The Undertaker has finally ended his legendary career, but fans still enjoy talking about his decades of contributions to the business. Vince McMahon has named Undertaker the most respected superstar in WWE history. Undertaker is mostly remembered for his hit list of classic matches and noteworthy storylines to take place on the big stage.
WWE doesn’t like to discuss everything about their most protected legends, and Undertaker is at the top of the list. The presence of social media and various wrestling platforms have led to enough stories and on-screen moments becoming skeletons in his closet. WWE likely wants fans to forget the following things about Undertaker’s career.
10 Hitting Chris Kanyon With Stiff Chair Shots
The Dark Side of the Ring episode looking in depth at Chris Kanyon’s career shined a light on an overlooked story. A controversial segment featured Kanyon appearing out of a gift box left for Undertaker and singing a Boy George song.
Undertaker delivered a stiff chair shot to Kanyon that many felt crossed a line. The segment made no sense, so Kanyon and others felt WWE was trying to make homophobic inside jokes about him that ended with Undertaker almost injuring him.
9 Threatened Vince McMahon After Montreal Screwjob
The Undertaker is considered one of the closest wrestlers to Vince McMahon after decades of work together. Even though the two share a bond, there were moments of friction between them backstage.
The Montreal Screwjob caused a lot of wrestlers to be upset at Vince for lying to one of the boys going in the ring. Undertaker was the one to knock on McMahon’s office and demand he go explain himself to Bret Hart. If not for Undertaker, Vince may not have been punched out by Bret.
8 They Made Him Job To Great Khali
WWE tried to make new wrestlers relevant by having them work with The Undertaker if their character could benefit from it. Mick Foley showed the best-case scenario, but many others couldn’t rise to the occasion in such a big spot.
The Great Khali may have been the worst instance of WWE trying to force fans into viewing someone as a big star by facing Undertaker. WWE absurdly booked Khali to dominate Undertaker for his debut segment and match to make the legend look foolish.
7 DQ Finish With Giant Gonzalez During The Streak
The Undertaker’s undefeated WrestleMania streak is one of the most respected stories in WWE history. Many of the matches from the streak were iconic bouts, but it didn’t become a special attraction until the 2000s, more than a decade into it.
The one aspect of the streak that WWE wishes they booked better was Undertaker’s WrestleMania 9 match vs Giant Gonzalez. WWE went with the DQ finish to have Undertaker win without beating Gonzalez cleanly. This ended up being for nothing as it added a dark mark on Undertaker’s future streak, and WWE gave up on Gonzalez.
6 Had Backstage Issues With CM Punk
WWE likes to paint the picture of The Undertaker being viewed as a locker room leader to help the rest of the roster. Quite a few wrestlers disliked Undertaker throughout his career, and he had backstage heat with one future legend.
CM Punk’s World Championship reign as a heel in 2009 saw Undertaker criticizing him backstage for not dressing in suits like a champion. The title run of Punk coincidentally ended with Undertaker destroying him in a glorified squash match.
5 WM 13 Title Win Was A Backup Plan
Undertaker won the WWE Championship for the first time in 1991, but he didn’t get a real reign lasting beyond a few days. This made it feel like the WrestleMania 13 victory over Sycho Sid was his crowning moment as the WWE Champion.
Undertaker received his WrestleMania main event to have the highest honor in WWE. However, there was an interesting backstory of Shawn Michaels vs Bret Hart being planned for that show’s main event. Michaels having a short retirement changed those plans to give Undertaker his moment as a backup plan.
4 Burying Paul Bearer Alive For No Reason
The Undertaker returning to the Deadman gimmick in 2004 saw Paul Bearer coming back with him to sell the character shift. Bearer managed Undertaker for about a month before getting abducted by Paul Heyman and the Dudley Boyz.
The absurd Concrete Crypt match saw Undertaker having to defeat the Dudley Boyz to prevent Heyman from burying Bearer in concrete. Undertaker won but chose to fill the crypt with Bearer still in it. WWE tried to sell it as Undertaker wanting to lose any weaknesses, but it remains a regretful moment that almost ruined his face character.
3 Embarrassing Saudi Arabia Returns
WWE striking a deal with Saudi Arabia for a couple of major events each year has financially benefited Undertaker more than most wrestlers. The desire for legendary figures from the past eras will see more profits coming in.
There were a few embarrassing moments for Undertaker on these shows that will always haunt him. Shawn Michaels came out of retirement for a horrid match teaming with Triple H against Undertaker and Kane. Another match with Goldberg saw both guys almost getting injured and showing their age in embarrassing fashion.
2 Ex-Wife Sara Becoming His Manager
One strange chapter of The Undertaker’s career saw his then-wife Sara becoming an on-screen character for a few months. WWE brought in Sara during Undertaker’s time as the American Badass when he was representing the company against The Alliance.
WCW’s Diamond Dallas Page debuted in the storyline as a mystery person stalking Sara. WWE had Undertaker bury DDP with Sara getting to pin him. Undertaker felt off having a valet at ringside and WWE ended it soon after.
1 Forcing Wrestlers Into "Wrestlers' Court"
Many stories about the old school wrestling locker room have painted the business in a horrible light. Wrestlers’ Court stands out as a horrible concept that showed the ridiculous backstage environment and how talents were allowed to cross the line.
The Undertaker was often the one coming up with instances of demanding a wrestler defend themselves against a case with the rest of the locker room watching. A lot of these stories bordered on bullying, with Melina once breaking down in tears. Undertaker is the main wrestler that should get the blame for forcing this as a “locker room leader.”