The Undertaker’s Most Memorable WWE Moments

Wrestling | 11/1/19

Vince McMahon had built the WWE (then the WWF) into the biggest powerhouse in professional wrestling by the start of the 1980’s. Throughout the years he’s had a significant stable of stars including Hulk Hogan, Bret Hart, Shawn Michaels, The Rock, Steve Austin and John Cena.

But no star has had the kind of success and longevity as Mark “The Undertaker” Callaway. The multi-time champion is renowned for his agility, grace and massive size as well as his legendary Wrestlemania winning streak. Here are the most memorable moments from his career.

A Quite Normal Birth

a still of the undertaker as a child
Youtube
Youtube

While his WWE biography may tell you that he was born in the deepest, darkest pits of hell, Mark Callaway actually had quite a normal birth in Houston, Texas. Born in 1965, his parents were Frank and Betty and he had four older brothers.

He had quite an athletic childhood, normally sparring against his brothers David, Michael, Paul, and Timothy. A terrific athlete, Mark played both football and basketball at Houston’s Stephen Pool Waltrip High School.

A Tall And Agile Basketball Star

the undertaker in a boxing gym
Peter Byrne – PA Images/PA Images via Getty Images
Peter Byrne – PA Images/PA Images via Getty Images

Any regular watcher of the WWE could tell you that Mark Callaway is not only monstrously tall, he is also incredibly agile. These traits served him well in the sport of basketball, which he played in High School and College.

The Undertaker began his college basketball career at Angelina College before moving onto the NCAA’s Texas Wesleyan University. A standout, Callaway was offered the opportunity to continue his career in Europe but decided to focus on wrestling instead.

A Successful Debut

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Instead of playing professional basketball overseas, Callaway opted to begin full-time training for a wrestling career. The first organization the Undertaker worked for was known as World Class Championship Wrestling and was based out of Dallas, Texas.

When he began his career, he had not yet adopted his dark persona and was simply known as Texas Red. His first career match came against Bruiser Brody, which was ironic as Brody was also an extremely large and atypically athletic grappler.

Called Up To A Bigger Promotion

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YouTube
YouTube

After a successful run in WCCW that eventually saw him win the heavyweight championship, Callaway was soon called up to World Championship Wrestling (WCW). The promotion had big plans for him and he was given the name Mean Mark Callous by wrestling legend Terry Funk.

WCW quickly teamed Callaway with the similarly tall and athletic Dan Spivey and called the tag team The Skyscrapers. Callaway’s biggest WCW opportunity came in 1990’s Great American Bash when he was defeated by Lex Luger in a match for the US Heavyweight Championship.

A Trip Overseas

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KMazur/WireImage
KMazur/WireImage

The career of any successful wrestler is never complete until the grappler makes appearances wrestling in Japan. The Japanese audience is especially receptive to massive wrestlers, which made Callaway a perfect fit for the country.

The Undertaker wrestled for the New Japan promotion during 1990. He faced off against some world-famous competitors in his attempt to capture the Unified World Heavyweight Championship. While he was able to take out Bill Dundee he lost to eventual WWE co-worker Jerry Lawler.

A Trip To The Big Time

the undertaker in the ring
KMazur/WireImage
KMazur/WireImage

Amazingly enough, when Vince McMahon first scouted Mark Callaway, he wasn’t sure if he could cut it in the WWE. He was eventually talked into hiring him by talent scout and sometime performer Bruce Prichard.

Once Callaway was in the fold, it didn’t take the promotion long to figure out he was a compelling character. An important aspect of Callaway’s early character was that he was impervious to pain and he made his first big splash as a member of Ted DiBiase’s team at the 1990 Survivor Series.

The Undertaker Gets A Manager

paul bearer of wwe
WWE/YouTube
WWE/YouTube

With his immense size and incredible agility, the Undertaker burst onto the scene at the World Wrestling Federation. As he was yet to make a major impression on the microphone, the promotion felt it was best to tie Callaway to a prominent manager.

Experienced manager Bill Moody stepped in to create the character of Paul Bearer. Bearer was an unusual manager who hyped up the Undertaker’s supernatural abilities. The manager also carried an urn to each match which supposedly gave the Undertaker power over his opponents.

A Terrifying Way To End The Match

the undertaker has crazy eyes
Kevin Mazur/WireImage
Kevin Mazur/WireImage

With his massive size, tremendous wrestling ability, and macabre gimmick, the Undertaker was someone that no other wrestler wanted to face. But what happened to his opponents after the match was even worse.

For his first year in the WWE, Callaway would bring a body bag along with him to the ring. Once he ended the match by performing his tombstone piledriver finisher, the Undertaker would zip his vanquished foe into the bag and carry it back to the dressing room.

Youngest Champion Ever

the undertaker at a young age
The Immortal Deadman/YouTube
The Immortal Deadman/YouTube

After months of destroying wrestlers on the lower end of the card, the Undertaker began to become more of a draw for the WWE. He had his first Wrestlemania match in 1991, easily dispatching the legendary Jimmy Snuka.

Callaway then engaged in a feud with the biggest star in the game, Hulk Hogan. Amazingly enough, the Undertaker was able to defeat Hogan at the 1991 Survivor Series. Callaway, then 26, became the youngest WWE champion ever.

A Feud With A Snake

wwe jake the snake in the ring
Bruce Bennett Studios via Getty Images Studios/Getty Images
Bruce Bennett Studios via Getty Images Studios/Getty Images

The Undertaker ended up dropping his belt back to Hulk Hogan close to a week later. The deadman then began an alliance with a similarly dark wrestler in Jake “The Snake” Roberts. The pair ran roughshod over the promotion.

The partnership, however, wasn’t meant to be and the two began a major feud. The feud lasted for around two months and came to a culmination at Wrestlemania VIII where Callaway was able to dispatch Roberts and continue his undefeated Wrestlemania streak.

Another Title Reign

the undertaker in saudi arabia
AMER HILABI/AFP via Getty Images
AMER HILABI/AFP via Getty Images

The first title reign for the Undertaker only lasted for 6 days. He was able to capture his second championship in March of 1997 by defeating Psycho Sid at Wrestlemania XIII. He would then engage in a feud with Bret Hart.

The Deadman and the Excellence of Execution entered a program that also included Shawn Michaels. Michaels worked as the special guest referee when the Undertaker and Hart squared off at Summer Slam. The ref inadvertently hit Callaway with a steel chair and the title went to Hart.

The Undertaker Meets His Brother

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Alfredo Lopez/Jam Media/LatinContent via Getty Images
Alfredo Lopez/Jam Media/LatinContent via Getty Images

With the Undertaker being such a dominant force in the promotion, there were few wrestlers who could stand against them. Even if they were skilled grapplers, Callaway dwarfed them in sheer size. Until his brother came around.

In 1997, the Undertaker’s estranged brother told the world about his origins. Kane was silent, strong and gigantic, easily standing eye to eye with the Undertaker. For the remainder of their careers, the two would often feud and sometimes team-up.

The Perfect Rival For Hell In A Cell

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YouTube
YouTube

In addition to his brother Kane, the Undertaker also encountered a new rival in Mankind. While Mankind was a very large man, he wasn’t quite as big as Callaway. What he could match, though, was the Undertaker’s savage ferocity.

The most famous match between the duo came in 1998’s King of the Ring pay per view. The Undertaker memorably pile drove Mankind through the top of a steel cage and down on the mat 20 feet below. Callaway was able to notch the win in the brutally fought match.

The Deadman Gets A Posse

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YouTube
YouTube

After his memorable feuds with Mankind and Kane, the Undertaker was one of the most well-established superstars in the WWE. As a prominent grappler in the promotion, Callaway began to build up a posse with other successful wrestlers.

The other men in the Undertaker’s Ministry of Darkness featured similarly dark personas. Among the characters in the Ministry were Christian, Edge, Gangrel, Viscera, Farooq, Bradshaw and Mideon. Eventually, the faction disbanded and Callaway’s character took on a new persona.

A New American Nickname

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After years of taking on a dark and macabre persona, the Undertaker debuted a somewhat different look in 2000. Instead of tombstones and funeral music, Callaway began to come down to the ring riding a motorcycle while Kid Rock’s “American Badass” played over the PA system.

The motorcycle riding Callaway was just as devastating as the funeral parlor version. He joined Kane in a tag team known as The Brothers of Destruction. The pair feuded with Edge and Christian for the tag team titles.

The Deadman Dominates

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AMER HILABI/AFP/Getty Images
AMER HILABI/AFP/Getty Images

During the 2003 Summer Slam, the Undertaker was defeated by Mr. McMahon in a Buried Alive Match thanks to significant interference from Kane. After the loss, Callaway disappeared from the WWE for some time. When he came back, he was the Deadman once again.

And the Deadman continued his Wrestlemania winning streak while also seeking a new title. The next championship came in 2007 when the Undertaker defeated Batista at Wrestlemania XXIII. He later dropped the belt to Edge.

The Worlds Strongest Feud

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Youtube
Youtube

Besides his “brother” Kane, the WWE always had issues finding opponents who could physically match up with the Undertaker. Mark Henry certainly fit the bill, though. The former world’s strongest man measured in at 6-4 and 360 pounds.

Henry and Callaway engaged in a protracted feud that came to a head at Wrestlemania 22 in Rosemount, Illinois. The casket match between the two was both rugged and brutal. Eventually, the Deadman was able to dispatch Henry and place him in the casket.

The Streak Continues

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Gerardo Zavala/Jam Media/LatinContent via Getty Images
Gerardo Zavala/Jam Media/LatinContent via Getty Images

With his victory over Edge during Wrestlemania XXIV in 2008, it became clear that the Undertaker had created a pretty incredible 16 year run of wins. To keep his Wrestlemania winning steak intact, Callaway would have to defeat some significant contenders in the coming years.

First came Shawn Michaels who the Undertaker beat in the next two Wrestlemanias. Then, Callaway was able to dispatch Hunter Hearst Helmsley the following two years. During Wrestlemania 29 in 2013, the Undertaker was able to take out CM Punk, at that time the promotions biggest star.

The End Of The Streak

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JP Yim/Getty Images
JP Yim/Getty Images

If anyone was going to end the Undertaker’s unprecedented Wrestlemania winning streak, it would have to be someone as massive and aggressive as he is. The prime candidate came along in WWE regular and sometimes Ultimate Fighter Brock Lesnar.

Lesnar returned to the WWE after a very successful mixed martial arts career and set his sights squarely on Callaway. The two faced off at Wrestlemania XXX in New Orleans. In a back and forth and incredibly closely fought match, Lesnar was able to overtake the Deadman and end the streak.

A Sort Of Retirement

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Tim Warner/Getty Images
Tim Warner/Getty Images

Many thought that the end of the steak would spell the end of Mark Callaway’s incredible run in the WWE. The urge to wrestle, though, even part-time, has never stopped burning in the Undertaker.

He has fought in four Wrestlemania matches since the end of the streak, winning against Bray Wyatt, Shane McMahon, and John Cena and losing to Roman Reigns. Taker did not appear in Wrestlemania 35 which took place in New Jersey. This marked the first time he didn’t fight at the pay per view in 19 years.

He Learned His Signature Move From Don Jardine

undertaker signature move
JP Yim/Getty Images
JP Yim/Getty Images

The Undertaker’s signature move is known as “Old School.” During the move, the scary behemoth stands on the rope before crashing down onto his opponent. Callaway didn’t come up with the move though, he learned it from Don Jardine.

During his four-decades long wrestling career, Jardine was known as The Spoiler, and walking the rope was his signature move. The Undertaker adopted the move as his own. Today it is one of the most iconic moves in WWE.

He Was Going To Be The Eggman

wrestling
Moses Robinson/Getty Images
Moses Robinson/Getty Images

Where would the world of wrestling be with The Undertaker? Thankfully, that’s a question we don’t have to answer, but we almost had to. It’s true, The Undertaker was going to debut as The Eggman.

As fun as that sounds, it wouldn’t have suited The Undertaker. If he would have been this egg character, wrestling might’ve never been the same. Kane wouldn’t have had his brother and people wouldn’t be getting tombstoned. Think about that.

He’s Never Officially Lost In THIS Manner

mp submission
Getty Images
Getty Images

There are several ways to defeat an opponent while wrestling like a pin down and a submission. When it comes to submission, The Undertaker has never officially lost in that manner.

The only time that came close to that happening was in 2004 in a match with Kurt Angle. The Undertaker had him pinned while Angle had a grip on him. Undertaker tapped out as the pin count reached three so the referee called a draw!

He Almost Choked Out Kurt Angle For Real!

choking
Michael Loccisano/Patrick McMullan via Getty Images
Michael Loccisano/Patrick McMullan via Getty Images

Yes, wrestling is fake (don’t tell the kids), but one time, The Undertaker almost choked out Kurt Angle in real life. It sounds crazy, but the big guy didn’t know the real story.

Vince McMahon and Kurt Angle were in a battle of one-upping each other when they found themselves around a sleeping Undertaker. During one of their playful interactions, it became too loud and it woke up The Undertaker, who saw the two in a scuffle. He rushed Angle and nearly choked him out before knowing it was all games.

A Fear Of WHAT?

fear of something
Gilbert Carrasquillo/WireImage
Gilbert Carrasquillo/WireImage

Lots of people have irrational phobias, but you wouldn’t expect someone as manly as The Undertaker to be afraid of a vegetable. He has a great phobia of cucumbers, kind of like cats.

One of his traveling mates, Bearer, had to use the restroom really bad, but The Undertaker told him to fill the car up with gas first when they stopped. As a result he wet his pants and Undertaker told everyone. To extract revenge, Bearer filled The Undertaker’s hat with cucumbers and when he saw it, he freaked out and almost threw up!

He’s A Master Fighter

master fighter
KMazur/WireImage
KMazur/WireImage

Even if wrestling might be fake, The Undertaker isn’t a person you would want to take on in a fight, even if you were the same size or bigger. He’s a black belt in Brazilian Jiu Jitsu and a boxing fan.

Oh yeah, he’s also into MMA as well. He likes attending the fights and hanging out with other MMA fighters. His “Hell’s Gate” submission has some MMA inspiration behind it also, in case you were wondering.

Beef With Brock Lesnar

brock lesnar
JP Yim/Getty Images
JP Yim/Getty Images

The Undertaker’s beef with Brock Lesnar is more than meets the eye or anyone leads it on to be. The two had an exchange at UFC 121 after Lesnar walked past Undertaker after a fight.

Undertaker didn’t like that Lesnar left the WWE after he got built up to be the future. He was highly upset that he left and didn’t give the WWE any type of credit. Some people take things a bit personal.

He’s Been Married Many Times And Has Four Children

with woman
David Becker/WireImage
David Becker/WireImage

It seems like The Undertaker can’t hold down a relationship, but he sure knows how to keep his opponents under control! The big man has had three marriages and four children.

His longest marriage, which was also his first, was with Jordi Lynn. It lasted between 1989 and 1999 and they had a son named Gunner. After Lynn, he tied the knot with Sara and had two children with her. He’s currently with Michelle McCool.

Backstage Drama With Shawn Michaels

jumping off the edge
KMazur/WireImage
KMazur/WireImage

Shawn Michaels and The Undertaker have a rich history, and you already know that based on the slides from earlier. One thing we haven’t mentioned is the backstage drama they had.

Leading up to Wrestlemania XIV, Michaels sustained a back injury that would lead to him retiring, but he didn’t want to lose his title to Steve Austin that easily. The Undertaker confronted him and threatened to knock him out if he didn’t lose the match as planned. Michaels listened to the man afraid of cucumbers.

Kane Is His Biggest Opponent

wrestling
KMazur/WireImage
KMazur/WireImage

They’re the brothers of destruction and have been the most dominant tag team duo to ever fight in the WWE. Still, that doesn’t mean they don’t throw hands at each other from time to time.

Actually, they’ve fought more times than anyone can count on two hands. They’ve been in bouts 184 times with Undertaker taking home 106 victories. Kane might not be too happy about that record but what do you want him to do about it? n

He Loves Motorcycles!

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Tiffany Rose/WireImage
Tiffany Rose/WireImage

The Undertaker looks like he enjoys a good bike ride. The wrestler is an avid motorcycle fan who collects West Coast Choppers and Harley-Davidsons. He bought his first brand new bike after beating Hulk Hogan for the WWF Championship.

The guy does enter the arena on a bike sometimes, so that pretty much sums up his love for the vehicles. Not everyone can pull that off, but not everyone is going to challenge what The Undertaker does.

Lending His Home To Celebrities

walking in
Gaye Gerard/Getty Images
Gaye Gerard/Getty Images

The Undertaker has a pretty handsome net worth thanks to all his years contributing to the WWE. That means he’s able to purchase some fancy things like an expensive house.

His home was so lovely; he loaned it to Brad Pitt and Angelina Jolie once. “The best part of the house is a separate gym area with a real [World Wrestling Entertainment] ring in it,” contractor Ron Charlies, who worked on the home’s construction said. “I’m sure Brad and the kids horse around in it.”

His Taste In Music Is Quite Dark

Music the undertaker loves
Tiffany Rose/WireImage
Tiffany Rose/WireImage

Well, The Undertaker being a fan of dark music makes plenty of sense. His stage names revolves around darkness, if you couldn’t already tell and he’s always wearing black in some shape or form.

He’s a huge fan of Nick Cave, ZZ Top, AC/DC, Kiss, and much more. When he isn’t listening to artists like Black Sabbath, and Iron Maiden, he’ll switch things up to country music or the blues. Those are all very different genres.

The Man Loves Golf

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Gilbert Carrasquillo/WireImage
Gilbert Carrasquillo/WireImage

In an interview, The Undertaker said, “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 it.”

If he keeps that same attitude, he’ll never get better. We’re not saying he’s trying to be the next Tiger Woods, but maybe he should try and improve so he could stop tormenting himself.

His Original Name Was Something Else…

Kane the undertaker
KMazur/WireImage
KMazur/WireImage

At first he was going to be the egg guy, but that was never going to work out. Once The Undertake became his persona, he was going to have a slightly adjusted name.

He’s gone through a ton of name changes throughout his career, eight to be exact, but one of them might’ve worked. He had Texas Red, Punisher Dice Morgan, Commando, and the one that could’ve stuck was Kane The Undertaker. Has a nice ring to it, right?

He Won A Match Thanks To A DQ

the wrestler
Simon Galloway – PA Images via Getty Images
Simon Galloway – PA Images via Getty Images

It isn’t every day that you see a wrestling match end in a DQ but it happened with The Undertaker. During WrestleMania IX, Undertaker fought Giant Gonzalez, the man with unsettling attire.

In the match, Gonzalez acquired a cloth with chloroform so he could knockout The Undertaker! Wow, this would result in the DQ, giving The Undertaker his third consecutive Wrestlemania victory. It’s the only match involving Undertaker that resulted in disqualification that many people don’t talk about often.

Vince McMahon Didn’t Like Him At First

vince mcmahon
Simon Galloway – PA Images via Getty Images
Simon Galloway – PA Images via Getty Images

It’s hard to imagine the man in charge not liking The Undertaker at first. Undertaker would go on to become one of the most omnipresent figures in the WWE from 1990 onward.

Vince McMahon watched Undertaker’s match with Lex Luger at the 1990 Great American Bash, but he didn’t like what his eyes saw. He had an injury at the time, so he had to power through the match, knowing McMahon had his eye on him. McMahon later changed his mind after meeting the big guy one month later.

Working With The Hulkster

the hulkster
Stan Godlewski/Getty Images
Stan Godlewski/Getty Images

Before he would make his debut with the WWE, The Undertaker worked with Hulk Hogan in the arts world. Hogan released a sci-fi/comedy film called Suburban Commando in the fall of 1991.

Little did you know, The Undertaker had a role as a baby-voiced bounty hunter who tried and failed at attempting to snuff Hogan’s character. It might sound bad, but it was more lively than their matchup at Judgement Day 2002 but that’s not saying a lot.

Taking An Unlikely Defeat

with a belt
Bobby Bank/WireImage
Bobby Bank/WireImage

In 1991, the WWE filmed an event in Barcelona, Spain, that wasn’t televised in the states. It was Spain’s little secret, but footage finally surfaced thanks to this new digital era we live in today.

Undertaker was on path to square up against WWE Champion Hulk Hogan, but he took an unexpected loss. Mid-carder Tito Santana handed The Undertaker his loss in the main event of the show! Have you even heard of Tito Santana?

The Nod To Main Event Raw

with a legend
Moses Robinson/Getty Images
Moses Robinson/Getty Images

You can’t just let anybody be the main event of a new program, so it was smart of the WWE to select The Undertaker to have that privilege. The Undertaker took the lead in the first broadcast of Raw.

He had a two-minute cake walk match against wild-eyed Damien Demento. After that, he wold go on to main event many more of the broadcasts over the years. One of his matches had an insane amount of viewers.