Corrigan’s Corner: Undertaker’s 25 Craziest Moments

Sunday marks 25 years since the Undertaker entered WWE, and the wrestling world has never been the same. The Deadman started as a headliner, and by God, he’s remained that way for a quarter century. Although he’s worked a reduced schedule over the past five years, the Phenom still delivers that big-time fight atmosphere, maintaining a perpetual edge to his character while bringing fans back to the Attitude Era, New Generation, and end of Hulkamania.

In honor of Undertaker’s silver anniversary, here are the 25 craziest moments in his iconic career.

25) Debuting At Survivor Series

“Look at the siiiize of that hamhock!”

24) Winning The 2007 Royal Rumble

Hard to believe, but it took the Phenom 17 years to win a Rumble. He was also the first man to enter at #30 to win it. Of course, a description of the final 10 minutes between hometown boy Shawn Michaels and Undertaker can’t compare to actually watching the match. So go do it.

23) Attacking David Flair

At No Way Out 2002, then-co-owner Ric Flair prevented the Undertaker from using a FOREIGN OBJECT on The Rock, which led to The Great One scoring the victory. So Booger Red (as J.R. called him) sought revenge against the Nature Boy, demanding a match at WrestleMania X-8. Flair repeatedly refused, so Undertaker went badass bully on Arn Anderson and Naitch’s oldest son, David.

22) Royal Rumble 2006 Return

After Kurt Angle successfully defended the World Heavyweight Championship against Mark Henry, a new challenger rose from the depths of hell.

21) Returning To The Dark Side

At WrestleMania XX, “Where It All Begins…Again,” the Undertaker ditched his American Badass persona for the old gong, druids, and Paul Bearer.

20) Saving Elizabeth From Jake Roberts

This marked the Undertaker’s turn from brooding monster to heroic avenger.

19) Ladder Match With Jeff Hardy

Although the “Rainbow-Haired Warrior” wouldn’t win the WWE Championship for another six years, this battle with Big Evil showed fans, for the first time, that Hardy was a main-event player.

18) Eliminated By Maven

The dropkick heard round the world.

17) Winning The WWE Championship

There was no hanging or mystical powers used in Taker’s capturing of the WWE Championship; however, it was crazy (and maybe moreso today) that a man who debuted just one year earlier could defeat Hulk Hogan, albeit in the decline of his prime.

16) Embalming Austin

During his Satanic days in the Attitude Era, Undertaker knocked out Stone Cold, took him to a funeral home, and attempted to sacrifice him. Kane interrupts the proceedings and lunacy ensues.

15) Locking Ultimate Warrior In The Casket

Another one that seems eerie considering Warrior’s untimely death, but at the time, it was par for the course when it came to “Big Evil.”

14) Returns At Judgement Day

For weeks a video aired of children creepily chanting about Judgement Day. Of course, it seemed like a commercial for the annual May pay-per-view. Well, during the final minutes of The Rock and Triple H’s Ironman match, the video aired again, but ended with “Now Back from the Dead.”

13) SummerSlam 2009

After CM Punk survived a TLC and won back the World Heavyweight Championship from Jeff Hardy, he stood victoriously over Hardy until the lights went out. When they turned on, Punk was still standing, but Undertaker was lying between his legs.

12) The Dive At WrestleMania 25

It was a WrestleMania tradition like Rey Mysterio dressing as superheroes and J.R. busting out the John Wayne cuff links. However, during his encounter with Shawn Michaels, Part I, the Deadman appeared to be actually dead.

11) Marrying Stephanie McMahon

If only the unholy matrimony went through between the “Billion Dollar Princess” and the “Lord of Darkness.” CM Punk says it still did.

10) Undertaker vs. Underfaker

After ascending to the heavens at the Royal Rumble, Undertaker was MIA. But Ted DiBiase claimed to have not only found Taker but also purchased his services. Paul Bearer cried foul, and at SummerSlam 94, the true Phenom returned to face the “Million Dollar Man’s” imposter.

9) Burned In The Casket

When the Big Red Machine stuffed his brother in a casket and set it ablaze, fans cried out for someone to rescue Undertaker. When the flames were finally extinguished, the Phenom was nowhere to be found.

8) Pulls Diesel Through the Ring

Before Kane yanked Seth Rollins through the ring, Taker originated it during the main event of In Your House: Rage in the Cage.

7) Burying Paul Bearer

It made no sense then, and makes no sense now, but that’s why people still talk about it.

6) Resurrecting At Royal Rumble 1994

It’s goofy, campy hijinks that only the Undertaker character could pull off. When he finally does descend into the depths of Death Valley, Bray Wyatt will be left to continue the supernatural wizardy.

5) The Laugh

You know the meme.

4) Hanging The Big Boss Man

It’s highly unlikely that you’ll see WWE show this footage in the PG Era. It’s also disturbing considering Boss Man died just five years later.

3) The Streak Ends

It has eclipsed the Montreal Screwjob as the most talked about finish in the history of wrasslin’. Witnessing the ref’s hand slam the mat for a third time made my eyes pop like a Tex Avery cartoon.

2) Crucifixion On The Symbol

Symbol or cross, it doesn’t matter, Undertaker’s Ministry of Darkness crucified Stone Cold during the zenith of the Attitude Era.

1) Throwing Mankind Off The Cell

Has there ever been a visual more stitched in our minds? We’ve memorized J.R.’s call and we know the dimensions of the steel structure. The only reason this moment is more associated with Mick Foley is because he talks about it ad nauseum. If the Deadman did interviews, he’d probably admit it’s the one time he thought his opponent truly rested in peace.