For over 25 years, The Undertaker has truly lived his gimmick. No, he doesn't live in coffins or anything like that, but the air of mystery that encapsulates The Phenom is just as thick as the smoke that fills the arena when he stalks his way to the ring.
Even when he revealed more of himself as The American Bad Ass, he still seldom gave interviews and spoke out of character. As a matter of fact, just about every 'Taker story out there (and on this list) is usually confirmed by hearsay and conjecture of other people involved, and The Deadman has yet to confirm a lot of what has been written about him. He hasn't even confirmed if he's actually married to Michelle McCool or not!
All kidding aside though, this is a list dedicated to his friends in the business. The ones that like to regale us fans with stories of The Demon of Death Valley. Perhaps one day he'll finally break kayfabe and let fans know about just how crazy some of these stories are and even more still confirm his friends in the business.
15 Brock Lesnar
Has any other superstar had more of The Undertaker's number throughout his entire career than The Beast Incarnate? From his early days in 2002 and 2003, and of course ending The Streak. Brock Lesnar is the only Superstar who has more Ws than Ls against The Deadman. Despite having a few disagreements over the years, The Undertaker would continually put the guy over if he didn't think the world of Brock.
He even handpicked the Mayor of Suplex City to end The Streak in 2011, which if you're keeping score was three years before WrestleMania XXX. The Phenom has stated that if he came up in the business now, he might have tried giving MMA a shot, and of course he has incorporated all kinds of MMA moves into his repertoire.
The profound respect that he has for the entire genre extends to the respect that he has for Lesnar and vice versa, as evidenced by a video of the two briefly exchanging their own brand of well wishes before The Deadman's assault on Bray Wyatt at WrestleMania 31.
14 Jim Ross
There once was Gordon Solie, then there was Gorilla Monsoon and Jesse Ventura, then Gorilla and Bobby Heenan. Then Jim Ross. Much like other in-ring Superstars that had to fight and claw their way to the top, Jim Ross had to survive being fired, twice no less, before becoming the voice of an entire generation!
Ross was more than just the commentator of the Attitude Era. He was also the head of talent relations at that time and he had a lot of hard choices and tough actions to take. On The Ross Report Podcast, Ross has spoken about he'd ask the Conscious of the WWE to help him out in enforcing those decisions, something The Phenom would assist with, certainly not part of The Undertaker's job description!
Ross would have the honor of calling many of The Phenom's most memorable matches, even when they were on different shows. The Reaper of Wayward Souls hold Ross in the same high regard that he held Paul Bearer, and thinks he's a genius in the business. How many people could get away with calling The Undertaker, Booger Red? Ross can.
13 Shawn Michaels
If you thought threatening to beat the holy hell out of a man would keep you from being friends, then you just don't know the wrestling business. Nineteen years ago, Shawn Michaels was set to take his much needed sabbatical, which at the time, no one knew if it was going to be a permanent vacation or not.
Facing Steve Austin at WrestleMania XIV, good ol' HBK was being a bit of a scamp leading people to think that he wasn't going to do the honors for Stone Cold, which left The Phenom no choice but to threaten to make sure HBK would drop the belt if he wasn't going to follow the plan. Obviously that didn't happen, and the fact that it didn't coupled with Shawn Michaels becoming a humble and honest man has allowed the two legends to mend epically broken fences of the past and go on to have not one but two of the greatest WrestleMania matches of all time.
12 Chris Jericho
There’s only one other WWE Superstar who has reinvented himself more than The Deadman and that’s Chris Jericho! Jericho is enjoying a one of the best years of his career, certainly his best since doing the honest man shtick a few years back. He has often compared The Phenom with Madonna for his ability to change and alter his persona and always stay relevant. However, Jericho is no slouch either. The fact that 'Taker hasn’t killed him yet for calling him Madonna must mean that The Undertaker and The Keeper of the List must be friends.
And they have been for a long time, mending a wound Jericho created for himself and his early WWE career when he called the longtime locker room leader boring. Thankfully, The Deadman was in the back during a house show which saw him have to get his friend back out of the crowd after some stupid idiots pelted him with batteries.
11 Triple H
They are the two most tenured members of the WWE roster. The Undertaker and Triple H have waged wars with one another over the years, most famously inside New York City’s Penn Station and of course the End of an Era Hell in a Cell match at WrestleMania XXVIII.
But had The Game continued his Kliq-ish behavior (re: The Undertaker did not approve of the Curtain Call and other Kliq antics), The Deadman might have and could have buried him. That is one burial that would have conceivably altered the entire wrestling landscape as we know it – no marriage to Steph, no NXT, no Papa Hunter. Once that thought is done sinking in, depending on how you feel about The Cerebral Assassin, thankfully, the Curtain Call was just a moment in time for Hunter and not indicative of what he would mean to the business and what the business meant to him.
Once getting to the mountain top, he again earned The Deadman’s friendship and through the years, Hunter has named checked The Phenom as the guy in the industry he respects the most. As for The Undertaker’s part in their friendship – for a guy who seldom breaks kayfabe, he’s done it several times for Helmsley, appearing all over the Thy Kingdom Come documentary. Not to mention their embrace along with Shawn Michaels after the Hell in the Cell match.
10 Brian Lee
Prime Time Brian Lee made a decent career for himself on the independent circuit before coming to the WWE. Most famously in Smokey Mountain Wrestling where you can earn double trivia points – he was not only their first ever champion, but the first person Sunny ever valeted for.
When The Phenom was sent to the heavens at the hands of Yokozuna and about 153 other heels at the 1994 Royal Rumble, Vince had dreamt up a wild storyline that would eventually see and impostor, “Underfaker” return, until the real deal came back to reap the false Deadman’s soul.
But where in the world could you find someone who remotely resembles the 6-foot-10 inch 300 plus pound Phenom with gigantic tattoo sleeves? How about his cousin, Lee who looks more less enough like The Reaper of Wayward Souls, give or take an inch and a tattoo.
Being family doesn’t necessarily make you close, however in this case, their familial connection certainly helped Lee’s career and gave us a memorable albeit weird AF SummerSlam main event.
9 Jake "The Snake" Roberts
One of the reasons for The Phenom’s early success in the WWE was the fact that he more or less walked up to anyone and everyone he could and soaked up their knowledge like a sponge. And it is a fairly universal fact that there are very few more sponge – worthy people than Hall of Famer Jake "The Snake" Roberts.
Some early and memorable Undertaker moments include The Deadman partnered with Jake in making The Ultimate Warrior and Macho Man's respective lives living nightmares. That was until The Deadman decided Roberts was too sick even for him, leading up to their match at WrestleMania VIII. Backstage, Roberts certainly spent a lot of time teaching The Reaper of Wayward Souls how to speak softly and inspire fear in everyone and anyone they did business with.
More importantly, as far as social life goes, Roberts' knowledge was far greater than The Phenom could ever imagine - he knew where all of the strip clubs were and according to Jake, he knew where they were all over the world.
In one of the instances where the hype machine didn't alter history too much, WCW had re-branded their Blond-Surfer-Neon-Colored champion, Sting into a dark and brooding crusader waging war against the nWo. Both he and The Undertaker were the respective dark avengers for their companies.
Being the two stalwarts for their respective companies had kept the two apart for years and Sting had made it known that he wanted to work with The Phenom at WrestleMania. But unfortunately, one of wrestling's greatest dream matches is now lost to the hourglass of time. But that doesn't mean their admiration and respect for one another is lost to time.
The duo, who both got their respective starts in World Class and USWA were reunited. The two shared a locker room at WrestleMania 31 and shared a plane ride home together back to Texas. They might have missed the boat on their epic encounter, but neither seems to mind too much as their friendship grows.
7 John Bradshaw Layfield
Brash and braggadocios, JBL speaks his mind on just about any topic he could think about. A trait fans didn't see much of when he was a member of The Undertaker's Ministry of Darkness. Backstage, the former Justin Hawk Bradshaw might not have been an official member of the Bone Street Krew, but he was certainly a known associate.
Nowadays on commentary, the legend might waiver on his outlooks on some Superstars, but his respect, love, and admiration of The Deadman is actually refreshing to hear, because it comes from a very real place. In one of the more grandiose friendships on this list, Bradshaw asked for and received The Undertaker to stand up for him as part of his wedding to Meredith Whitney. Imagine having to send that invitation to Death Valley.
6 Kurt Angle
If threatening someone wouldn't kill a friendship, then certainly choking someone out would, wouldn't it? Not in the wrestling world. In one of Vince McMahon's crazier moments, he thought it would be a good idea to try and take down the Olympic gold medalist and The Chairman came after Kurt Angle with all of the gusto that he had.
When The Phenom took ntoice, all he saw was his boss being pummeled by Angle and like the good lieutenant that he was, choked Angle out. Once everyone knew what really happened, a good laugh was had by all.
By most people accounts, the Wrestling Machine is a salt of the earth type person and so is The Deadman, so why wouldn't they be pretty close? Many people have cited Angle's ability to pick up the business faster than anyone they've ever seen, because The Phenom was showing him the ropes, and throughout his TNA run, Angle remained in contact with his mentor and friend.
5 The Hurricane
Here we have one of the several WCW stars able to reinvent himself and have a decent WWE career as one of the last WCW Cruiserweights. Gregory Shane Hurricane Helms was able to parlay his skills and add memorable character to his repertoire. The infamous "whatsupwithdat" catchphrase saw s star born, but built from the ground up.
According to Helms, we and he have The Deadman to thank for that. Both being on the SmackDown roster, they became close and had a mentor/mentoree type of relationship. According to the former superhero, The Phenom admired Helms in the ring and also helped him learn the subtleties of being a WWE Superstars. One of those subtleties of being a WWE Superstar may have helped The Hurricane become the longest reigning Cruiserweight Champion of all time.
4 Bret Hart
Universally thought to be one of the best ever, Bret Hart had in-ring career spanning nearly 30 years, earning nearly every accolade one can earn. The Hall of Famer has another unique accolade - he was part of The Phenom's first match at the 1990 Survivor Series. By all accounts the two were friends backstage ever since.
According to Hart, 'Taker was waiting for the chance to work with The Hitman because it would be the first time he would be able to show how well he could work, as opposed to being a lumbering undead zombie. Their friendship was built on respect. Supposedly, it was The Phenom who had Vince go find Bret to talk after the Montreal Screwjob. When Owen Hart's accident happened, 'Taker was on the first flight out to Calgary to be with his friend.
When Bret came back for WrestleMania XXVI, The Hitman was really looking forward to heading to the bar and kicking back a few with his old friend.
3 Big Show
As evidenced by just about every other big man that came before him, Big Show probably knew that sooner or later he'd be in The Phenom's crosshairs. Sure enough, not long after debuting back in 1999, "The Largest Athlete in the World found himself sitting under the learning tree of The Deadman. Backstage, too as The Phenom took it upon himself to help make Big Show reach his potential.
WCW had booked him as "Andre's son," but in truth he was as evergreen as they come until The Undertaker got his hands on him. Eventually he would begin to treat Show as an equal and as a friend. They became such good friends that after their Casket match in 2008, Show texted The Undertaker to thank him for helping him throughout his career. The response, as some of your own friends might do - he shot Show a picture of his testicles.
2 Kevin Nash
Before The Phenom and Big Daddy Cool, there was a very real misconception that big guys could not work worth a damn. Naturally, the two giants connected on that level while both shattering that stigmatism. In fact rumor has it that Diesel was tapped to defeat The Undertaker in their match at WrestleMania XII.
One would assume that the two had a minor falling out due to Nash being with The Kliq and 'Taker with BSK. As you know, the locker room leader was not too keen on The Kliq's antics. However, 'Taker and Nash have made up in recent years.
The most popular story of the two the has gone around is their mutual love of strip joints. Even after Vince asked his roster to stop going to them, Nash and 'Taker would continue to find the best ones in town, The Boss' rules be damned.
Both as members of BSK, Mideon, Dennis Knight turned being a lackey for The Deadman into a memorable run in The Ministry of Darkness, which probably stayed his "future endeavored" status. After spending time as the dimwitted pig farmer, Phineas Godwinn probably wouldn't have lasted long in the Attitude Era, but his friendship with The Deadman got him the gig as the "Eyes of the Ministry."
After the Ministry angle ended, Mideon found himself in a gimmick where he would streak through crowds wearing just a fanny pack. He left the business after the Naked Mideon gimmick ended, despite 'Taker trying to talk him out of it.
Nowadays, Knight is in the restaurant business, but his friendship with The Phenom has endured, and he maintains contact his former cult leader.
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