When did WWE start acknowledging The Undertaker’s winning streak?
Despite lasting 21 WrestleManias across 23 years (The Undertaker missed WrestleMania in 1994 and 2000 through injury), the streak only really came to be a thing in the mid to late 2000s.
Prior to that, ‘Taker’s run was rarely played into storylines at WrestleMania despite his impressive streak of wins, likely because the streak was never intended to be a thing from the outset.
The winning run came to be more because it was The Undertaker, a mythical and supernatural being who was near-impossible to defeat at the best of times and normally won his feuds. Winning was just part of the character.
Feuds also often ended at Mania in the early years of his career meaning the odds of him losing was quite low often.
His opening decade came across a wide range of opponents
His opening decade of destruction at “The Showcase of the Immortals” featured a wide collection of victories. His opening two Manias matches came against two undisputed legends of the industry, Jimmy “Superfly” Snuka and Jake “The Snake” Roberts.
This strong start was largely tempered with the following two, with midcard victories over Giant Gonzales and King Kong Buddy.
The match with Gonzales was particularly tragic if not comical, given the 7’ 7” Argentinian (tallest in wrestling history) could not wrestle a lick and his lack of hulking physique meant he wore a full body suit that featured airbrushed muscles with bushy hair attached.
Wins over “monsters” were also a feature of much of The Undertaker’s early career, as a supposed unbeatable force entered the WWE and targeted Taker. There was even a fake Undertaker at one point. The Great Khali in mid 2000s was a later case of this.
The quality of both opponents and matches improved from here for the most part, with victories over Diesel (Kevin Nash), Sycho Sid and Kane at WrestleMania 12 through 14.
The win over Sid gave The Deadman his first WWE Championship for 5 years, while his first ever match-up with Kane was the culmination of the first chapter of their brotherly bond that would last for the remainder of their careers.
A largely forgettable Hell in a Cell win over the Big Boss Man came at WrestleMania 19. This was the first Cell match at ‘Mania, a rather odd selection given it was a midcard match and the cell was a speciality match saved for major blow-offs during this time. An example of the wackier booking decisions in the Attitude Era.
The “American Badass” version of The Undertaker battled both Triple H and Ric Flair
Having missed WrestleMania 2000, Taker returned as the “American Badass”, a far more humanistic version of his character and more like the real-life Mark Callaway. It changed the direction of his feuds, as promos became far more commonplace.
He promised to make his opponents “famous” during this period and the first up to the plate was Triple H. In what was the absolute zenith of the Attitude Era and arguably its last night, the two icons put on a classic at WrestleMania 17.
In what was only his second ‘Mania and first since returning to the WWE, Ric Flair was next to fall the following year. It was after this bout that the first reference to the streak was made as Taker put up all 10 fingers, signalling his now 10-0 record.
A throwback to the monster battles of a decade prior came in 2003 as he defeated The Big Show and A-Train in a meaningless handicap match. This was his final Mania match before returning to The Deadman/The Phenom gimmick.
The return to his old character coincided with a greater emphasis on the streak
This return actually came at WrestleMania 20, as he defeated Kane for a second time – his brother had buried him alive at Survivor Series 2003.
From here, the streak became part of storylines at WrestleMania, first with Randy Orton. In his run as the “Legend Killer” he attempted and failed to end the legendary streak in 2005.
However, now attempting to end the streak became a yearly mission for someone and made it a co-main event of sorts. Mark Henry was defeated at WrestleMania 22 before The Undertaker turned his attentions back to the World Title picture.
Victories came over rising stars Batista and Edge at 23 and 24, the first after winning his first Royal Rumble and the second in his first Mania main event for well over a decade. His defeat of Batista meant he had beaten all four members of Evolution at Mania.
These two World Heavyweight Titles were added to his WWE Title win over Sycho Sid. Funnily he never entered Mania as champion, perhaps because it was too obvious he would win and a title change was always fun for fans.
A four-part series with D-Generation X is up there with the best in event history
The Undertaker then moved from rising stars to veterans like himself, with a four-part series with D-Generation X, Shawn Michaels and Triple H. His two wins over the Heartbreak Kid are considered amongst the best matches in WrestleMania history.
The second of these matches was the main event of WrestleMania 26 and its premise centered around “Career vs Streak” such was Michaels’ obsession with ending the streak.
The Phenom and The Game then met 10 years after their first Mania match-up, in two matches to rival those with HBK. Two more wins were added to the Streak, the second inside Hell in a Cell with Michaels as guest referee in a match billed “End of an Era.”
CM Punk was next upto to try his luck. He was given the bout after being booked to lose his WWE title to The Rock so he could face John Cena for a second year in a row. Decisions like this ultimately led to Punk leaving WWE the following year, and he also suffered defeat.
By this stage, the streak had taken on a life of its own and was deemed a near-bigger honour than winning the WWE title, and it was presumed never to be broken.
The Streak was broken in 2014 by Brock Lesnar, a historic rival of The Deadman
That was until Vince McMahon decided another “Paul Heyman Guy” Brock Lesnar would be the “1 in 21-1”. This was due to his desire to present Lesnar as an unstoppable force – his first two years upon returning in 2012 were a mixed bag it must be said.
Lesnar was also seen as one of the few credible options to ever end the streak given his legitimacy as a UFC Heavyweight Champion. Still, it seemed slightly unnecessary. Did Lesnar need the streak to challenge for the WWE title? Did he need the aura boost that much?
Questions have been asked by fans, pundits and wrestlers alike
Other questions have been asked. Should someone else have been the one to beat him? Not that it stopped them from becoming multiple time champions, but any of Orton, Batista, Edge or Punk winning would have been more impactful arguably.
Should the streak have been beaten? Most will say no including Jim Ross, who said the Streak was a unique selling point, and Randy Orton, who viewed The Undertaker and WrestleMania as one.
Should he have retired when the streak was ended? By 2014, The Undertaker was 49 and only competing yearly at Mania. He was also concussed in the bout with Lesnar.
The post-Streak matches were of lower quality but he retired on a high
The quality of his matches dipped following the end of the streak with few exceptions.
He had five more Manias before retiring – wins over Bray Wyatt (another who could have done with being the one to end the streak), Shane McMahon (inside Hell in a Cell) and a squash victory over John Cena (10 years prior, it would have been the marquee match).
He suffered a second loss to Roman Reigns in 2017 at WrestleMania 33, as the company further looked to establish Reigns as the face of the company. It all felt a bit unnecessary, and the impact was diminished with the streak already over.
The Undertaker finally retired after WrestleMania 36 in 2020 after a cinematic “Boneyard match” with AJ Styles. It was widely praised and well-received and a nice way for The Deadman to close out his career.
His Mania record ended at 25-2. The most Mania matches, the most Mania wins and the best Mania record. But it is hard not to question whether the streak should have remained intact. It is a debate that will rage on for decades to come.