7. “Where to Stephanie?”
It was a toss up whether to have “Where to Stephanie?” or “Buckle up Teddy!” on this list. In the end, we decided on the former. The Undertaker appearing in the front seat of Stephanie McMahon’s limousine remains an iconic moment and one of the most quotable moments of the Attitude Era. It continues to be referenced to this day with Big Swole giving a nod to the segment on AEW.
6. A Royal Victory
After 17 years in WWE, there were few things The Undertaker had left to accomplish. One thing left on that list was to win the Royal Rumble. This match did as much for the stipulation as it did for ‘The Deadman’ himself. Having one of the most revered names in wrestling history on the list of past winners helped to build the prestige of the match even further.
On top of that, this performance was impeccable. The 2007 Royal Rumble was one of the best in the history of the stipulation and a good portion of that is due to The Undertaker’s mini-match with Shawn Michaels. They were the final two men left in the match and they battled for the final spot. Eventually, Michaels missed a Superkick and was dumped to the outside.
5. First Time to the Mountaintop
The Undertaker’s first reign as WWE Champion lasted only six days. While the reign was nothing to speak of, the moment of winning the title for the first time remains. At the 1991 Survivor Series, one year after his debut, The Undertaker defeated Hulk Hogan to win the WWE Championship.
It was a famous moment as the title seldom changed hands in such a manner. Ric Flair had placed a chair in the ring for ‘The Phenom’ to Tombstone Hogan on top of. Hogan claimed to suffer a neck injury from the move despite his head missing the chair by about four inches.
4. The Deadman Returns
Many have feelings of nostalgia for the American Badass version of The Undertaker character. While the gimmick had its fans, people went crazy when the Deadman returned at WrestleMania XX. Kane had buried his brother the previous year and now he had returned for his revenge.
Accompanied by Paul Bearer, The Undertaker provided one of the greatest entrances in WWE history. Flanked by druids carrying torches, he rejoined WWE the same was he entered in 1990.
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