The Undertaker is without a doubt the single most iconic figure in the history of professional wrestling. A mixture of talent, time, and sheer dedication to craft and character has pushed him beyond the ranks of Hulk Hogan and The Rock and he will surely be remembered as one of the greatest of all time whenever he decides to hang up his boots. Mark Calaway, the man behind The Undertaker character, is an old-school guy and has broken character only on rare occasions over the years. Only recently has Calaway been making far more public appearances and giving more interviews and opening up about his life. As he has done more podcasts, interviews, and media, fans have gotten to see The Undertaker in a way like they never had been able to see him before when he adhered to his gimmick.

However, it isn’t just the fans who have struggled to get close to Mark Calaway. Many of his co-workers have been unable to establish anything beyond a professional relationship with The Deadman. There are a number of reasons for this, the most obvious being The Undertaker's dedication to his role as a locker room leader. He cannot be an authority behind the scenes if he is best friends with everybody who signs a WWE contract. If he didn’t keep a safe distance from fellow WWE superstars outside the ring, anarchy and chaos would reign in the locker room.

That being said, a number of WWE superstars have managed to get close to The Undertaker over the years.

UPDATE: 2023/12/22 07:30 EST BY Benjamin Vieira

In retirement, The Undertaker has stepped away from the day to day bubble of pro wrestling but is still quite active in the wider landscape. Hosting his own Youtube channel called Six Feet Under With Mark Calaway, The Deadman still keeps in touch with fans via the channel and his one-man shows produced in conjunction with WWE. He's formed several long connections with wrestlers in the business too and we will dive into those here.

16 The Undertaker Had Long History With Paul Heyman

Great Foes On-Screen, Great Allies Off-Screen

• Paul Heyman and The Undertaker have been foes several times.
• They had a close friendship backstage.
• Vince McMahon shot down a pitched story between the two.

While The Undertaker and Paul Heyman have been at odds on WWE television for several years, Heyman has been a pretty important figure in The Deadman’s career. The two worked together during the late eighties, when the future Undertaker was still trying to find his footing in the world of professional wrestling.

As an on-screen duo, The Undertaker and Paul Heyman didn’t achieve a whole lot, but they managed to form a pretty strong bond behind the scenes. It is said that Heyman wanted to use his friendship with The Undertaker as a storyline point for The Deadman’s 2014 feud with Brock Lesnar, but Vince McMahon wouldn’t allow it, choosing instead to keep The Undertaker and Mark Calaway separated, which is likely for the best, as the storyline they chose was terrific regardless.

15 Ricky Starks Bridges The Gap Between AEW And The Undertaker

Starks Speaks With The Deadman For Advice

In one of the most shocking connections on the list, Ricky Starks spoke in 2020 on AEW's Unrestricted Podcast about his connection with The Deadman:

“I used to go to a gym in Austin whichever year that was where Undertaker was wrestling Shane. He was getting ready for that. I want to say 2016. That’s how I initially met Taker at that gym. We would always work out at that same time. At that time he was getting ready, he had a guy that was filming a documentary for him because he wanted something for his kids to see of the process of getting into it. I met him there. I talked to him. We kept in contact. Then Brandon, who was doing the documentary, wanted to do a documentary on independents on how things worked. So he followed us one week on a loop from San Antonio to Laredo all the way to Mexico to Monterey."

Starks mentioned that he later spoke with Calaway for hours, picking his brain about the business and asking for advice. He also helped him prepare for his match with John Cena at WrestleMania 34.

14 Jake “The Snake” Roberts Was Close With The Undertaker Early On

"The Deadman" Battled "The Snake" At WrestleMania 8

• Jake Roberts and The Undertaker used to travel with one another.
• Roberts' sobriety issues caused problems between the two.
• The Undertaker wanted Roberts to be the "Higher Power."

Like Paul Heyman, Jake Roberts was a crucial figure in The Undertaker’s early career, though Roberts probably had more to do with The Deadman becoming a star than Heyman did.

When he first signed with WWE, The Undertaker sought out Jake Roberts and requested to travel with him as he had been told The Snake knew all the good bars and strip clubs. Roberts has recalled warning The Undertaker that he was difficult to keep up with in terms of drinking and scandalous behaviour, but the young man was undeterred. After a couple of road trips with a constantly inebriated Jake Roberts, the aspiring Undertaker found himself a new travel partner.

It is said that The Undertaker pushed for Roberts to be brought back and revealed as The Higher Power during that disastrous storyline, but Roberts’ problems with drug and alcohol abuse made a return impossible.

13 Kevin Nash And "The Deadman" Had Issues During The Monday Night Wars

The Two Big Men Have Been Friends For Years

• Nash and The Undertaker had differences in regards to the Monday Night Wars.
• The two used to be good friends behind the scenes.
• Despite his issues with The Kliq, The Undertaker and Nash are now friends.

Kevin Nash and The Undertaker worked closely together during Nash’s initial run in the WWE. In fact, many former WWE officials have claimed that Nash was down to defeat The Undertaker at WrestleMania before news of his move to WCW broke.

As two big men fighting against the stigma that guys their size can’t work, Nash and The Undertaker became good buddies, frequenting strip clubs together even after being told by Vince McMahon that WWE employees shouldn’t be visiting such places.

The two had a bit of a falling out during Nash’s last days with the WWE as The Undertaker was growing tired of The Kliq’s notoriously unruly behavior, but it seems they have been able to put the follies of youth behind them and patch things up.

12 Charles Wright And The Undertaker Did Not Like The Kliq*

Both Were Members Of BSK, The Bone Street Krew

• The two had a mutual disdain for The Kliq while in WWE.
• They were close friends prior to being in WWE.
• The Undertaker recruited Wright to BSK, a group that rivaled The Kliq.

A part of wrestling history as two distinct characters, Papa Shango and The Godfather, Charles Wright has had one of the most inexplicably underrated careers in the business. The guy has feuded with the likes of The Ultimate Warrior and captured the WWE Intercontinental and Tag Team championships. While much of Wright’s success is the result of his own hard work and talent, he owes a portion of it to The Undertaker.

Charles Wright and Mark Calaway were close friends before Wright was ever signed to Vince McMahon’s sports entertainment empire. Recognizing his friend’s size and in-ring abilities as being similar to his own, Taker went to bat for Wright before WWE management and convinced them to his buddy a shot.

When The Undertaker began his infamously mysterious BSK, Wright was among the first people he recruited to join him in his resistance to The Kilq. The BSK has since transcended the locker room and entered into wrestling lore.

11 Mideon And The Undertaker Have Been Friends For Years

The Two Were Allies In The Ministry Of Darkness

• The Undertaker personally requested Mideon to be in The Ministry of Darkness.
• Mideon won the European Title while a member of The Ministry.
• Despite his best tries, The Undertaker could not convince him to return to WWE.

Performing under the ring name “Mideon,” Dennis Knight was one of the members of The Ministry of Darkness.

By the time the Attitude Era arrived, Knight had already been stuck with a series of unsuccessful gimmicks and it looked like he was on his way out of the company. However, The Undertaker, with whom Knight was close friends, intervened and insisted he be placed in The Ministry of Darkness stable. Vince McMahon complied and Knight received something of a stay of execution.

After the dissolution of The Ministry, Knight’s career once again suffered and he was repackaged with a gimmick that saw him streaking through arenas under the totally creative name “Naked Mideon.” When Knight decided it was time to walk away from the wrestling business, The Undertaker did all he could to talk him into staying, assuring Knight that he would get him a high paying, long-term contract from the office. Knight politely declined and though he is no longer active in the ring, he maintains contact with his former high priest.

10 Sting And The Undertaker Got Close When Sting Joined WWE

Unfortunately, A Match Never Happened Between The Two

• The two never encountered each other much before Sting joined WWE.
• The Undertaker and Sting shared a locker room at WrestleMania 31.
• Fans wanted a match to happen between the two for years.

Sting versus The Undertaker is a match professional wrestling fans have wanted for years. Given that the two have pretty similar characters and were major names in their respective companies during the Monday Night Wars, which pitted WWE against WCW in a battle for supremacy, a lot of fans assumed that the pair would have some problems. However, that is far from the case.

While The Undertaker and Sting had minimal contact in the years after WCW’s closure, Sting’s WWE debut pushed them together. The two shared a locker room at WrestleMania 31 and even flew home to Texas together.

Those who encountered The Undertaker and Sting during WrestleMania weekend reported the two were in high spirits and laughing and joking with each other, with no signs of animosity or tension. It is even said that they were discussing plans for their eventual in-ring encounter if it were to ever occur. Sadly, the match would never happen as Undertaker is now retired and Sting will retire from pro wrestling in 2024.

9 Jim Ross Is Close With Several Stars From WWE's Attitude Era

The Undertaker Specifically Requested Ross For WrestleMania 28

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• Ross has been close to several WWE stars, including Steve Austin.
• The Undertaker views him on the same pedestal as Paul Bearer.
• JR was The Undertaker's choice for commentary at WrestleMania 28 in his match against Triple H.

Jim Ross is one of the most revered figures in professional wrestling and is perhaps the only commentator to be treated as a main event level star behind the scenes. Ross was a prominent backstage figure during the 90s and 00s, which gave him the chance to develop relationships with top stars such as Triple H, Shawn Michaels, and The Undertaker.

The Undertaker has immense respect for "Good Ol’ JR" and holds him in the same esteem as he held Paul Bearer, viewing him as a wrestling genius the likes of which are unlikely to be seen again. Despite the fact he spent much of his career stationed on Raw while The Undertaker competed on SmackDown during the brand split, JR called many of The Undertaker’s most important matches and The Deadman specifically requested Ross be brought in to call his WrestleMania 28 encounter with Triple H.

8 The Undertaker Was The First Foe Of Mick Foley In WWE

The Two Friends Have Battled Numerous Times

• The Undertaker and Foley have gone to war several times against each other.
• Foley was famously thrown off Hell in a Cell by The Undertaker.
• They have always been close behind the scenes.

The Undertaker is one of the most important figures in Mick Foley’s career. When Foley arrived in the WWE, he was immediately put into a feud with The Undertaker over the loyalty of Paul Bearer. Taker elevated Foley to the main event and ensured Mankind took on a life of his own, removed from the gory legacy of Cactus Jack in WCW.

Of course, the most famous encounter between the two came when The Undertaker tossed Foley off the top of the Hell in a Cell. According to Foley, "The Deadman" really did not want to go through the spot and tried to talk him out of it in the lead up to the match, but eventually went with it because he had so much respect for the hardcore legend and trusted him to pull it off successfully.

In the years since that match, The Undertaker has expressed his bafflement at the fact that Foley is able to stand after all the punishment he has absorbed. While the two were some of the biggest rivals of the Attitude Era, they are real friends off-screen.

7 The Undertaker Went To Bat For Bret Hart

The Undertaker Supported Hart During The Montreal Screwjob

• Bret Hart had a lot of trust in The Undertaker.
• The Undertaker went to Vince McMahon for answers after the Montreal Screwjob.
• The two have immense respect for each other. When Hart returned to WWE, he had missed The Undertaker a lot.

According to Bret Hart, The Undertaker is the only guy outside his brother Owen that he could rely on backstage. When Shawn Michaels and Triple H were busy turning the entire locker room against the Hart family, The Undertaker was busy making sure personal feelings did not get in the way of what was best for the business.

In the moments after The Montreal Screwjob, when Vince McMahon infamously stole the WWE World Championship from Bret Hart, The Undertaker was the only person who demanded answers from the boss. It has been said that The Undertaker, one of Vince McMahon’s most loyal employees, contemplated leaving the company out of respect for Hart, though that didn’t happen.

Reflecting on his return to WWE, Hart declared one of the most pleasing moments of his homecoming to be sitting at the bar with The Undertaker and kicking about old times.

6 The Undertaker And Brock Lesnar Have A Storied Rivalry

"The Beast" Ended The Legendary WrestleMania Streak

• The two had a legendary encounter at UFC 121. They went on to have one of the biggest feuds in WWE history.
• The two faced off at WrestleMania 30, where Lesnar ended The Undertaker's WrestleMania streak.
• They had a series of matches against one another in 2015, with Lesnar winning their trilogy 2-1.

Everybody has seen that video of The Undertaker and Brock Lesnar at UFC 121. While Taker is discussing his thoughts on Brock Lesnar's loss to Cain Velasquez, a passing Brock Lesnar makes eye contact, prompting the fearless Deadman to ask “You wanna do it?”

It resulted in much speculation among WWE and UFC fans as to why The Undertaker and Brock Lesnar were not on good terms and many expected the two to refuse to work together when rumors first began to spread of an impending feud in 2014.

However, it seems The Undertaker and Brock Lesnar have managed to overcome whatever differences they had during UFC 121 (though it might've been staged) and are by all accounts now close friends. After years of breathtaking bouts inside the ring, The Beast and The Deadman share an immense level of respect for each other.

5 Triple H And The Undertaker Have Nothing But Respect For One Another

The Two Defined An Era Of WWE

• Triple H faced The Undertaker three times at WrestleMania.
• They had tension early on due to Triple H's membership in The Kliq.
• WrestleMania 28 saw a genuinely emotional moment between the two pillars of WWE.

The Undertaker and Triple H have had their problems over the years. Taker did not take kindly to the infamous Curtain Call when Hunter, along with his fellow Kilq members, broke kayfabe to have a pseudo-emotional moment in the ring with Kevin Nash and Scott Hall, who were leaving for WCW.

However, several years later, when Triple H was pushed to the main event, he began to win The Deadman over. The pair had a series of stellar encounters, and together they saw their contemporaries drop off one by one. Eventually, The Undertaker and Triple H were left as the last of a dying breed and were entrusted with maintaining order in the locker room.

The pair shared a genuinely emotional moment after their match at WrestleMania 28, with both men admitting they had their doubts if they could still go inside the ring and thanking the other for bringing out the best in them.

4 Gregory Helms Is An Unlikely Friend Of "The Deadman"

Helms And The Undertaker Have Massive Respect For Each Other

• Helms learned a lot with The Undertaker as a locker room leader.
• Helms went onto become the longest-reigning WWE Cruiserweight Champion in history.
• "The Deadman" showed Helms the right way to hold a title.

Gregory Helms seems like a strange entry on this list, considering he and The Undertaker are from two different generations, but he is one of many younger wrestlers to have benefitted from being on SmackDown at the time of The Undertaker’s blue brand leadership.

In shoot interviews since leaving WWE, the man who was once known as "The Hurricane" has discussed The Phenom’s role in molding him into a WWE superstar. According to Helms, The Undertaker acknowledged his incredible skills in the ring but took it upon himself to teach the young man a couple of basic things that would improve his performances tenfold, including the right way to hold a championship. Helms went on to become the longest reigning WWE Cruiserweight Champion of all time, so The Deadman must have gone to bat for him with company officials.

3 The Undertaker Gave Big Show Respect That Many Did Not

The Duo Were WWE Tag Team Champions

• The Undertaker helped to show Big Show the ropes in WWE.
• The two were both friends and foes while in WWE.
• Big Show was always thankful for The Undertaker's help in his wrestling career.

When Vince McMahon first hired Big Show, he was ecstatic. He had managed to sign a guy who had the potential to be the next André the Giant, a one of a kind superstar people would attend live shows to see in person. The one problem was Big Show was green. To remedy this, McMahon stuck Show in a tag team with the far more experienced Undertaker, who took Big Show under his tattooed wing and thought him the ways of the mat.

Their partnership evolved into a close friendship and it wasn’t long before The Undertaker treated Big Show as somebody who was on his level instead of some guy who still needed to learn to wrestle. The two went on to have a series of memorable rivalries and always seemed to have fun working together.

Recently, Big Show shared a story about his 2008 casket match with The Undertaker, which he regards as his best performance. After the match, Show texted The Undertaker to thank him for helping him reach his full potential. This was an earnest if somewhat soppy message and probably not the kind of thing The Deadman was used to receiving. According to Big Show, ‘Taker replied not with words, but with a picture of his testicles.

2 The Undertaker Put On Classic Matches With Shawn Michaels

The Two Were Apart Of One Of WWE's Greatest Rivalries

• The Undertaker and Shawn Michaels have a rocky history with one another, but are now friends.
• When Michaels was going through issues backstage, The Undertaker was the only one who would stand up to him.
• The two wrestled a pair of classic matches at WrestleMania 25 and WrestleMania 26.

We’ve already discussed The Undertaker’s disdain for The Kliq and all those involved with it, so it is no surprise that The Deadman has had some well-documented issues with the group’s leader, “The Heartbreak Kid” Shawn Michaels.

During the 1990s, when Michaels was off his head on drugs at any given moment and refusing to do what was asked of him, The Undertaker was the only person with the pull or courage to stand up to him (at least after Bert Hart left). According to legend, The Undertaker made it clear to Michaels that were he ever to go against what was planned at WrestleMania XIV, where he was scheduled to lost to Stone Cold Steve Austin, he would have him to answer to.

Over the past couple of years, however, The Deadman has managed to form a tight friendship with a sober Shawn Michaels. The two participated in what is considered by many to be the greatest wrestling match of all time at WrestleMania 25 and Michaels’ respect for The Deadman was so strong that he requested he be the one to retire him the following year.

1 Vince McMahon & The Undertaker Have Always Had A Close Relationship*

The Undertaker Is McMahon's Favorite Wrestler

• The Undertaker was always loyal to Vince McMahon and WWE.
• He wrestled for WWE for decades.
• McMahon asked for Brock Lesnar to end the legendary WrestleMania streak of "The Deadman."

Vince McMahon has gone on record as saying The Undertaker is his favorite wrestler of all time, something which didn’t surprise many. The Undertaker has been loyal to Vince McMahon ever since his WWE debut at Survivor Series 1990. He has carried the company through tough and tougher times and has always done what was requested of him, including putting Brock Lesnar over at WrestleMania XXX, sacrificing his famed WrestleMania undefeated streak.

The respect McMahon has for The Undertaker is reciprocated by The Deadman, who has given over 25 years of his life to the betterment of the man’s company. It was rumored that the two had fallen out over a disagreement about plans for WrestleMania 32, with some saying The Undertaker had told McMahon he would never wrestle for him again.

They had resolved their issues. During The Undertaker's retirement at Survivor Series 2020, McMahon said some words about him prior to "The Deadman" speaking to the fans in the ThunderDome.