The Undertaker: A Legacy Which Will Never Be Forgotten

Few have ever worked in professional wrestling that has embodied their character quite like The Undertaker. 

The Phenom was every bit of that moniker. In the early days of his tenure in WWE(F), he was a mysterious and daunting presence that both captivated and terrified audiences.

The Undertaker was more than a wrestler or a character; he was an entire persona that—for many years—no one could quite figure out. He was the living dead man, the one who took opponents to the grave.

When one thinks of wrestling entrances, the time that most use to showboat, sway the crowd, or emphasize their personality, The Undertaker’s is the inevitable talking point. A slow, methodical walk to the ring surrounded by smoke and fog in a darkened arena, while bells toll and ominous music chills the air. It was a sight to see, and every crowd that sat through it did so in amazement.

The Undertaker was the wrestler that no one could escape. Anyone that had a feud with ‘Taker was never quite the same again. His long-standing WrestleMania streak is one of the most impressive feats in wrestling history—winning 21 consecutive matches at the premier WWE event. WrestleMania happens once a year, so yes, that means that The Undertaker was undefeated on the Grandest Stage of Them All for 21 years.

Early Life

Mark Calaway was born on March 24, 1965, in Houston, Texas. The youngest of five brothers, Mark grew up in a large family. In high school, Calaway played basketball and football. He went to college on a basketball scholarship. He attended Angelina College in 1983, but two years later, in 1985, he enrolled at Texas Wesleyan University. He played center for the Wesleyan basketball team and majored in sports management.

Calaway dropped out of college to focus on a professional sports career and contemplated trying his hand at going pro in basketball in Europe. Ultimately, Calaway decided to pursue his passion for wrestling and began training in 1986.

How the Undertaker started wrestling

Start in Wrestling

Mark Calaway’s start in professional wrestling wasn’t a smooth one. He trained under Buzz Sawyer in 1986, but Calaway states that Sawyer lacked commitment and relayed limited knowledge of wrestling. So after departing from Sawyer, Calaway took a “learn as you go” approach and venture out into the wrestling world.

On June 26, 1987, Calaway had his debut match with World Class Championship Wrestling (WCCW) against Bruiser Brody. In a stroke of fate, Percival “Percy” Pringle III accompanied Calaway to the ring—the man who would later become Paul Bearer and manage The Undertaker for much of his WWE career.

In 1989, Calaway was reintroduced as The Master of Pain in Continental Wrestling Association (CWA) and managed by Dutch Mantel. Calaway wrestled then Heavyweight Champion Jerry Lawler in an impromptu match. Though The Master of Pain dominated the match, Dutch Mantel called the monster off. Lawler agreed to an official title match. The Master of Pain dominated again and won his first professional wrestling championship. Three weeks later, Lawler won the title back by becoming the first person to pin The Master of Pain.

World Championship Wrestling

Calaway joined WCW in 1989 under the new gimmick of “Mean” Mark Callous—a name that Terry Funk created. Callous was presented as a dark and nasty character. He mostly wore black, claiming that he had an affinity for snakes and Ozzy Osbourne music. Callous partnered with Dan Spivey to replace the injured Sid Vicious in the tag-team The Skyscrapers. The duo attacked the mega-popular The Road Warriors and obtained a match. However, days before the event, Dan Spivey left WCW. Callous and a masked partner lost to The Road Warriors.

Callous struck out on his own in singles competition after and joined Paul E. Dangerously. Callous defeated Ace Steel and Brian Pillman while Paul E. managed him.

Reportedly, Ole Anderson told Calaway that he was doomed in the professional wrestling world, and he believed that fans would never pay money to see Calaway as the main draw. Nevertheless, with a legitimate hip injury, Calaway pressed on and wrestled Lex Luger at The Great American Bash. He lost the match, but his primary objective was to perform regardless of injury because he knew that Vince McMahon was watching.

At the insistence of Bruce Prichard, McMahon met with Calaway to discuss a possible future in the, then, WWF. The meeting turned positive results, and Calaway gave his notice to WCW. He defeated Dave Johnson in his final WCW match on September 7.

Undertaker in WWE as “Mean” Mark Callous

World Wrestling Entertainment

Calaway signed with the WWF in 1990 and made his debut that year at a taping of Superstars. His official on-camera debut as The Undertaker came at Survivor Series as the mystery member of Ted DiBiase’s Million Dollar Team. One minute into the match, The Undertaker eliminated Koko B. Ware. He later eliminated Dusty Rhodes. He was eventually eliminated via count-out, but DiBiase went on to win the match for the team.

Throughout 1990 and part of 1991, The Undertaker squashed every opponent put in front of him—most of them being jobbers with the sole purpose of making ‘Taker look menacing. He switched managers from Brother Love to Paul Bearer in 1991. Bearer would carry an urn with them and claim the object could restore The Undertaker’s power if he were bested.

The Undertaker’s first real feud in the WWF came against “Superfly” Jimmy Snuka. The two squared off at WrestleMania VII in a match that saw The Undertaker quickly defeat Snuka. Shortly after disposing of Snuka, Undertaker began a feud with The Ultimate Warrior. The feud with Warrior culminated in the first-ever Body Bag Match, which Warrior won.

At Survivor Series 1991, The Undertaker defeated Hulk Hogan to become the World Heavyweight Champion. The victory saw Calaway become the youngest—at the time—Heavyweight Champion in WWF’s history. However, the record would only last until 1993, when Yokozuna took that honour. 

Six days after becoming WWF Champion, The Undertaker and Hogan had a rematch that saw ‘Taker lose the belt. Despite two matches, and two outcomes, both were deemed controversial, and WWF President Jack Tunney vacated the World Title. Ric Flair later won the title when he became the winner of the 1992 Royal Rumble—the only time the Rumble has decided the holder of a vacant Heavyweight Championship.

To allow time off to nurse a back injury, The Undertaker was shoved into a casket by Yokozuna and a host of others at the 1994 Royal Rumble in a Heavyweight Title match. A video feed inside the casket was shown to signify Undertaker’s spirit and eventual return. The Undertaker was out of action for seven months.

Ted DiBiase reintroduced The Undertaker after WrestleMania X, but with one problem—it wasn’t The Undertaker. Instead, the real Undertaker would return and feud with the imposter, dubbed The Underfaker by fans. Taker would assume the Deadman persona and change his colours from black and grey to black and purple. He defeated The Underfaker in a casket match at SummerSlam.

The Undertaker held several character variations throughout his WWF/E run, such as the Deadman, the Lord of Darkness, the American Bad Ass, the leader of the sinister group the Ministry of Darkness, Big Evil, and eventually returned to the Deadman to finish his active wrestling career.

Famous Matches

In Your House 18: Bad Blood – The Undertaker vs. Shawn Michaels

The first-ever Hell in a Cell match took place between The Undertaker and Shawn Michaels at Bad Blood in 1997 for the Heavyweight Championship. 

A long and gruelling match between two top performers in the company, ‘Taker and Michaels, tore the house down and left a lasting image. Michaels famously fell from the cell but still emerged victorious to retain his Championship when the debuting Kane—Undertaker’s long-lost brother—interfered and attacked Undertaker.

King of the Ring 1998 – The Undertaker vs. Mankind

While not the first Hell in a Cell ever, this one was certainly the most memorable.

 The Undertaker and Mankind had a hellacious rivalry that featured many barbaric matches. But, perhaps, none more extreme than this bought. The Undertaker demolished Mankind. He threw Mankind off the top of the cell through the announce tables, then later sent Mankind through the cell’s roof to the mat with a Choke Slam. Undertaker won the match, and the two gave the wrestling world one of the most brutal and classic contests of all time.

WrestleMania XXV – The Undertaker vs. Shawn Michaels

‘Taker had many great feuds and opponents throughout his career, but none pushed his abilities as an athlete quite like Shawn Michaels. 

If I were to make a Top 10 Undertaker matches list, matches against Shawn Michaels would occupy at least three spots—the two were just that good together. WrestleMania 25 is seen as the top candidate by many to the claim of Undertaker’s best match. The two went back and forth in a stellar, knockdown, drag-out brawl filled with high spots, intensity, drama, and nerve-wracking moments. The Undertaker won the match, but none one won more than the fans.

The Undertaker’s Wrestling Style

The Undertaker was a behemoth of a man and wrestled a style that mixed the big man technique with a dash of high-flying and technical ring work. 

While The Undertaker is mostly known for his physicality and brutal methods, the Deadman could lock up with the best technical wrestlers in the world. 

The Phenom wasn’t averse to climbing the top rope, or even literally walking the ropes, either—and he was seen many times vaulting himself over the top rope from inside the ring to crash onto his opponents. The Undertaker’s style was varied and clinical—the mark of a true talent.

Not many in wrestling can lay claim to accomplishments like ‘Taker can. An overall 7 time World Champion in WWE and holder of multiple other titles, The Undertaker saw success throughout his entire tenure with the company and cemented himself as one of the most memorable and enjoyable wrestlers of all time. 

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