infractions to justice. Moreover, it’s nearly impossible to find a figure in sports entertainment with anywhere near his longevity with so few detractors. Remarkably enough, on top of all of this high regard and these accomplishments, he’s also that rare wrestler to have maintained his privacy, mostly maintaining kayfabe and rarely appearing or speaking in public out of character. Only recently has he become a more regular figure in even WWE’s own documentary projects.

The Deadman’s peers haven’t been quiet, though, and stories about him have made it out to the fans. Through these tales and interview comments, we can glean some of the Phenom’s real life friends, as well as those colleagues he didn’t get along with so well. This article looks at ten of his friends and ten people in wrestling he couldn’t stand at one time or another.

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20 Friends With: The Fake Undertaker

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For all of the celebrated rivalries and storylines of The Undertaker’s epic career, one of the ones to garner the least fanfare was the feud between The Undertaker and a fake version of The Undertaker brought in by Ted Dibiase, which culminated in the main event match of SummerSlam 1994. The angle was silly, the match itself was totally forgettable, and in the aftermath, The Deadman’s antagonist simply disappeared as WWE didn’t seem interested in lingering on a failed angle.

The man who played the Fake Undertaker was actually Brian Lee, best known as a star for Smoky Mountain Wrestling and Extreme Championship Wrestling, and who later played Chainz for the Disciples of Apocalypse during WWE’s gang warfare angle in the Attitude Era. The idea of him playing The Phenom’s doppleganger reportedly came up because he was real life friends with The Undertaker and, when they were in the same place at the same time comments abounded about the two of them looking a lot alike.

While conventional logic would have had The Undertaker return to action against Yokozuna—the man who had put him out in kayfabe—Vince McMahon and company decided that The Undertaker vs. Undertaker match would provide a suitably epic return program with a paranormal, surreal feel. The Phenom’s revenge against Yokozuna was deferred to Survivor Series that fall.

19 Couldn’t Stand: Shawn Michaels

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By the end of Shawn Michaels’s career, it appears that The Undertaker shared a mutual respect with HBK as a fellow veteran who had stood the test of time and emerged a truly elite sports entertainer. This admiration between the two men set them up for an epic two match arc at WrestleManias 25 and 26.

Years earlier, however, the two men each hit career peaks around the same time, in the early years of the Attitude Era. While Michaels was the de facto leader of The Kliq with Razor Ramon, Diesel, Triple H, and The 1-2-3 Kid, The Undertaker was at the fore of The Bone Street Krew. This less serious faction that also included Yokozuna, Rikishi, Savio Vega, and Henry Godwinn played dominose together and mostly stayed out of politics. They were, nonetheless, allies to one another backstage.

Besides belonging to different groups of friends, The Undertaker reportedly took issue with Michaels’s attitude.

A widely circulated story suggests that, at the last minute, Michaels tried to back out of dropping the WWE Championship to Steve Austin at WrestleMania 14, despite having a back injury that was going to force him out of action anyway. The Undertaker reportedly confronted Michaels to make sure he did business the right way. The beef may have had its roots a half year earlier, when The Undertaker felt Bret Hart was in the right during the Montreal Screwjob, and was dubious of HBK’s innocence in that affair.

18 Friends With: Bret Hart

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While The Undertaker is committed to protecting his character, and historically dodged cameras and public sightings, one need look no further than Bret Hart’s book, Hitman: My Real Life in the Cartoon World of Wrestling to catch a glimpse of the Deadman in street clothes, seeing the sights on international tour with his friend Bret Hart.

Indeed, it seems that The Deadman respected The Hitman completely for his in ring talent and generalship, which facilitated some of The Undertaker’s best matches up to that point in his career. Moreover, The Phenom seemed to respect Hart as an ethical locker room leader. It’s a part of why he took up for Hart during the Montreal Screwjob, as referenced above. By Hart’s account, The Dead Man went so far as to physically escort Vince McMahon to the locker room to talk to The Hitman in the aftermath of the Screwjob, facilitating Hart punching his lights out.

In the end, Taker and Hart are a pair of guys from a similar era in the wrestling business who each rose to unexpected stardom, and each seemed to have similar views on protecting the business, and ultimately putting the good of storylines and the locker room ahead of their personal gain. As such, it’s little surprise the two would wind up good friends with one another.

17 Couldn’t Stand: The Big Show

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When it comes to thinking of great big men from WWE’s last 30 years, you’d be hard pressed to find two names more loyal and with greater longevity than The Undertaker and The Big Show. The two of them had their matches opposite one another, and they had a period working together as a tag team. To listen to them today, the two seem to respect one another, too, with The Big Show in particular crediting The Dead Man for mentoring him on life in the business and the WWE style.

While The Deadman may well get along with The Big Show nowadays, there are a variety of accounts to suggest that he did not much enjoy working with him when they were first put together during Show’s first year with WWE.

The Big Show came from the less disciplined, less organized world of WCW. By his own account, Show didn’t even maintain a workout regimen then, instead relying on his natural size, athleticism, and metabolism to keep him looking like a monster. The Undertaker was reportedly offended at Show’s lack of a work ethic, and lack of fundamentals as a wrestler and responded by verbally lacing into him mercilessly after their every trip to the ring. Show suggests that WWE set this up as a mentorship and, as hard as it was, he owes much of his career success to the lessons The Deadman taught him.

16 Friends With: JBL

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The careers of The Undertaker and JBL intersected in unexpected ways across the lengths of their respective tenures with WWE. After earlier gimmicks failed him, Bradshaw wound up half of The Acolytes tag team under The Dead Man’s tutelage with the Ministry of Darkness. Years later, JBL would be playing a conservative captain of industry who’d stumbled his way into a WWE Championship, and The Undertaker would be one of his primary face challengers.

In real life? Over the course of their years sharing a locker room, The Deadman and JBL were good friends.

The two were close enough that JBL notably had The Phenom as a groomsman for his wedding, with photos capturing The Undertaker and Ron Simmons flanking the proud groom on either side on his wedding day all three of them uncharacteristically clad in tuxedos for the special occasion.

Interestingly, despite their friendship, JBL has noted on the WWE Network’s Bring it to the Table that he still calls his friend “The Undertaker” as a show of respect for how seriously he takes the business and his persona. He brought that point in shouting down wrestling pundit Peter Rosenberg for daring to refer to the The Deadman by the less formal “Taker.”

15 Couldn’t Stand: Chris Jericho

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At the end of the day, The Undertaker and Chris Jericho are well established veterans and two of the biggest stars in WWE history who reportedly respect one another. They didn’t always get along so amicably, however, particularly when Jericho first surfaced in WWE.

Y2J debuted after a run with WCW that was well received by critics, but during which he didn’t get all that many opportunities from management. He had the experience of traveling the world behind him, though, having started out in Canada only to assimilate different wrestling styles from throughout the US, Japan, and Mexico before getting his primetime opportunities. Thus, when he showed up in WWE, Vince McMahon seemed to understand he had a guy with real star potential on his hands.

Jericho debuted by famously interrupting a promo by The Rock. The next target of his aggressions? The Undertaker.

Y2J called The Undertaker boring. As he describes it in his second book, Undisputed, he was telling the truth, because he was going after The Deadman immediately following a failed promo that The Phenom himself knew had run too long and wandered too much to keep the audience’s attention. For a new arrival like Jericho to call the most respected man in the locker room boring, however, was a huge faux pas that placed major heat on Jericho early in his WWE career.

14 Friends With: Shane McMahon

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2016 saw Shane McMahon make one of the most shocking returns in WWE history. After eight years absence from WWE TV, and having legitimately left the company to pursue his own business interests, Shane-O-Mac returned to Raw unannounced during the build to WreslteMania 32. He immediately got into an issue with his father, Vince McMahon and his sister Stephanie McMahon, centered on a very meta power struggle for control of the company. Shane’s father immediately set up a wager with his son, that if he could win a match at WrestleMania, he’d give him control of Monday Night Raw. The only catch? Shane would be wrestling The Undertaker, and that match would take place inside Hell in a Cell.

From a storyline perspective, Vince stacked the deck against his son. In reality, though, Vince was largely gifting Shane a perfect situation in which to come back.

Sure, there was the Cell itself, which set up the younger McMahon for one of his signature high spot stunts as he leapt off the top of the cage late in the match. Additionally, though, he was putting Shane in the ring with a dear and trusted friend.

The Undertaker had lost some of his WrestleMania status after losing to Brock Lesnar and then having a lackluster comeback match against Bray Wyatt. So, as Taker tried to get his mojo working again, and Shane returned after such a long time away from the business, the two friends cooperated closely to plan out and practice a match to make them both look good.

13 Couldn’t Stand: Mabel

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One of the uncomfortable realities of The Undertaker’s WWE run is that his size, credibility, and often as not supernatural aura made him a natural fit for WWE to book opposite fellow big men monsters. There were times when that worked out, as The Dead Man was instrumental in getting The Great Khali over, his match with King Kong Bundy at WrestleMania 11 was a bit of an intergenerational dream match, and the best of his battle of Kane put two evenly matched monsters in each other’s paths for some terrific big man battles.

Mabel represented one of the least savory monsters to come The Undertaker’s way.

After a stint as half of the Men on a Mission tag team, WWE got serious about the five hundred pounder, booking him as an upper card to main event heel off of his 1995 King of the Ring tournament victory. After a summer long program with Diesel that culminated in a historically bad SummerSlam main event, Mabel transitioned to feuding with The Dead Man.

Mabel wasn’t the most capable dance partner for The Undertaker, but far worse than that, his recklessness paired with his super heavyweight size made any accident he made exceptionally dangerous. A misplaced leg drop to The Phenom shattered his orbital bone and forced him to wrestle with a mask In the aftermath.

12 Friends With: Paul Bearer

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After an initial stint of being managed by Brother Love, Paul Bearer was cast as The Undertaker’s manager. It was a near perfect pairing with a seasoned manager from Texas who’d actually worked with him prior to his Undertaker gimmick, not to mention that Bearer actually had real life experience as a mortician to make him feel altogether destined to stand in The Deadman’s corner.

Sure enough, The Undertaker and Paul Bearer would spend decades intertwined with one another. For years, Bearer was The Deadman’s manager through his first heel run, his first face turn, and when he turned back to the dark side. Then, when the two separated, it was for Bearer to play The Phenom’s chief antagonist, aligning with enemies like Mankind, Vader, and Kane in opposing him.

As the years went by, Bearer filtered in and out, just as The Undertaker himself transitioned toward part time status, and it’s telling that even in death, Bearer’s last angle would involve The Deadman avenging his old manager’s memory against a disrespectful CM Punk at WrestleMania XXIX.

The Undertaker and Bearer worked together so long not only out of on screen chemistry but because they were real life friends, often as not travel partners and confidants who were every bit as close as they ever appeared on TV.

11 Couldn’t Stand: CM Punk

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It’s about as traditional of a locker room beef as there could be, but The Undertaker had a problem with CM Punk as young upstart whom he viewed as not appropriately honoring the business.

The time was 2009 and CM Punk had gotten the better of a summer long rivalry with Jeff Hardy to emerge World Heavyweight Champion.

When Punk vanquished Hardy once and for all, Hardy was on his way out of WWE, and WWE needed to do something big to successfully transition the Punk and his title to their next story arc without losing the considerable momentum The Straight Edge Superstar’s heel turn had built up. The answer was to slot him in a rivalry with a returning Undertaker, who made a surprise return right after Punk beat Hardy in a TLC match at SummerSlam.

Punk and The Undertaker would feud for two months to follow, during which time The Phenom pointed out that Punk needed to present himself as more professional if he was going to carry around a world title and represent the company. While most WWE Superstars bowed to The Undertaker, Punk shrugged off the advice. The Deadman was upset with the disrespect, and it was widely rumored that’s why Punk wound up dropping the title shortly after.

While Punk seemed to have won over The Undertaker’s respect with their good matches at the time and years later at WrestleMania 29, one has to imagine that a WWE loyalist like The Undertaker also didn’t appreciate Punk walking out on the company, or publicly blasting it on the Art of Wrestling podcast months later.

10 Friends With: Vince McMahon

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The Undertaker may be Vince McMahon’s single most loyal employee. He’s worked with him for nearly three decades now, and that included the Monday Night War era when so many top talents defected to WCW, or expressed an interest in doing so. While the man beneath the Undertaker gimmick had worked with WCW previously, and Eric Bischoff has suggested that he had talks with him about coming back, The Undertaker remained loyal to the man who made him a star, and it’s telling that The Undertaker would not only main event four WrestleManias, but do so in three different decades of the events history (13, 24 and 26, 33).

The truth of the matter is that The Deadman and the Chairman have a tremendous level of mutual respect and even affection for one another.

The dynamic shone through via backstage footage from WrestleMania 30 that captured McMahon concerned for The Undertaker after he suffered a concussion at the hands of Brock Lesnar. McMahon was concerned enough, even, to leave the stadium to accompany his friend to the hospital.

McMahon is reportedly fiercely protective of The Undertaker gimmick and resistant to any ideas that might humanize or weaken him. In return, The Undertaker has reportedly extended his career and continued to make appearances less out of his own ambition than to help McMahon, knowing that his presence is still a money making draw with WWE fans.

9 Couldn’t Stand: Giant Gonzalez

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As mentioned earlier in this article, The Undertaker has been saddled with his share of less than desirable opponents, in no small part for to create big man versus big man match ups that felt like both believably competitive fights and epic collisions between larger than life men. Not all of these rivalries produced all that great matches, though, as exhibited by the 1993 issue between The Giant Gonzalez and The Deadman.

After playing affable giant El Gigante in WCW, Gonzalez signed with WWE where he was recast as a heel monster.

To cover up for his lack of muscle definition, WWE dressed him in a bodysuit with air brushed muscles (and fur). He debuted by attacking The Phenom at that year’s Royal Rumble before they went on to one of the most unimpressive matches of The Undertaker’s WrestleMania streak, which ended in a disqualification when Gonzalez attacked with a rag soaked in choroform. They went on to blow off their issue at SummerSlam.

Gonzalez was a prototypical physical marvel with no discernible talent for the wrestling business. Harvey Wippleman carried him on the mic as his manager. The Undertaker carried him to the extent he was able to succeed in the ring. The big man wasn’t particularly well liked and rode off into the sunset shortly thereafter.

8 Friends With: Steve Austin

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The Undertaker is that incredibly rare star who was featured before, during, and after the Attitude Era. Steve Austin certainly didn’t have The Dead Man’s length of tenure, particularly in WWE, but he was most certainly king during the Attitude Era as the most popular star WWE had to offer, the top merchandise mover, and a main event mainstay. As such, The Undertaker and Austin had their share of encounters in the ring from early in Austin’s time on top through the Two Man Power Trip and InVasion angles as WWE transitioned out of Attitude.

Through it all, Austin and The Undertaker developed a friendship with one another based on respect for their talents and the stories they could tell together (though Austin has lamented on his podcast that the two struggled with their actual in ring chemistry). More so than professional colleagues, though, they got to joking behind the scenes as Austin helped bring out The Phenom’s lighter side.

In one of the more famous cases of Austin and The Undertaker being buddies, Austin recounted their antics in his WWE produced documentary. The doc showed footage of an interview from the original Invasion PPV in which Vince McMahon rallied the WWE team, captained by Stone Cold. For each proclamation McMahon made, Austin parroted him to suck up, with increasing absurdity as The Undertaker rubbed his face. As was evident from Austin’s explanation, he was purposefully trying to crack up the Deadman and nearly succeeded.

7 Couldn’t Stand: Melina

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Wrestler’s Court is a device that was used to judge wrestlers when they seemed guilty of various infractions such as not observing wrestling etiquette or otherwise rubbing their colleagues the wrong way. As Edge and Christian recounted on their podcast, charges were brought up against them on account of their friendship with WWE writer Brian Gewirtz, with the allegation that they were kissing up to the creative team to better their position in the company. They also noted that the judge in these cases was notoriously easy to bribe for a light sentence.

The Undertaker was the de facto judge and presided over the trial of Melina. While Melina was an attractive woman and popular star among the fans for her era, she was not so well liked behind the scenes for her ego. More objective legends at the top of the business like Shawn Michaels, Steve Austin, or The Rock could get away with that kind of attitude because they had earned their position on top and, by the end of their full time careers, were generally well liked. As a valet and inexperienced wrestler, Melina was not in that league.

The details are sketchy about how Melina’s trial went, but multiple accounts indicate she left the closed door meeting in tears.

Far from a farce or a rib as Wrestler’s Court often turned out to be, she seemed to legitimately get dressed down by The Deadman, a clear sign he neither liked, nor respected her.

6 Friends With: Triple H

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While it’s well documented that The Undertaker didn’t always see eye to eye with The Kliq, if he were to get along wih any of them, it made sense that it would be Triple H. Like The Deadman, Helmsley was a serious, passionate student of the game who kept his nose clean, especially relative to his running buddies. Like The Undertaker, he also wound up being a star with staying power who stayed with WWE in a featured role longer than anyone could have guessed from the beginning.

Triple H demonstrated his respect for and friendship with The Phenom in actually seeking out his counsel as a younger man, when he began to develop feelings for Stephanie McMahon. The Game recounted the situation in the Thy Kingdom Come documentary, explaining what The Undertaker told him. If he were to pursue this relationship, everything he accomplished in wrestling would be judged with an asterisk and a different standard for the perception of the McMahon family favoring him. The main takeaway seemed to be that The Dead Man advised against it, but made sure Triple H knew what he was getting himself into.

Clearly things worked out for both men in their WWE tenures as they emerged icons, and worked together in the ring during different eras.

5 Couldn’t Stand: Diamond Dallas Page

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Diamond Dallas Page was one of the few bona fide superstars that WCW developed on its own, rather than signing after a successful run with WWE. He grew to remarkable popularity and became a world champion—all of this despite not actually getting started as a wrestler until his late thirties. When WWE bought out WCW, Page has admitted that he was unconcerned because he’d already been contacted by WWE management and knew he’d have a job waiting for him.

Upon debuting with WWE, there were a lot of possibilities for Page. For example, he had been billed as The People’s Champion in WCW, so might he feud with WWE’s wrestler who went by the same moniker, The Rock?

WWE could have done a lot worse than setting up a Page vs. Undertaker rivalry, but things went south quickly.

Page was booked not in his own big personality, but rather plugged into a more generic stalker gimmick to set up a feud with The American Badass. Things went from bad to worse as The Undertaker reportedly didn’t appreciate Page not knowing how to bump and feed in the WWE heel style, instead laying around and selling the WCW way, which was perceived as lazy.

Combine Page’s performance with The Undertaker’s predisposition to resent guys coming in from WCW, as the competition, and he was set up not to like DDP from the start.

4 Friends With: Ric Flair

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It’s interesting to note that Ric Flair’s interference was important in The Undertaker’s first ever world championship win at Survivor Series 1991. Over sixteen years later, Flair would wrestle his last WWE match at WrestleMania 24—the same show where The Undertaker wrestled (presumably) his last WrestleMania world title main event match.

In between these two milestones, The Undertaker and Flair worked with one another in the ring at WrestleMania X8. The Deadman was in a heel portion of his Biker gimmick, while Flair was playing a face authority figure. Though neither of these roles was what either man was known for, things gelled for this match with Flair playing the underdog to The Undertaker’s bully, and Arn Anderson making a fun run in on Flair’s behalf.

The WrestleMania encounter was important for Flair’s psyche. The Nature Boy has discussed his confidence having been shattered by the way WCW management treated him toward the end, and on account of his advancing age. The Undertaker expressed complete confidence in him and worked on a match set up for Flair’s success in a high profile situation. Flair credited his friend with putting him on a path to write a new final chapter to his career.

3 Couldn’t Stand: Brock Lesnar

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When Brock Lesnar first debuted on the WWE main roster, he was booked like a bulldozer, which included geting the best of a program with The Undertaker to further establish him The Next Big Thing as the new man in WWE.

But then Lesnar went away.

Lesnar left WWE ostensibly to pursue his dream of playing professional football, and would later find himself in a UFC Octagon.

From a variety of second hand accounts, these choices infuriated The Undertaker, who was already a legend by that time, and whose losses were valuable in strapping a rocket to whomever he put over. That Lesnar would squander this good will was the ultimate sign of disrespect to not only The Undertaker, but WWE and the wrestling business at large.

These tensions led to a fleeting confrontation between Lesnar and The Deadman at a UFC event where Lesnar had fought and the The Undertaker had attended as a fan, sparking speculation that The Beast Incarnate would return to WWE to face off with his old rival. It appears to have been unconnected, but Lesnar did ultimately return to WWE. While neither party has said much about it, they seem to have put their differences aside to make history with The Undertaker’s first WrestleMania loss in 2014, followed by a heated feud that headlined WWE programming in the summer and fall of 2015.

2 Friends With: Yokozuna

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Yokozuna was a dominant big man in WWE in the early 1990s. He was rarely beaten during that time period, won a Royal Rumble, and spent most of 1993 reigning as WWE Champion. Only top shelf stars were booked as legitimate threats to him, let alone booked to defeat him—guys like Hulk Hogan, Lex Luger, and Bret Hart. And then there was The Undertaker.

The Deadman and Yokozuna worked featured matches at the book end PPVs of 1994, battling over the world title at the Royal Rumble show, and then blowing off their issue in the main event of Survivor Series. In the first outing, The Undertaker was unique in posing a credible threat to the big man, and it’s telling that WWE booked a full cast of the heel locker room to help Yokozuna emerge victorious in their Casket Match. At Survivor Series, The Phenom got his win back with an assist from guest enforcer Chuck Norris, who kept at bay the heels who hoped to interfere.

The reality behind this year long on again, off again feud? The Undertaker and Yokozuna were both part of the Bone Street Krew that played dominoes backstage, traveled together, and watched each other’s backs. Their friendship was a testament to the old wrestling adage about the best on screen rivals often being guys who were the best friends behind the scenes.

1 Couldn’t Stand: Bob Orton

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For much of the year 2005, The Undertaker dedicated his efforts to helping get Randy Orton at the main event level. Orton had had a successful run as a young heel stud in Evolution, and particularly working the gimmick of the Legend Killer who’d take out veterans and visiting stars from yesteryear. These efforts pushed him all the way to beating Christ Benoit at SummerSlam to become the youngest world champion WWE had ever had. Sadly, Orton’s star fizzled from there, with an ill-advised face turn that demonstrated he was the kind of character fans loved to hate, and not yet equipped to actually play good guy.

Chasing The Undertaker’s WrestleMania undefeated streak offered a fine enough reason for Orton to turn heel, and after a rock solid match at WrestleMania 21, the rivalry would stretch forward.

Orton’s father, Cowboy Bob Orton, would become increasingly involved as his son’s sidekick, there to meddle and get in the Deadman’s way.

Everything came to a head at Armageddon 2005, where The Undertaker and Randy blew off their issue in a Hell in a Cell match. Everyone got bloody—the two participants in the match, naturally, but also Bob who interjected himself in the proceedings and who was as deserving of storyline vengeance as his son by that point.

Word has come out since that Bob had Hepatitis C. When The Undertaker became aware of this, after the two men had brawled with him, the both of them openly bleeding, he was reportedly furious for the unnecessary risk to his own health, and that Cowboy hadn’t been honest and up front about it. While Randy’s career would continue nicely, that was the last that was seen of his father in WWE.

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