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5 Most Ridiculous Things The Undertaker Has Done in His Career

Published 02/22/2022, 2:45 PM EST

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The Undertaker is perhaps the greatest performer in WWE history. The Phenom is a legendary character that has captivated the WWE Universe for years. Moreover, The Undertaker is a multi-time World Champion in WWE and has a long list of accolades.

For instance, The Undertaker has won the Royal Rumble match, and he has headlined WrestleMania several times. The Undertaker holds the greatest winning streak in WrestleMania history, as he went 21-0 at the showcase of the immortals.

The future Hall of Famer is an absolute legend in the wrestling industry. Moreover, The Undertaker made sure that his character stayed relevant for over three decades. People are still as excited to see The Deadman as they were when he came into WWE. However, as iconic as The Undertaker is, he also has been part of some insane storylines.

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When The Undertaker Hung Big Boss Man

WWE was not always PG, and The Undertaker’s character built its dark history in this era. One of the most disturbing spots in The Phenom’s career was when he hung Big Boss Man by his neck.

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This happened at WrestleMania XV, and it is obvious that it was staged, but the visual is enough to horrify anyone.

The Deadman sacrifices Stone Cold Steve Austin and Stephanie McMahon

The late 1990s were a great and confusing time to be a wrestling fan. In 1998, The Undertaker had turned heel and was feuding with Stone Cold Steve Austin. At one point in their feud, The Undertaker crucified Steve Austin on his symbol with the help of his druids.

The Legendary Career of The Undertaker Comes Full Circle With His Hall Of Fame Induction

It looks like WWE liked the idea of The Deadman sacrificing people, so in 1999 he did so again with Stephanie McMahon.

The storyline here was that The Undertaker was to first marry Stephanie and then sacrifice her to the dark forces. The Monday Night Wars were clearly a factor here.

When The Phenom’s fashion sense took a hit

For most of his career, The Undertaker has looked the part of a deadman with him clad in black. But that was not the case at Survivor Series 2000.

It is safe to say that The Phenom never wore those hilarious pants on TV again. It makes one wonder if he came up with those or were they given to him.

The Undertaker drowns Paul Bearer in concrete

The Undertaker has come forward to pay tribute to the late Paul Bearer many times. Bearer was a major part of The Undertaker’s character and he helped Undertaker’s character take a whole new mystique. But storyline-wise, the two were not always on good terms. For instance, when The Undertaker drowned Paul in concrete.

The Undertaker took his concept of burying alive to the next level here.

The Phenom throws Rikishi and Mankind off Hell in a Cell

The infamous spot involving mankind and The Undertaker will always be one of the craziest things to have ever happened in WWE. Mick Foley deserves our eternal respect for pulling this spot off.

At King of the Ring 1998 premium live event, The Undertaker threw Mankind off the top of the Hell in a Cell structure. He fell through the announce table.

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Moreover, it is not only mankind who was thrown off the cell by The Deadman. Rikishi also suffered the same fate at the hands of The Phenom.

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No matter what, The Undertaker remains one of the most beloved characters in WWE history. WWE will deservedly induct him amongst the other legends in the WWE Hall of Fame.

Watch this story: Most Memorable Moments of WWE Survivor Series

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Written by:

Tanmay Puri

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Tanmay is a WWE writer at EssentiallySports. He holds a Master’s degree in philosophy from the University of Delhi. He is a lifelong WWE fan and has been watching it for over 20 years.
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