The Undertaker is one of the most widely respected wrestlers of all time. He’s built a 25 year legacy with WWE as one of the company’s most iconic characters, a kayfabe top player, and evolving performer who has changed and improved with the times. Whether he was taking the WWE Championship off of Hulk Hogan at Survivor Series 1991, carrying big guys like The Giant Gonzalez and The Great Khali to passable matches, or putting on WrestleMania classics with Shawn Michaels, The Undertaker remains fundamentally important to WWE history. Moreover, he was a loyal company man who stood by WWE through the Monday Night War and ever since, like so few other talents.

The Undertaker is held in such high regard by his peers that he was appointed to the unofficial role of judge for wrestler’s court—a tribunal that evaluated wrestlers’ guilt for purported transgressions and assigned consequences. As silly as the custom may be, it the nonetheless demonstrated respect for him as a figure the boys trusted and whom no one would argue against.

Just because The Undertaker is well respected doesn’t mean there haven’t been people in the wrestling business who’ve crossed him. Whether they directly wronged The Deadman, had a slip in etiquette, or disrespected the traditions of the business, these are the individuals who drew The Undertaker’s ire. While, often as not, guys patched things up with The Phenom, this article recounts 15 figures in the professional wrestling business who pissed him off at one time or another.

15 15. CM Punk

By the time CM Punk rose to prominence, The Undertaker was already a well-established legend. Punk held the World Heavyweight Championship when a new edict was handed down about the WWE dress code, calling for guys to wear more professional attire. Punk bucked against the rule, citing previous champions who’d represented the company just fine while wearing jeans, and how John Cena himself didn’t abide by the rules, so why should he have to?

The Undertaker reportedly resented Punk’s gumption. He didn’t think Punk was in a place to question management, on top of which he felt he didn’t carry himself properly representing the company as a champion.

After getting off to a rocky start, by all accounts, Punk earned The Deadman’s respect when they started putting on matches together, first in series of matches in 2010, then at WrestleMania XXIX.

14 14. Buzz Sawyer

Buzz Sawyer was a reasonably successful wrestler, particularly in the 1980s. He worked for a time training wrestlers, but one of the least auspicious parts of his legacy came as an early trainer for the man who would become The Undertaker.

According to ring announcer Gary Michael Cappetta’s book, Bodyslams!, when The Undertaker showed up in WCW and found Buzz Sawyer worked there, too, he had every intention of killing him. The story goes that The Undertaker paid Sawyer all the money he had—the fee to train him how to wrestle. After a cursory lesson or two, Sawyer skipped town with all of the money his trainees had given him and The Deadman vowed revenge.

Cooler heads prevailed—Cappetta took credit for calming down The Phenom and getting him to look at the bigger picture of his career. Regardless, there’s no indication that Sawyer ever made amends.

13 13. Steve Austin

By all accounts, Steve Austin and The Undertaker got along and respected one another. But while The Deadman was committed to maintaining kayfabe at all costs, including maintaining his persona in public and in interviews long after it had gone out of vogue to do so, Austin could be a bit less straight laced. Austin was one of a few—and by many accounts the best—who tried to get The Undertaker to crack.

One of Austin’s biggest successes came in the build to the 10-man tag at the InVasion PPV. Austin, still a newly branded heel, played a kiss-up to Vince McMahon, and humorously riled up his teammates by echoing everything McMahon said in increasingly obnoxious fashion. Throughout the segment, The Undertaker could be seen, over and over again rubbing his hand over his face to obscure his smile and to cut himself off from breaking his badass character by laughing out loud.

No doubt, the ribbing pissed off The Phenom for undermining his professional style. He and Austin quickly put it behind them and continued to coexist nicely on the WWE landscape for years to come.

12 12. Mabel

Injuries happen in professional wrestling, and even most skilled, careful performers are responsible for accidentally hurting at least a few of their colleagues of the course of their careers. In 1995, however, Mabel earned a reputation for being dangerous. The five-hundred-pounder was blamed for a number of injuries, most notably one to Kevin Nash which, while less serious, Nash has claimed nearly cost Mabel his job.

After the feud with Nash, Mabel was set up against The Undertaker but delivered a leg drop that legitimately fractured The Deadman’s orbital bone. The injury put The Undertaker out of action for a period of months. The Undertaker had previously feuded with men of similar size like Yokozuna and Kamala, with big men who had little coordination like The Giant Gonzalez, and even with a monster who was known to be accident-prone in Sid. After surviving each of these programs unscathed, The Undertaker had to be upset at enduring this painful injury at the hands of guy who already had a bad reputation, and who you’d think would be all the more careful because of it.

11 11. Vince McMahon

When two people work together for as long as The Undertaker and Vince McMahon have, and particularly in as stressful an environment as WWE, it’s to be expected they’ll have some run ins. While there have been a number of reported dust ups between these two over the years, none compared to the aftermath of The Montreal Screwjob.

The Undertaker was purportedly furious when Bret Hart was deceived and discarded on his way out of the company. By several accounts he immediately confronted McMahon about what had happened backstage, and demanded that McMahon apologize to The Hitman (though, other accounts have McMahon doing so of his own volition). Some rumors suggest The Deadman was also among those stars who considered quitting over the incident, though cooler heads prevailed in that regard and he continued with the company.

10 10. Shawn Michaels

In the build to WrestleMania XIV, Shawn Michaels’s back was badly injured. A plan was set in motion for him to lose the world title to Steve Austin, who was quickly becoming the biggest star in WWE anyway. However, as the day neared, Michaels purportedly expressed his doubts about whether he should actually drop the title.

Accounts vary as to whether The Undertaker actually confronted Shawn Michaels, or merely talked about doing so if Michaels wouldn’t do business. Regardless, the consensus was that The Phenom didn’t like how Michaels carried himself at that point in his career, and was prepared to get in his face if he didn’t actually do the right thing at WrestleMania.

Ironically, years later Michaels and The Undertaker would have great respect for each other, collaborate beautifully for a match at WrestleMania 25, and then mutually campaign for the main event rematch one year later.

9 9. Diamond Dallas Page

There are a lot of rumors as to why Diamond Dallas Page’s WWE run was such a flop, and particularly why The Undertaker dominated him so thoroughly in their feud. The part that just about all sources agree on: The Undertaker did not like Page. As a well respected veteran, he was, thus, able to conduct the program as he saw fit.

One of the prevailing theories as to why The Undertaker had a beef with Page was that he resented WCW guys in general when they came to WWE. He purportedly still saw them as the competition, and resented it even more when they took jobs and high profile spots from loyal WWE guys. Though The Undertaker hasn’t spoken on record about it, Page supported this point of view in an interview with YouShoot. Other rumors cite that The Undertaker was reportedly frustrated with Page’s working style—that rather than bumping and feeding in the style of WWE, he would like on the mat and sell every time The Undertaker took him down, much to The Phenom’s annoyance.

8 8. Matt Hardy

At the end of Survivor Series 2005, The Undertaker made a surprise return to confront Randy Orton, who had previously put him out of action. The Undertaker stormed the ring and took out a bevy of stars to get at Orton. Allegedly, Matt Hardy was specifically earmarked to take a choke slam during the onslaught.

According to The Wrestling Observer and a variety of other sources at the time, Hardy didn’t think that taking that bump from The Undertaker would fit his character at the time, and thus quietly slipped out of the ring. The Undertaker purportedly confronted Hardy about it backstage, giving him a stiff scolding in front of the rest of the roster. In particular The Deadman accused Hardy of thinking he was better than the rest of his colleagues.

7 7. The Big Show

Early in The Big Show’s WWE tenure, he worked an angle in which he played tag team partner and protégé to The Undertaker. Little did fans know that life imitated art at this stage. The Big Show was still green and didn’t get the best mentoring during his early work with WCW, so The Deadman took him on as project. The way Big Show has described the mentorship, it involved a lot of The Undertaker ripping into him backstage, furious at everything Show still got wrong.

Through the apprenticeship, the two developed a friendship and strong mutual respect. It’s little surprise, then, that WWE has revisited the rivalry a number of times over the last two decades so the big men have gotten more opportunities to work together.

6 6. Brock Lesnar

In 2004, Brock Lesnar left WWE to pursue football and, when that didn’t work out, a more successful career in mixed martial arts. Lesnar had only had two years on the main roster, during which time he received one of the biggest pushes in wrestling history, not least of all decisively defeating The Undertaker.

The Undertaker isn’t known for refusing to job, but he is known for being protective of his character and wanting to make sure his losses count for something. This was especially true by the time Lesnar first surfaced in WWE, given The Deadman was a well-established main eventer and former world champion by that time. For Lesnar to cleanly defeat The Phenom, only to up and leave WWE a couple years later came across as a slap in the face. The tensions seemed to carry over to a brief standoff between the two at a UFC event while Lesnar was fighting, before he returned to the WWE fold. There’s been a lot of speculation about whether the moment was a work or an incidental bit of contact that fans blew out of proportion. Regardless, it wouldn’t surprise anyone in the wrestling business if The Undertaker had still held it against Lesnar that he walked away from the business.

5 5. Vince Russo

Vince Russo was a big contributor to WWE’s creative team who especially influential during the early stages of the Attitude Era. Russo left WWE and signed with WWE, at which point he became more of a household name as not only a behind-the-scenes player, but an on-screen authority figure.

Russo apparently did not know that he had heat with The Undertaker until years after he’d left WWE. It then came to his attention that his creative had gotten The Phenom pretty riled up. The issue is that The Undertaker took some well-earned time off of wrestling to recover from injuries, but remained an on-screen character in the interim. Russo claims that he must have underestimated The Deadman’s injuries, as he still wrote segments which involved The Undertaker getting physical and taking punishment in the ring during this time, despite not wrestling.

4 4. Mo

While the details vary, it seems that Mo from Men on a Mission had a chip on his shoulder going into the 1996 Royal Rumble. The story goes that he and his real-life friend and on-screen partner Mabel felt disrespected. Tensions boiled over when Mabel splashed and injured Henry O. Godwinn. It wasn’t clear if the spot were an accident, or if the team had intended to send a message.

The Undertaker, emerging by that time as the law and order of the locker room, was understandably pissed at them. He purportedly confronted both of them backstage and promptly tore into them. In an interview with In Your Head Wrestling Radio, Mo said that he thought Mabel and The Undertaker would legitimately become to blows in that moment, and that he was upset, too, but cooler heads ultimately prevailed.

3 3. The Pyro Technicians at Elimination Chamber 2010

The Elimination Chamber Match for the World Heavyweight Championship in 2010 saw a bizarre beginning when reigning champ, The Undertaker made his entrance only for his flaming entrance pyro to malfunction. His jacket caught fire. Fortunately, he reacted quickly enough to get the jacket off and avoid a more serious injury, but he did reportedly receive first and second degree burns.

The referee handed The Undertaker multiple bottles of water to pour over his arm from his chamber as he awaited entry into the match. The Dead Man was understandably livid at the pyro technicians after the match. Chris Jericho, who won the match, has spoken in numerous interviews about the individual responsible for the accident being fired promptly—and that this outcome was probably far better for him than if The Undertaker had gotten his hands on him.

2 2. Bob Orton

Randy Orton and his father Bob feuded with The Undertaker during the period after The Attitude Era, but before WWE leaned fully into what’s popularly known as the PG era. Consequently, the feud still featured all three performers getting bloodied on more than occasion.

Little did The Undertaker know, Bob had Hepatitis C. When The Undertaker found out afterward, he was purportedly livid at both Bob and John Laurinaitis, a backstage power broker who purportedly called for Bob to get color, even though he knew that he’d tested positive for Hep C. The Undertaker had unknowingly put himself at serious risk of having the disease transmitted to him. Luckily, he wound up being okay, but that did little assuage his justifiable anger. Bob left the company soon after.

1 1. Chris Jericho

Chris Jericho recounts in his book Undisputed how rough of a time he had early in his WWE tenure. This included delivering promos that guys took the wrong way. Most notably, he called The Undertaker boring without clearing it with The Deadman in advance.

While one could easily surmise that Jericho was speaking in character and didn’t mean any offense, The Undertaker was purportedly pissed, as were a number of other guys with political clout. That included Shawn Michaels, who Jericho wrote smartened him up about the mistake as soon as he got backstage. While The Undertaker and Jericho would go on to work together successfully down the road, one has to suspect that this misstep set him off on the wrong foot, and may explain Jericho’s struggles to, despite a hot debut, get a real push for his first few years with the company.