Pull back the curtain on the often veiled, highly respected, longest-tenured WWE wrestler of all time- the phenom himself, the Undertaker! As these eighteen stories show, not only was he the stuff of legend in the business, but he was behind the scenes as well!
1. Sgt. Slaughter on Discovering The Undertaker
In an interview with the Baltimore Sun, Sgt. Slaughter shared the story of how he discovered Mark Calaway, the man who would soon become The Undertaker.
"When I was working in the [WWF] office up in Connecticut, part of my job was to go through the boxes of letters and resumes. One of them happened to be a young kid by the name of Mark Calaway, who has short red hair, and he was working down in WCW.
"It was a tape and a little letter saying he’d be interested.
"At the time, he was in a tag team. I remember on a Saturday I went to Vince McMahon’s office, and I said I got this guy you should give a tryout to, and Vince said he trusted me.
"WWE brought him into Rochester, NY. I showed Mark where to go. I said, ‘You’ll be the first match on the show.’
"Halfway through the match, I was on the headset, and I hear Vince McMahon say, ‘Where did you find this guy? Send him to my office.’
"Mark came out of the ring and asked me how he did, and I said Vince wanted to see him.
"He thought he did something wrong.
"We would have meetings after shows to talk about what happened and plan things out creatively. The topic turned to Mark, and Vince said he had an idea for a character name, and he brought up the name ‘Paul Bearer.’
"The next day I went to Vince, and I said I didn’t really care for that name for Mark in particular; I thought he looked different than that, and Vince said, ‘Like an Undertaker?’ and I said, ‘Yeah! Maybe we should do Paul Bearer as his manager…’"
2. Bret Hart on His First and Last In-Ring Encounter with The Undertaker
In his recommended autobiography, Hitman: My Real Life in the Cartoon World of Wrestling, Bret Hart opened up about the Undertaker.
"It was bizarre to meet Vince’s new gimmick: a towering red-haired kid from Houston named Mark Calaway, his Huck Finn features hidden by the dark circles painted under his eyes to give him the look of a cadaver. He was The Undertaker, dressed all in black, complete with a wide-brimmed hat. Pat explained to all of us that Vince wanted him over super-strong didn’t want him even leaving his feet.
"How odd that, today of all days, my job was to battle death in a strange kind of morality play.
"Once The Undertaker was eliminated by disqualification, I was to be the last man standing against The Million Dollar Man.
"As fate would have it, I was the first WWF wrestler to ever lock up with The Undertaker. Little did I know that, much farther down the road, he would wind up being the last wrestler to work with me in the WWF."
3. Jake "The Snake" Roberts on Taking Undertaker Under His Wing
In a 2012 interview with Busted Open with Doug Mortman and Dave LeGreca, Jake Roberts shared an early Undertaker story.
"I was there when he first got in there in the WWE.
"He comes to me and says, ‘Hey, I hear you know where all the good strip joints are at…’
"And I’m like, ‘In the world? Yes. I know them all.’
"And he’s like, ‘Well, I’ll travel with you!’
"I said, ‘Oh boy, why don’t you go back to playin’ basketball because you’re not gonna be able to hang with me… I’ll kill ya…’
"And a few weeks later, he was in pretty bad shape with alcohol poisoning. (Laughs)
"Yeah, but it was a ‘chemical’ world, so I was cheating, man. He didn’t know it. I wasn’t gonna tell him!
"He rolled with me for quite a while. We’re great friends, and I’d like to think that I helped him more. I think if you asked him, he’d tell you that he learned a lot from me. I love the guy."
WhatCulture added to the story:
"Jake Roberts describes his first-ever meeting with Mark Calaway as one that centered around strip clubs and alcohol consumption.
"‘I love your work, but I hear you know the greatest strip clubs in the world, and I want to ride with you,’ Taker apparently said to Jake.
"The grizzled and heavy drinking Snake didn’t believe Taker would last a week traveling with him but took him under his wing anyway. Just a week later, Taker was having his stomach pumped in the afternoon and wrestling in the evening as if nothing had ever happened. According to Jake, it was as if Calaway didn’t even need to wear the Undertaker make-up anymore, given how whited out his face was from drinking.
"In some ways, this was pretty normal behavior for a wrestler in the industry back then. Large amounts of alcoholism were just a way to bond with ‘the boys’ and strippers were the cool thing to do back then on the road."
4. The Ultimate Warrior on The Undertaker
In his 2008 interview with Ringside Collectibles, Ultimate Warrior shared his thoughts on the Undertaker.
"I liked Mark. He was a good guy.
"They brought him in and kept him off the TV [at first], thinking about what character to give him.
"The people really got behind The Undertaker gimmick. It was creatively stimulating. I liked it, man.
"Mark is certainly one of those deserving great respect for what he’s accomplished in the business.
"I was the first guy to work with him. Even though Ultimate Warrior was over as a huge babyface, the ticket buyers dug his gimmick. I could have, with the position I had, been an a-hole and worked in unknown ways to curb that.
"Too many guys in the business spend too much time conniving ways to make someone else look worse, rather than spending that time on becoming better themselves.
"Instead of trying to damage his gimmick, though, as many in the business would have done, I embraced it and worked with him to get it over as the people wanted to have it over.
"He was going to be a great talent, and I was inspired by that. It made me want to better my own.
"When I got shut in the coffin, a lot of people were aghast. They’d say, ‘God, you’re gonna get in the coffin…and they’re gonna close it!’
"Like it’s almost blasphemous or something.
"It wasn’t my idea, but I wasn’t against it. Actually, I joked, I said it was the most rest I’d had in a long time!"
Watch the 1991 ‘Body Bag Match’ Between Ultimate Warrior and The Undertaker:
5. Randy Savage Talks about Wrestlers’ Court with The Undertaker as the Judge
In an interview with IGN, Randy Savage opened up about Wrestlers’ Court with Undertaker at the helm.
"Back in the locker room, there was a code – a ‘wrestler court.’ Vince McMahon used to honor it.
"It was a moment in time where if you were out of line in the dressing room or something like that, you might be called out right in front of everybody to tell your side of the story.
"Its entertainment value was way off the charts.
"The Undertaker was the judge. One of the prosecuting attorneys was Brian Adams.
"It doesn’t go on like it used to, but I heard it almost kicked back in. It’s just that Undertaker wasn’t there to do it. But I miss that part of it.
"I was never really called before the court; I was always in the audience. I think I got away with a lot of shit because people respected me for being ‘old school’ or whatever. Plus, I knew Master Fuji on a first-name basis, and he was the king of the ribs. He could give protection. (laughs)
"I’ll just say that there are a lot of ribs in wrestling, and there are a lot of patient fishermen. You might get your sentence right there, but it might be the first of a long deal. You don’t want to make the boys mad at you, but at the same time, you need to stand up for your rights. And the boys will listen. The boys are great. If you treat the boys right, you respect them; the boys will run through walls for you.
"Wrestling is a fraternity, and the boys will work their butts off for you as long as you respect them and don’t lie. You can’t walk all over anyone, or everybody will walk all over you.
"Here’s the deal, there are no tough guys in wrestling. If you come in and act like you’re a tough guy, you’re in trouble the second you walk through that dressing room…"
You can read all about Wrestlers’ Court here!
6. The Undertaker and His Fear of Cucumbers
The story goes that Taker always used to travel with Paul Bearer because it helped protect his gimmick. Being an old school kind of guy, Taker always protected kayfabe and insisted on not being pictured out of character. As such, whenever Bearer and Taker traveled together, the manager was always the unlucky one who had to get out and fill the petrol.
One day when they stopped to fill up, Bearer was desperate to use the bathroom. Undertaker showed no mercy and made his manager fill the tank first, which resulted in Bearer wetting his trousers. Undertaker found this hilarious and quickly spread the story to Vince McMahon and the locker room.
How did Bearer get his revenge? Aware of Undertaker’s bizarre phobia of cucumbers, he proceeded to fill The Deadman’s hat with the vegetable, topping it up with the green right to the brim. When Taker picked the hat up and caught sight of the cucumbers, he legitimately freaked out and gagged.
Paul Bearer Opens Up About Undertaker’s Fear of Cucumbers:
7. Kevin Nash on The Undertaker’s Love of Jack Daniel’s
The Undertaker’s drink of choice is Jack Daniel’s whiskey, according to Kevin Nash, who described it as a ‘love’ for the drink.
Whether Taker still drinks to a large degree is unlikely. In the 2003 ‘WWE Unscripted’ book, he remarked that his ex-wife Sara showed him happiness without the need for a drink.
Before Undertaker cleaned up his act, he was a hellraiser of a drinker, according to Nash. Undertaker was known for being a party animal and would regularly take a limo with Nash and Charles Wright to get drunk and cruise the local strip clubs in New York or Las Vegas. These drinking sessions would last all night!
8. Association with Jenna Jameson
In her autobiography, How to Make Love Like a P*** Star, Jenna Jameson revealed that The Undertaker hung around with her when he was on the road in Las Vegas.
Jameson was only 16 at the time and would watch on with shyness as the wrestling star visited the tattoo parlor she worked at. Supposedly they ended up hanging out and became good friends.
Jameson proved to be the perfect gullible mark for kayfabe. "Undertaker was one of the biggest WWF wrestlers at the time. He would put people in coffins and set them on fire in the ring. And the scary thing is, that character he played was not an act," she detailed in her book.
Later on, she talks about a time he came to one of her shows and chased off a guy who was trying to buy her a drink, "You can get me a shot of Jaeger, and you can get yourself a shot of shut-the-fuck-up," he apparently barked at Jameson’s suitor.
The Deadman then tried to woo Jenna, telling her, "I’m going to kick your boyfriend’s ass and take you away with me."
She recalls, "I knew he was serious. I ran upstairs and told Jordan we had to leave because this guy was going to beat the fuck out of him and kidnap me. So I never saw him again."
9. Breaking the Rules By Going to Strip Clubs
One thing that’s strikingly obvious in old stories about Undertaker is how much he enjoyed boozing and strippers. In an interview with Joe Dombrowski, Kevin Nash shared how Undertaker betrayed Vince McMahon on a strip club rule.
Basically, there had been some sort of problem where Vince banned his crew from strip clubs due to an altercation there had been. It was seen as a negative to the family company image, so the Chairman basically barred everyone from going. Kevin Nash loved strippers, so he decided ‘screw it’ and just went anyway.
Trying to keep a low profile, Nash entered a strip club and looked for a dark corner, but who does he see as he’s looking around? A big man in a motorcycle jacket is looking shiftily back at him. That’s right, The Undertaker was one step ahead of Nash and had already gone ahead and broke Vince’s rule.
"I see you listened," they both said to each other.
10. Justin Credible on Doing LSD with The Undertaker
In an interview with No-Kayfaben, Justin Credible recounted that his first ever experience of acid was with The Undertaker on a flight to Europe.
According to Credible, once he started ‘tripping,’ he was freaked out by The Undertaker, who was making cat movements and hissing at him.
Another version of this event says that Undertaker stuck his tongue out and rolled his eyes back to intimidate Justin. In his hallucinating state, Credible says he almost had a heart attack as he beheld Undertaker’s devil-like appearance.
This is quite a funny story in that it shows Taker was down in the trenches with the lower talent and was laid-back enough to have some fun. It also shows that there was quite the WWF’s drug culture at this time, to a point where dropping acid was a trivial game between two wrestlers. That was the wrestling world back then. Credible’s shoot interview wasn’t admonishing Taker for what happened; it praised him for being ‘one of the boys.’
11. The Rock Shares a Feel-Good Undertaker Story
In his book, The Rock Says, Dwayne “The Rock” Johnson shares how Undertaker helped propel him into superstardom.
"There was a very specific incident that demonstrated to me exactly what kind of a man the Undertaker is.
"It was while I was teetering on the upper edge of the second tier, getting ready to leap to the top tier. The Rock was on the border of super-stardom, within a breath of reaching a level of success that only a handful of wrestlers attain.
"The Undertaker, of course, was already there, and he was my opponent on this particular edition of Raw.
"We were in Detroit, at Cobo Arena, and the decision had been made that I was going to win the match. So, in essence, my fate was in the hands of the Undertaker.
"He had the opportunity, all by himself, to propel me to the next level, to reach down and pull me up alongside him. He also had the power to make me look mediocre.
"The Undertaker would never deliberately go out and make someone look like complete shit because he’s too much of a consummate professional. He’s too smart a businessman to do something like that, which is one reason he’s been so successful.
"But he did have other options.
"He could easily have said, ‘Have The Rock beat me via disqualification.’ He could have said, ‘Have The Rock hit me with a chair, knock me out cold.’ That way, everyone would have said, ‘The Rock had to use a chair to beat the Undertaker.’ It was entirely up to him. All that had been determined was the outcome: The Rock would win, the Undertaker would lose. How we would arrive at that point was up to the Undertaker.
"His decision was to put me over clean – one-two-three! – in the middle of the ring. Not only that, but he decided it would be best if the Undertaker was beaten by The Rock’s signature move, The Rock Bottom. That would ensure maximum exposure for The Rock and maximum entertainment for the crowd. It made me realize what a true professional this guy is.
"I will never forget meeting the Undertaker before the match and saying, ‘Man, I just heard it’s going to be a clean finish. Are you comfortable with that? Are you sure you want to do that?’
"He looked at me and said, without hesitation, ‘Absolutely. It’s your turn, and it’s your time.’
"Having grown up in the business, and having seen business conducted that way…and not conducted that way…I couldn’t help but be moved by such an impressive gesture. It really wasn’t possible for me to thank him enough, but I tried anyway.
"‘Somewhere down the road I’ll have the opportunity to do the same for you,’ I said. ‘And I want you to know…I’ll do it in a heartbeat.’"
12. The Time Undertaker Choked Out Kurt Angle for Real
Kurt Angle recounts an Undertaker story in his WWE autobiography, ‘It’s True! It’s True!’
Angle had been playing around for weeks with Vince McMahon in a game where they would take the other man down by surprise. Much to the Chairman’s delight, he had actually managed to score a takedown over Kurt and wouldn’t let it go – he reminded Angle of it on every occasion he could.
It was all good-natured, but the Olympic gold medallist wanted revenge, so he started to plot a surprise’ play attack’ on the boss. The time to execute his own takedown came during a plane ride to Europe. Spotting the boss unaware, Kurt pounced on Vince like a cat; little did he know the can of worms he had opened. The Chairman spent the rest of the plane ride waiting to jump Kurt back and eventually did in a takedown that spilled out into the aisle as a fun play fight.
One man who had been unaware of all of this was The Undertaker, who was literally a sleeping giant. The scuffle continued, and Taker was awoken by the commotion, reacting with shock to what he thought was his boss getting beat up. He reacted the only way he naturally would – jumping on Kurt and applying a chokehold, which was seconds away from putting the star to sleep!
Luckily Vince explained the situation before Angle’s lights went out, and they all had a good laugh about it.
13. Chris Jericho on Kissing The Undertaker
In his second autobiography entitled Undisputed, Chris Jericho shared a humorous story about the Undertaker:
"Because we were taping both shows in Tokyo, it was a rare tour that boasted both the Raw and Smackdown! rosters.
"The whole crew had gone out to Roppongi the night before and gotten totally shmammered.
"I don’t remember much about the whole evening, except for the fact that I spent a good portion of it trying to convince The Undertaker to let me kiss him on the lips. There was no way the Fonz was going to allow that to happen, but he did let me kiss him on the cheek, so it wasn’t a total wash."
14. Chris Jericho on the One Man with the Power to Combat the nWo: The Undertaker!
The following Undertaker story by Chris Jericho also comes from his book, Undisputed:
"There were quite a few members of the roster who remembered what it was like in WCW when the NWO was in power, and they weren’t thrilled about their impending arrival. The whole locker room was up in arms, uncertain as to what exactly would happen when they arrived. Would they destroy the locker room with their horrible attitudes? Would they work their dark Jedi mind tricks on Vince like they had Eric? Who could stop them? Who would save us?
"There was only one man with the power to combat the NWO. I had to seek out the man who had everybody’s respect across the board and the greatest influence within the company. He was the oracle. He was the swami. He was the Fonz. He was the Deadman.
"I expressed my concerns to The Undertaker, who listened intently before giving me his thoughts:
"’The one thing that’s different here is that Vince is the boss. He’s in charge, and we all know it. In WCW, there were half a dozen bosses, which made it easy for everyone to get what they wanted. These guys are going to do business and do what they’re told, and if they don’t, they won’t last. I’ll make sure of it.’
"With that, he waved his hand and disappeared in a cloud of smoke.
"The master had spoken.
"All shall be well, and all manner of things shall be well."
15. The Undertaker and his BSK (Bone Street Krew) Tattoo
One of Undertaker’s most distinctive tattoo’s is the BSK Pride one across his abdomen.
It was actually a drunken etching Taker got done one night when hanging out with other wrestlers and joking about forming an alternative backstage group to Shawn Michaels’s Kliq. The ‘Bone Street Krew’ was born, consisting of Taker, Yokozuna, Charles Wright, and others. This has been confirmed in shoot interviews from Nash, X-Pac, and Paul Bearer.
The group was more a bit of fun and camaraderie compared to the real power of the Kliq. Undertaker was actually good friends with Kevin Nash, so it wasn’t like he was trying to rival the Kliq or take a dig at them. This was just a fun way to send a message to the Kliq that other things were going on backstage in the WWF.
The decision to get the drunken tattoo might be one Taker regretted given that the group had no real, lasting infamy, but still, it looks pretty badass to this day.
16. Taping Up His Fists and Threatening Shawn Michaels
What, did you think you’ve gone this far, thinking I forgot to include the most legendary backstage Undertaker story of all? Come on now!
The most legendary backstage story about Undertaker will always be the occasion he taped his fists up and threatened violence against Shawn Michaels.
Taker did this because he had got sick and tired of seeing Shawn mess around with WWF business. The Heartbreak Kid had pulled out of a planned loss to Bret Hart at WrestleMania 13 due to an injury (which some believe he faked); he later went on to ‘screw’ Bret Hart at Survivor Series 1997 in what was a shock to the entire locker room. By conspiring with Vince to change a result without his opposition knowing, Michaels had betrayed the entire locker room – Undertaker was legitimately furious.
When it came to WrestleMania 14, it was the turn of Steve Austin to get a run with the WWF title. Austin was the hottest thing going and a genuine shot for the WWF to become a financial success again. Would Michaels do the right thing and put the star over? Undertaker, as a locker room leader, was taking no chances. He got in Michaels’ face and showed his fists, letting the egotistical star know that if he did anything other than putting Austin over, he would face the consequences.
The result went off without a hitch: Michaels lost to Austin clean, and the most successful era in the business was started.
Meanwhile, Undertaker unwrapped his wrists and carried on with his business as normal.
Shawn Michaels would give his take on this in an interview with Sports Illustrated.
"Back then, Mark didn’t like me," Shawn admitted, "but at no time has he ever claimed that he said anything to the face of Shawn Michaels, and that’s because he didn’t. Mark went to everybody and told them, ‘If this doesn’t go down the way it should, I’m going to have a big problem, and Shawn is going to have a big problem. I’ll go over there and beat the heck out of him.’ But he never had to say anything to me.
"My whole intention at WrestleMania XIV was to drop the belt to Steve, but I was going to make everybody sweat it out and make them think I wasn’t. Obviously, I got that accomplished. That’s extremely unprofessional, but that’s exactly who I was and what I was doing."
17. Ric Flair on His Admiration for The Undertaker
In his WWE Hall of Fame acceptance speech, Ric Flair shared stories of respect and adoration towards the Undertaker.
Ric Flair said, "One of my best experiences in WWE has been the opportunity to work with The Undertaker. I’ll never forget him asking me to work with him at WrestleMania 18. I would have to say the honor was all mine.
"There will never be another character like Taker…and he is as responsible as anyone for the company’s tremendous success.
"When I wrestled him in Toronto, I hadn’t been in the ring much [at that time], and this is how cool he is…he knew I wanted to do the flip [over the turnbuckle] and he was going to give me a kick off the apron…but I missed it.
"He walked back around the ring in character, picked me up, put me in the corner, and he said, ‘Kid…can you make it this time?’ (Laughs) I said, ‘I’ll try!’ This time we nailed it.
"I’ll never forget walking back through the curtain after that match, and Jack Lanza said to me, ‘You old sonnova bitch…you can still go!’"
18. The Undertaker on Why He Wouldn’t Retire
In an interview with the Houston Chronicle, the Undertaker discussed why he wasn’t quite ready to hang up his boots.
"Honestly, I love it, that’s why.
"I’ve got [all these years] in the business and all these injuries, but WrestleMania has become so huge, it’s just hard to walk away from it. I want the audience leaving the stadium going, ‘Wow!’ It’s a responsibility I have being a top dog in this business. The crowd will let me know when it’s time to leave. They haven’t yet.
"And if I didn’t perform at WrestleMania, in some strange, weird way, I’d feel like I was letting Vince McMahon down. I’ve been in the WWE for so long, and he’s done so much for me.
"[Away from the ring] I spend a lot of time with my family, my children. I also work on my horrible golf game. I love golf, but I’m awful. For some reason, I go out there and make myself miserable because I’m so bad at it.
"But most of my time is spent healing up … so I can be the Undertaker again.
Undertaker mirrored those thoughts in an earlier interview with The Score.
"My biggest worry in life, as far as wrestling is concerned, is that I’m in the ring and some father who watched me for years takes his son, and he goes, ‘You know son, this is The Undertaker here; wow, I wish you could have seen him when…’
"That means it’s time for me to hang it up.
"Hopefully, the guys that I work with, they would tell me, ‘You know what, Take’? You might need to think about something…’ You know? Because I would hate to know that anybody ever [held] back to protect me. Because that’s not what I’m about. I’ve made my money, and I’ve done well and all that. Why I wrestle now is because I enjoy this.
"As long as I can go out and I can hang with our top guys, I got no reason to leave."
During the final episode of Undertaker’s "The Last Ride" documentary on the WWE Network that aired on June 21, 2020, the Undertaker hinted at his retirement, saying he had nothing left to prove after 30 years in wrestling and had no desire to step in the ring again. He, however, did not rule out the possibility of returning in the future.
If you enjoyed this piece, be sure not to miss the following articles on our site:
- Meet The Man Who Trained the Undertaker – “The Spoiler” Don Jardine
- The Undertaker’s First Year in WWE: Rise of The Dead Man
- Ric Flair | 13 Stories Showing Who the Real Nature Boy Was
Some quotes used in this article compiled by Matt Pender and shared here with thanks to our friends over at ‘Wrestling’s Glory Days’ Facebook page.
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