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The Undertaker is one of the greatest legends to have ever walked through the hallowed halls of the WWE. During his 30-year tenure with the company, The Phenom managed to maintain the mystique of his unique character.
He held the same power over the audience from the first day that he walked out to the ring, to the last day - his Final Farewell at Survivor Series 2020. A man who left his mark on the WWE Universe and the entire wrestling world, The Undertaker is undoubtedly one of those performers who will be remembered for as long as wrestling lasts.
Throughout his career, The Undertaker has rarely, if ever, broken character. In fact, he has always taken pride in maintaining the gimmick, be it inside or outside the ring. Wrestlers often tried their best to get him to break character by playing pranks.
However, those rare moments do exist where The Undertaker broke character. The following are the times when even The Deadman couldn't maintain his facade.
#5 The Undertaker's Last Ride documentary
The Undertaker is not someone who broke character for a long period of time at any point in his career. However, heading towards the end of his career, The Undertaker was filmed in a documentary. A film crew followed him around in order to document the final few years of the beloved wrestling legend.
Undertaker: The Last Ride documentary was one that allowed fans to see The Deadman speak with a frankness that no one ever thought to see from him. In an exclusive view of how he ended his wrestling journey, fans saw The Undertaker end his wrestling career on his own terms.
The legend didn't maintain his character for the interviews and it let fans see Mark Calaway, the man behind The Undertaker. For perhaps the first and last time, they could say that they got a peek behind the curtain that the man maintained for the best part of 30 years.
#4 Elimination Chamber 2010: The Undertaker suffers burns
There are very few wrestlers who can remain cool under fire like The Undertaker. The Deadman is known for his gimmick of being the guardian of hell, who has sent more than one opponent to their resting place.
However, one time, the gimmick caught up with The Deadman in the most unexpected way. While he was making his way out to the ring, during the 2010 Elimination Chamber pay-per-view, the pyro went wrong and his clothes caught on fire a bit.
He had to stagger and break his usual slow march down to the ring by running a bit. To the casual fans, it would perhaps not make a difference, but for fans of The Undertaker, it was obvious something was wrong. The Phenom had suffered burns to his body and he shed his coat really fast.
He had to wait a long time as well before it was his turn to enter the ring. He emptied bottles of water over himself to control the pain. He paced his pod throughout like a tiger and it turned out that he had sustained some legitimate burns.
Despite breaking character for a while, The Undertaker went back to doing what he does best. He maintained character for the rest of the match and did whatever it took to remain convincing until the match ended.
#3 WrestleMania 33: The Undertaker kisses Michelle McCool
For a lot of his fans, it seemed like WrestleMania 33 would be the final time that The Undertaker would compete inside a wrestling ring. At the event, he faced Roman Reigns following a long drawn-out feud.
The match was intense and saw Roman Reigns and The Undertaker battle in an incredibly brutal contest. Going into the match, The Deadman already expected the match to be his last. He was treating the contest as his farewell to the fans. Unfortunately, thanks to injuries he suffered over the course of his long career, heading into the match, he was in a great deal of pain.
Still, Roman Reigns defeated The Undertaker in their match and he tried to put on the best match that he could. After the match, he placed his hat, coat, and gloves in the middle of the ring. He then broke character and went to the ringside area to kiss his wife, Michelle McCool. It was something no fan had ever seen him do before.
Eventually, The Undertaker would return, but the moment remains an emotional reminder of the man behind the character.
#2 RAW 2008: The Undertaker bids Ric Flair farewell
The Undertaker is a legend himself, but sometimes, he has broken character to pay respect to other legends.
Ric Flair is one of the biggest legends to ever step foot into a wrestling ring. Throughout the early 80s and 90s, Flair battled across the world as one of the top names.
Following WrestleMania 24, Ric Flair finally decided to retire from the ring. His retirement was an immense moment for the wrestling world. Flair's friends and old opponents all made their way out to the ring to say their final farewells. However, one of the most shocking participants at the ceremony was none other than The Undertaker.
He made his way out to the ring in a post-show segment. He hit his classic pose for the legend and then stood up to shake his hand and hug him. It was the first time that The Undertaker allowed a different side of him to show on camera.
The breaking of his character only added to the gravitas of the situation, and brought The Nature Boy to tears. The moment is a testament to the respect that The Undertaker had for the retiring legend.
#1 WrestleMania 28: The Undertaker signals the end of an era
The Undertaker had some of the best matches of his career at the 25th, 26th, 27th, and 28th editions of WrestleMania. There, he battled Shawn Michaels in the first two events, and Triple H in the second two.
The Deadman looks back at the storylines surrounding his matches and the matches themselves with a lot of fondness.
In possibly the greatest wrestling story ever told, The Undertaker faced Triple H for the second time in two years at WrestleMania 28. The Deadman had already beaten and retired Shawn Michaels in the 25th and 26th editions of the event. He had defeated Triple H the year before but had not been able to walk out of the event.
All three men were involved in the story. The Undertaker faced Triple H in the match to end an era. It took place inside the Hell in a Cell structure, and Shawn Michaels was a guest referee. All three men told a story as the two battled each other and Michaels could be seen being torn between helping his best friend and calling the match down the middle.
In the end, he counted the pinfall and The Undertaker defeated Triple H.
After the match, in a rare moment, all three men broke character. They supported each other as they walked out of the ring and stood in the entryway to turn back and look at the audience as they shared a hug. It will always remain one of the most emotional stories WWE has ever told.
