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Pro wrestling fans were able to see a very different side of The Undertaker recently, as The Last Ride documentary on WWE Network provided us all an in-depth journey of the past three years of his WWE in-ring career. At the conclusion of the documentary, The Phenom announced that he does not have any plans on returning to the ring, following his final match at WrestleMania 36 against AJ Styles.
As many of his matches were touted, the Boneyard Match against Styles was positively acclaimed by many who watched the unprecedented two-day event. This match further cemented that The Undertaker has the most impressive WrestleMania presence in WWE history. However, there are some of his matches that should have been different than what was scheduled.
The Undertaker's WrestleMania journey started in 1991. From 1991-2013, he went on a 22-match winning streak. Additionally, he only was absent from two WrestleMania events, which were WrestleMania X in 1994 and WrestleMania 16 in 2000. Throughout this streak, he racked up wins against names who are now in the WWE Hall of Fame, which include Jimmy Snuka, Jake Roberts, Diesel, Big Boss Man, Ric Flair, Mark Henry, Batista, Edge, and Shawn Michaels. In addition, he added former WWE Champions CM Punk, Kane, and The Big Show to his list.
Following the end of the streak at WrestleMania 30, Undertaker has competed in five out of the past six events of the series, defeating Bray Wyatt, Shane McMahon, John Cena, and AJ Styles. He also fell victim to his second-ever WrestleMania loss, against Roman Reigns, at WrestleMania 33 in Orlando, Florida. This was thought to be the end of The Deadman's career from his post-match actions, but as seen in the documentary, there was a void to be filled. He wanted to leave with feeling satisfied with his last match, and AJ Styles did just that. While his match with Styles was positively critiqued overall, not every WrestleMania match was.
Here are 5 WrestleMania matches involving The Undertaker that should have been different.
#5. WrestleMania 9 vs Giant Gonzalez
Should have wrestled: Yokozuna
In WCW, he was known as El Gigante, and was a babyface engaged in top-level feuds against Ric Flair, Big Van Vader, Sid Vicious, and the One Man Gang. With his enormous size, Vince McMahon apparently saw money in him, and he was brought into the company as an intimidating heel in 1993. The WWE creative team were clearly holding nothing back on propelling him to be a top name, as he gained a featured spot on WrestleMania IX against The Undertaker less than two months after debuting.
This match has been widely known to be the worst match of The Undertaker's WrestleMania series. Not only did The Undertaker have to work around the physical limitations of Gonzalez, but the match was won by disqualification. Clearly WWE still wanted to protect the character of Giant Gonzalez and extend the feud, but it was a bad call, especially retrospectively. The rivalry concluded at SummerSlam the following year in a "Rest in Peace" match, and Gonzalez left the WWE shortly after.
While it would require an entire reworking of nearly every storyline leading up to WrestleMania IX, a match between 'Taker and Yokozuna would have been a much better attraction. In fact, according to The Undertaker, this was the match he wanted before Vince McMahon placed him in the program with Gonzalez.
However, instead, we got Giant Gonzalez smothering Undertaker with choloform and Hullk Hogan ending up at the end of the night WWF Champion.
#4. WrestleMania 7 vs. Jimmy Snuka
Should have wrestled: Andre the Giant
In 1991, The Undertaker competed in his first WrestleMania match, squashing Jimmy Snuka in less than five minutes. Just four months after his Survivor Series pay-per-view debut, the mission was clear: to continue making Undertaker look like a dominant giant, plowing through his opponents to further intimidate future competitors. While this match accomplished just that, it also missed out on an opportunity that WWE fans never had a chance to see.
WrestleMania VII would have been a great opportunity for the colossal match-up between The Undertaker and Andre the Giant. There are a few match-ups that may forever live in the dreams of WWE fans, and this is indeed one of them. Andre the Giant putting The Undertaker over at WrestleMania VII would have catapulted Undertaker's career even higher than it already was, and fulfilled the "What If" that will now have no other choice to be relegated to live in fantasy.
Andre even expressed the desire at one time to have a match against him, as Undertaker claimed during a 2018 interview with Pastor Ed Young.
#3. WrestleMania 15 vs. Big Boss Man
Should have wrestled: Stone Cold Steve Austin and The Rock
During this time in the The Undertaker's career, he was a menacing heel trying to dominate the company during his WWE Championship feud with Steve Austin. In the quest absolute dominance in the company, Undertaker turned heel and made a mission to take control of WWE from Vince McMahon. Despite being in a bitter rivalry with McMahon, Austin found it in his heart to protect his boss and rival due to tndertaker's tormenting of Vince's daughter, Stephanie. The feud between Undertaker and Vince led to a Hell in a Cell match against The Bossman at WrestleMania XV.
Wait. What?
This match made little sense in the overall storyline arc. Although Big Bossman was generally a notable name, a WrestleMania match against Undertaker was just not very fitting at this point of his career. Both Bossman and Undertaker were heels, so the fans were forced to pick from the lesser of two evils, esentially.
Additionally, the match was clearly going to be in The Undertaker's favor, and it did not do much to help his character. They attempted to make his character even more devious by literally hanging Bossman by a noose, but it came off more hokey than devious.
At the time, Steve Austin was occupied in a match against The Rock at WrestleMania. However, Undertaker being inserted into that match, and winning the title, would have been a perfect extension of the stories being told at the time.
#2. WrestleMania 19 vs The Big Show and A-Train
Should have wrestled: singles match against Big Show
By the time WrestleMania XIX rolled around, Undertaker transitioned out of his "Big Evil" heel character, and back into a babyface. At the start of 2003, Undertaker commenced a feud with both A-Train (now head NXT trainer Matt Bloom) and Big Show, defeating Train on the January 23, 2003 episode of SmackDown. Subsequently, he also defeated Big Show on the February 23, 2003 No Way Out pay-per-view.
A-Train competed against Undertaker once again on the March 6 episode of SmackDown, and won by disqualification. On the previous episode, Big Show and A-Train gang attacked Undertaker, which led to Nathan Jones making the save.
This angle was supposed to lead to a tag team match with Undertaker & Nathan Jones against Big Show & A-Train. That didn't happen. WWE executives felt that Jones' in-ring work was not up to par and, as a result, the match was turned into a handicap match, although Jones did eventually get involved at the end of the bout.
The whole angle was odd, and appeared to be for the purposes of giving the new big man a spotlight right from the start. Instead, Undertaker was placed in a handicap match that did not fit the overall quality of most of his bouts on the big stage. While the fact the Undertaker competed by himself was a good thing, the angle was not WrestleMania worthy, and even a single match against the Big Show would have looked better on paper.
#1. WrestleMania 32 vs. Shane McMahon
Should have wrestled: Brock Lesnar
The Undertaker and Shane McMahon certainly had a history, dating back to their Corporate Ministry alliance, but the storyline leading to WrestleMania 32 was just odd.
Shane made a thunderous return by interrupting the Stephanie McMahon appreciation segment, as Vince was awarding her with the "Vincent J. McMahon Legacy of Excellence Award" in honor of his late father. Shane came in to stop the Triple H/Stephanie McMahon power trip that was running roughshod, and wanted control of Raw to return a favor he did for his father years prior. Vince agreed, as long as Shane agreed to the stipulation of Vince choosing a person for him to defeat, as well as a place for the match. Vince chose The Undertaker at WrestleMania, and the match was Hell in a Cell.
While the match was not terrible, it also did not live up to par with the other Undertaker matches at WrestleMania. Undertaker won the match, which the stipulation of his career was later added, and Shane was left without control of Raw. However, to make the match even more irrelevant, Vince would go ahead and give Shane control over Raw the next night, anyway.
Prior to this match, Undertaker had not competed in the ring for nearly five months, as he last teamed up with Kane to defeat the Wyatt Family (Bray Wyatt and Luke Harper) at Survivor Series. Prior to that, he was defeated once again by Brock Lesnar at the 2015 Hell in a Cell pay-per-view, so a rematch at WrestleMania 32 against Lesnar to redeem his streak ending would have been much better than being inserted into an odd storyline involved Vince and Shane McMahon.
