Mark Calaway, aka The Undertaker, has been a permanent fixture of the wrestling industry for what seems like forever. He made his foray into the world of wrestling entertainment probably before most of you were even born, and quickly went on to build a name for himself and establish himself as one of the best of all time. That whole Deadman gimmick is certainly one of the greatest, and Calaway’s persona, the way he’s lived up to it for decades, and hasn’t flinched from it, has been truly remarkable.
The Undertaker is a name that’s synonymous with WWE, having been contracted with the promotion since 1990. It’s just amazing to think that he’s been around for so long, and how much he’s actually managed to achieve during this time. He’s had high moments, and there have been lows too, but he’s certainly cemented himself as a legend of the ring.
Even though everyone knew it was coming, that his retirement was imminent, fans were distraught when The Undertaker stepped into the ring for the final time at WrestleMania 33 on April 2nd of this year. He left that famous attire in the ring before slowly making an exit to the sound of his chilling music, kissed his wife, then descended down the ramp. It’s safe to say that there were probably quite a few tears spilled that night.
Here are 15 interesting facts you probably didn’t know about the recently-retired Undertaker; 15 things about the sheer legend of wrestling that is the Deadman, the Phenom, The Undertaker.
15. Third Time’s A Charm
Wrestling’s a pretty hard industry in which to find true love, to form and develop a stable family life. Life with the top promotions means living out of a suitcase, being on the road for the majority of the year, and spending more time in hotels than your home, so establishing a decent relationship can be pretty tricky. Calaway has certainly found it to be so anyway. He hasn’t had the best of luck when it comes to marriage. His first marriage was in 1989, when he was still a rookie in the wrestling industry. The marriage lasted for a decade before they went their separate ways, and then a year after the divorce was finalized, he moved onto his second wife, Sara. She was actually involved in the wrestling industry, for a little bit anyway, but their romance eventually fizzled out, and Calaway went on to wed one of the best divas in the industry at the time, Michelle McCool. Seven years later and they’re still going strong, and have a daughter to complete their family.
14. He Is A Real Estate Investor
Most wrestlers have a side venture or two to keep the money coming in, to have something they can turn to once the curtain closes on their wrestling careers, and The Undertaker’s no different. But having said that, it’s safe to say that not a lot of people would’ve expected him to be a pretty high flying real estate investor.
Calaway’s been investing in real estate for decades now. He makes investments with his business partner, Scott Everhart, and together they either construct, buy, or do up properties across America. One of his biggest projects is the $2.7m building in Loveland, Colorado, called “The Calahart,” which the two constructed from scratch. Investing in real estate is far from just being a hobby for Calaway. It’s a legitimate business that he’s heavily involved in, he’s made shrewd investments over the years, and they’ve paid off, making him a ton of cash in the process.
13. History With Jenna Jameson
Calaway’s hung out with some pretty badass, weird, and wonderful people during his time in the limelight, and even before he became the legend that he is today. He had a posse, and someone who he spent a lot of time with was Jenna Jameson. Jenna Jameson, for those of you who don’t know, was once regarded to be the queen of porn, and Calaway was pretty tight with her during his younger days, before he became a Deadman, relatively speaking. They used to hang out in tattoo studios and that’s where they met, got talking, and struck up a friendship. But Jenna recalls in her book, that Calaway was one seriously weird dude, even back then. He was just so intense, so serious, and she even describes him as being psychotic. Needless to say, their friendship didn’t last; the last time she saw him was when he threatened to beat up her boyfriend and kidnap her – one crazy dude, if all’s true of course.
12. Hollywood Comes Calling
Most wrestlers, especially bigtime wrestlers who have a massive fan following, have tried their hands at acting in movies. Actually, even if you’re a half decent wrestler, there are plenty of opportunities out there for you to get stuck into Hollywood. WWE have their own film production company, releases its own movies, and if you get noticed in these, you could very easily move on to bigger and better things.
The Rock and John Cena and a couple other prominent wrestlers have done the whole movie thing and have done more than a bit well at it, I’m sure you’d agree. But Calaway’s also had his chance to shine, although he’s nowhere near the same level as Dwayne Johnson.
Calaway made his film debut pretty early on into his wrestling career. He was in the 1991 film Suburban Commando, and has had guest roles in a couple of other films, not to mention numerous TV appearances. He’s not going to give Dwayne a run for his money any time soon, but it’s still something else he can put on his résumé.
11. MMA Involvement
If you’re a fan of MMA and watch all the big events, you’ve probably seen Calaway make an appearance. He’s never actually stepped into the octagon, and is probably a little long in the tooth right about now, but should he choose to do so, he’ll be more than capable of handling himself against any opponent. That’s because Calaway’s trained in MMA for a very long time, more specifically in Brazilian jiu-jitsu. He’s trained under the legendary Brazilian jiu-jitsu practitioner, Rolles Gracie, and was such an accomplished fighter, remarkably he earned his black belt in 19 months back in 2011, and that’s when he had to juggle it with all of his wrestling commitments!
Calaway just loves everything about MMA. He has a huge amount of understanding and respect for what being an MMA competitor entails, and is pretty tight with a lot of the pros out there – with the exception of Brock Lesnar. He’s just a real MMA nut, and perhaps he could get involved with MMA in another capacity now that he’s retired from wrestling.
10. Loves Boxing
Calaway might be an MMA nut and might be practiced in the art of MMA, but he’s just obsessed with fighting in general – whether it’s wrestling, MMA, or boxing, he just loves it.
In addition to MMA and wrestling, he also knows a bit of kickboxing, having been taught by his wife, Michelle McCool, who was an avid kickboxer before her wrestling days. This is one fighting family you don’t want to mess with!
You can see Calaway at big MMA events, but if there’s a massive boxing fight, you can bet your bottom dollar that Calaway’s going to be in attendance. When boxing superstar Manny Pacquiao faced Velázquez in 2005, it was Calaway who led Pacquiao’s team to the ring, as the flag bearer, carrying the U.S. flag. He also got a front row seat for that famous Lennox Lewis vs Mike Tyson fight in 2002, and has attended a number of other big fights over the years.
9. A WWE Favorite
In today’s day and age of professional wrestling, it’s very unusual for someone to stay with the same promotion for over a decade. Anyone who manages that, well, it’s pretty good going. Even the best who wrestle with the world’s top promotion, WWE, eventually move on, with the exception of a few stalwarts, like John Cena and The Big Show – these guys are practically part of the furniture in WWE they’ve been around for that long. But The Undertaker was around for longer, way longer, and he didn’t chop and change promotions either – when he got a contract with WWE, he remained with WWE until his last match in pro wrestling; now that’s what you call commitment. He joined the promotion way back in 1990, and over the years, established himself as a WWE legend with Vince McMahon, Triple H, and his cronies. That means, until he retired from the ring a month ago, he’d been drawing a paycheque from WWE for the last 27 years! That’s a hell of a long time to stick with the same promotion, but credit to him for recognizing WWE’s where he belonged, and to WWE for managing to hang onto him for all those years.
8. He Was The Main Man
As The Undertaker gradually began to rise through the ranks and grow with WWE, he established himself as one of the main men within the promotion – what he said went. He had a ton of backstage clout, and was a very influential figure. Unlike others, he didn’t need to bully people – it was just the respect that he commanded that meant he was essentially able to run things his way. People listened to him, and actually, WWE was all the better for it; it’s horrible to think what it would’ve been like if Triple H, Shawn Michaels, and The Kliq had things ALL their way! Triple H may have been stuck to Vince like glue, but The Undertaker was also very close to the main man. They were pretty tight throughout his time with the promotion, and so The Undertaker can be credited for a lot of what went on in WWE back in the day when he was at the forefront of the promotion, and he probably twisted Vince’s arm a few times too and caused him to ditch some of his ludicrous ideas, and for that, we thank him.
7. Family Connections
Because The Undertaker was such a unique gimmick, and pretty much stood alone doing that whole Deadman thing, it’s fair to assume that he was actually on his lonesome in wrestling, that he got into the industry by himself and didn’t have any family connections. That’s not the way it tends to work nowadays. Normally there’s some family member or other who’s already on the wrestling scene, who inspires you to follow in their footsteps. Or, you become the source of inspiration to others in your family, and other family members follow suit.
The Undertaker does actually have family within wrestling. Of course, there’s his wife, Michelle McCool, who was a prominent diva in her day. But he also had a cousin in the wrestling business, a guy who followed in his footsteps. Take one look at Brian Lee and you can tell he’s Calaway’s cousin. He had 15 years in the industry with the likes of TNA and WWE, where he played the imposter version of his cousin, the imposter Undertaker, but that’s pretty much all he was known for in wrestling.
6. He Is All About Animals
The Undertaker isn’t all about bringing doom and gloom. He might seem hardcore outside the ring too – that’s because he is – but there is a softer side to Calaway, something he’s really passionate about and has been for pretty much his whole life. He loves animals, but it’s his canine friends that have a special place in his heart. He wanted to do something to help dogs in need, help owners who couldn’t afford to get their pet pooches treated, and so he established a charitable organization. It was with his second wife, Sara, he set up the charitable fund. The Zeus Compton Calaway Save The Animals fund was set up specifically to help pay for the life-saving treatments of large breeds of dogs, and it sure has helped out a lot of dogs and their owners over the years who couldn’t afford to pay for essential procedures. It was set up following the death of their beloved Mastiff, Zeus – they knew what others were going through too.
5. Basketball Endeavours
It’s really weird to think of The Undertaker as basketball player, doing his thing on the court in the pro circuit. He just doesn’t look the type, even when he was young. Sure, he was tall, at least he had that going for him, but aside from that he was really quite dorky looking, and didn’t fit the bill, and certainly didn’t look like he’d be interested in sports at all, let alone basketball and wrestling. But Calaway was actually pretty good, and at one point, considered pursuing basketball as a legitimate career option. He started getting into basketball in high school, and that’s when he knew he wanted to do something in sports. He got into Angelina College on a basketball scholarship, then went to Texas Wesleyan University, majored in sport management, and that’s when he started getting heavily involved in basketball. He played for the uni’s basketball team, dropped out to focus on basketball full time, and was even making plans to go and play in Europe, before, seemingly out of nowhere, he switched his focus to wrestling.
4. The Deadman’s Scared Of Cucumbers
If you found yourself incredulously shaking your head as you read this title you wouldn’t have been the only one. Yes, arguably one of the scariest dudes in wrestling, a man who’s adopted that whole Deadman persona and fears nothing, well, actually does fear something, but it’s not what you’d expect would be able to get Calaway’s heart racing, to get those palms sweating. The Undertaker is in fact, pretty terrified of a humble vegetable, the cucumber. Needless to say it’s an irrational fear, but Calaway has his reasons. We don’t know how his fear, his aversion to cucumbers started, but he certainly tried to keep it under wraps – he wouldn’t have wanted everyone knowing cucumbers spook him! But Paul Bearer made the discovery. He was messing around, just doing what wrestlers do, and decided to fill Calaway’s hat with cucumbers as a prank. Apparently, the Deadman ran a mile while shouting he was about to vomit. If only some of his opponents over the years had known this, they could’ve used it to their advantage.
3. He’s A Very Religious Man
If you’ve seen The Undertaker wrestle over the years, you’ll know that he’s a pretty religious dude. It kind of ties into that whole Deadman persona, rising from the dead, that kind of stuff, and he’s incorporated plenty of religious storylines into his persona, the Ministry of Darkness. His ring entrance music had a funeral march theme, he’s used crosses and coffins numerous times over the years during his matches, and even kidnapped Stephanie McMahon and strung her up to a cross in a kind of crucifixion angle. All of this may be a part of his gimmick, but he’s actually a very religious man in real life too. Because of his religious beliefs, it’s actually made him pretty uncomfortable at times, portraying the Deadman gimmick and doing some of what he’s had to do over the years, some of what’s just been mentioned. But he’s learned to live with it, and probably by now, it’s become second nature.
2. Bone Street Krew
In the mid to late 90s, The Kliq basically ran things in WWE. Massive personalities such as Shawn Michaels, Kevin Nash, Triple H, Scott Hall, and Sean Waltman got together to run things in the locker rooms, stick together, and basically look out for each other. They didn’t care who came into their path, The Kliq were always going to rise to the top. It worked too, because with the exception of Waltman, they all became pretty big deals in wrestling and did quite well for themselves.
The Undertaker had a complicated relationship with members of The Kliq. He was friends with some, despised others, and so decided to set up his own crew to try and rival that of The Kliq. He formed the Bone Street Krew, consisting of Yokozuna, both Godwinns, Savio Vega, Crush, and The Godfather – a line up that’s pretty embarrassing when comparing it to the established members of The Kliq. It didn’t really take off, and although The Undertaker continued to have his say so, the whole BSK concept fizzled out.
1. He Didn’t Arrive As The Undertaker
You think of Calaway and you think of The Undertaker. There aren’t any other gimmicks that come to mind, no other personas he’s tried his hand at, just the Deadman. But he didn’t stumble on The Undertaker right away; it took plenty of trial and error in order to find the right gimmick and the right character that fitted Calaway down to a tee. In fact, he actually cycled through six personas before he and WWE finally found the one that worked, one they could envisage becoming a success, and settled on that famous Undertaker gimmick we now all know and love. Calaway began his wrestling career as Texas Red, then became the Master of Pain and subsequently The Punisher, an ex-con who was all about retribution – something out of a movie. Then there was Mean Mark Callous and Punisher Dice Morgan when he was in Japan, none of which took off. It just goes to show, if at first you don’t succeed or it doesn’t come your way, try, try and try again!