In the world of professional wrestling, few names carry the weight and mystique of The Undertaker. For over three decades, The Undertaker, real name Mark Calaway, has been one of WWE’s most iconic figures. His dark, supernatural persona, unmatched longevity, and legendary performances have made him a true cornerstone of sports entertainment. From his debut in the early 1990s to his retirement in 2020, The Undertaker’s journey has been a story of reinvention, resilience, and unforgettable moments that have defined eras in wrestling.
OddsMonkey, the matched betting service for UK bettors, collated this deep dive into the Undertaker’s journey through wrestling history.
The Mysterious Debut
The Undertaker made his WWE (then WWF) debut at the 1990 Survivor Series, an event that would go down in wrestling history. Introduced by “Million Dollar Man” Ted DiBiase as the mystery partner for his team, The Undertaker was unlike anything fans had seen before. Standing at 6-foot-10 and draped in dark, Western-inspired attire, he struck an imposing figure as he slowly made his way to the ring, accompanied by eerie funeral music. His piercing gaze and methodical style left the audience in awe, and it was clear that the WWE had something special on their hands.
From the outset, The Undertaker was portrayed as an unstoppable force. With his manager Paul Bearer at his side, clutching the infamous urn that seemed to give him his supernatural power, The Undertaker quickly became a feared competitor. His gimmick was that of a dead man, a seemingly immortal being who could absorb incredible amounts of punishment and still rise again, often by dramatically sitting up after what seemed like a certain defeat. It was a character that perfectly blended horror movie vibes with the theatricality of wrestling.
Dominating the WWE
Throughout the 1990s, The Undertaker became one of WWE’s most popular and enduring superstars. His character went beyond mere gimmick, as he displayed an incredible in-ring ability that allowed him to have memorable matches with nearly every major star of the era. He became a staple of the company’s biggest events, and his presence in the ring was enough to turn any match into a must-see spectacle.
One of his earliest major feuds was against Jake “The Snake” Roberts, culminating in a match at WrestleMania VIII, where The Undertaker’s winning streak at WrestleMania began. Little did fans know that this would turn into one of the most famous streaks in wrestling history, eventually reaching 21 consecutive victories at WrestleMania before finally ending in 2014.
In the mid-90s, The Undertaker found himself in some of the most intense rivalries in wrestling, including unforgettable battles with Mankind (Mick Foley). Their 1998 Hell in a Cell match at King of the Ring became the stuff of legend. The moment when The Undertaker threw Mankind off the top of the cell, sending him crashing through the announcer's table below, remains one of the most iconic images in wrestling history. It was a match that showcased the extreme lengths both men were willing to go to entertain the fans, and it solidified The Undertaker’s reputation as a true master of the Hell in a Cell format.
Reinvention and The Streak: The 2000s and Beyond
As the 1990s ended and the 2000s began, The Undertaker reinvented himself, proving his adaptability and longevity. In 2000, he adopted the “American Badass” persona, ditching the supernatural elements for a more grounded, biker-inspired character. Riding a motorcycle to the ring to the sound of Kid Rock or Limp Bizkit, The Undertaker showed a different side of himself, one that emphasised his toughness and loyalty to the wrestling business.
This reinvention allowed him to connect with fans in a new way, but by 2004, he returned to his roots, bringing back the Deadman persona that fans had grown to love. The early 2000s also saw the rise of The Undertaker’s most famous achievement: The Streak. His undefeated record at WrestleMania became a central part of WWE’s storytelling, and each year, fans would eagerly anticipate whether anyone could finally break it.
Matches against superstars like Triple H, Shawn Michaels, and Batista became instant classics, with The Undertaker delivering some of the best performances of his career. His bouts with Shawn Michaels at WrestleMania 25 and 26 are often regarded as some of the greatest wrestling matches ever.
The Streak Ends: WrestleMania 30 and the Last Ride
WrestleMania 30 in 2014 marked a turning point in The Undertaker’s career as he faced off against Brock Lesnar. The match itself was far from The Undertaker’s best performance, with rumours that he suffered a concussion early on, but the outcome shocked the world. Brock Lesnar defeated The Undertaker, ending The Streak at 21-1. The silence that fell over the New Orleans crowd when the referee counted to three was unlike anything in wrestling history. The Streak had become such a part of The Undertaker’s legacy that its end felt like the end of an era in wrestling.
But even after The Streak ended, The Undertaker continued to be a key part of WWE’s biggest events. He faced stars like Bray Wyatt, Roman Reigns, and John Cena in matches that often carried a sense of finality. Each appearance felt like it could be his last, and fans savoured every moment of his entrances and the iconic bell toll that signalled his arrival.
Retirement: A Legendary Career Comes to an End
After years of speculation about when he would finally hang up his boots, The Undertaker announced his retirement in 2020. His last match came at WrestleMania 36, where he faced AJ Styles in a cinematic Boneyard Match, a unique blend of action and drama that felt like a fitting send-off for such a legendary character. The match was praised for its creativity, and it allowed The Undertaker to go out on a high note, even as the world was dealing with the challenges of the COVID-19 pandemic.
Later in 2020, WWE honoured him with a special Final Farewell segment at Survivor Series, marking 30 years since his debut. It was an emotional moment for fans, colleagues, and The Undertaker himself as he said goodbye to the character that had defined his life for three decades.
