Hooked On Roundtable: Our All-Time Favourite Undertaker Moments

The Undertaker WrestleMania 30 Entrance

This piece was originally written during our ‘Undertaker Weekend’ in June 2020. We are republishing this ahead of Undertaker’s ‘Final Farewell’ at Survivor Series.

Whether he’s tearing the house down with HBK or stinking up the joint with Giant Gonzalez, The Undertaker has always been second-to-none when it comes to iconic, spine-chilling, unforgettable moments.

Within a match, during his entrance, after the final bell or even in a backstage segment, Taker’s presence leaves an impression.

So we asked the team, to commemorate our special Undertaker Weekend, to name ONE moment that stands out to them above all else.

The rules were simple: an entire match could not be selected. It has to be a particular moment – however that moment can be one that took place in an actual match.

Here’s what we selected. Let us know your own choice while sharing this article on social media!


Liam Happe: The Undertaker spent his first five years as a babyface slaying monsters and freaks in the sideshow bout of most major cards. It wasn’t until 1997-98 that he began to evolve into a member of WWE’s all-time elite, earning his first WM main event and engaging in some absolute bangers vs the Bret Harts and Shawn Michaels. And when Stone Cold Steve Austin surged past everybody and became THE guy, a major World title challenge from the Dead Man seemed inevitable.

It was UT’s desperation to regain the title and prove he, not Austin, was the king of the mountain that shone through in the main event of Summerslam 1998 at Madison Square Garden. And while the match was a little rough around the edges, it remained suitably-epic – especially when Taker showed how far he was willing to go for victory by climbing to the top rope and flying through the air to the outside, where he put the defending champ through the announcers’ table with an insane legdrop.

That highspot always stands out to me as the peak of prime Undertaker, even if the HIACs were a little crazier and the Hart battles were a little better overall.

Paul Benson: I’m going to go back to my childhood for my choice. It’s a moment when I saw for the first time that The Undertaker was more than just a methodical heel-smashing machine, that he had a personality and could be a babyface that could ‘play nice’ with others.

In the run up to Survivor Series 1993, Tatanka had his undefeated streak ended by Ludvig Borga and was put out of action by the Finn and Yokozuna.
Lex Luger and The Steiner Brothers needed a replacement for their All-Americans team to face the Foreign Fanatics at the PPV. Who would they choose? On an episode of WWF Superstars, they named their guy.

To my 11 year old mind, this was the most awesome thing ever. Undertaker stepping in as part of a team was just so cool. He had been a lone wolf his entire babyface run up to this point. The real moment that made me jump off my sofa though was the final reveal. ‘Taker put the seal on the moment by memorably opening his trench coat (ooh er!) to reveal an Old West-style American flag.

Whilst not remotely close to being the most significant moment of Undertaker’s long career. It’s one that I will always remember for making me fall in love with wrestling just that little bit more.

Jason Auld: A moment that is seared into my childhood memory is when Undertaker, during the build up to his Mania match with Ric Flair, ambushes Ric’s son David at a wrestling school. Accompanied by shakey, Blair Witch-style filming, he absolutely destroys the kid and cuts a promo to the camera whilst sat in a shower, cradling Flair’s blooded remains. It felt like an execution.

A beat down, outside of the ring that didn’t take place in the caricature world of the Hardcore division, featuring Flair’s real life son, who wasn’t a character on WWE television. It really introduced a level of brutality and viciousness to Taker’s new heel persona that he continued to stoke with a guerrilla attack on Arn Anderson, leading to his eventual win at Mania 18.

Although it’s unlikely to feature in Takers top moments it was savage, intense & unforgettable.

Marc Hemingway: Mine’s anytime he turns up somewhere unexpected. Behind the wrestler in the ring, smashing his way up THROUGH the ring… but my favourite is out of a casket, namely in the Shawn Michaels v Mankind at In Your House: Mind Games.

It was already a fantastic match but with the casket being all ‘Chekhov’s Gun’ at ringside I was on the edge of my seat every time they went near. Brilliant bit of storytelling in an already-brilliant match.

Joe Kennard: It was only a very small moment but as a kid when I first got into wrestling I was given a VHS copy of the Royal Rumble 1997. The Undertaker’s entrance in the Rumble match itself blew my mind. All the lights went to black while wrestling was still going on inside the ring!

It was like nothing I’d ever seen before and he was in no rush to make it down to the ring. Undertaker would do things at his own speed the way he wanted to and I thought that was so cool. A very small moment but it made me realise that when it came to The Undertaker, anything was possible.

Rob McNichol: I love it when people try to be different, rather than simply variations on the same things. That applies not just to wrestling, but to sport, comedy, all sorts. If you can add a level of subtlety and class, even better.

The day everyone was expecting Undertaker to come back after those shed promos that may or may not have originally been for Sting, down came Taker, doing his long entrance. And at the second he was about speak… Triple H walks to the ring. He and Taker look at each other… then slowly at the Wrestlemania sign. The whole segment is about 12 minutes, as I recall – and they never said a word.

Justin Czerwonka: I’m going to go with experiencing his entrance live at all three Wrestlemania weekends I attended. I’ve attended Wrestlemania 27, 29 and 35. There is something so different and special about seeing Taker’s entrance on the big stage. You can feel the build up to it in the crowd as they all wait to see what the entrance will bring this year.

I especially loved the Undertaker’s entrance at WM29, with the zombie-like creatures coming up from the stage. Even WM35 week, despite not appearing, everyone loved his entrance at RAW. The second Elias said: “If anyone interrupts me they’re a dead man”, the whole crowd knew what would happen.

Steve Cox: It’s so hard to pick one moment. But it’s all about the entrances for me. And I’m going back to Wrestlemania 9. That entrance, the chariot, the vulture. Yeah, it may have been the worst Wrestlemania match in history, but you know what? I still remember that entrance and love the match because of that entrance.

Ash Rose: His debut. Even as a kid, I was so intrigued to who Ted Debiase’s mystery partner was, especially as I had no clue into the inner workings of the business. Then when Undertaker made his entrance I was absolutely transfixed to the screen looking at this giant zombie no one could hurt. Even after he left the match, he was the wrestler I was telling my Dad about and I couldn’t wait to see more of him.

Chris Hatch: I’m going to go for a completely personal one, but hopefully it links to something many people will have felt. Strangely, for the first part of mine The Undertaker wasn’t even there.

One of my favourite moments was when Shane appeared on Raw before Wrestlemania 32. Vince then announced Shane would compete at ‘Mania, in Hell In A Cell, against The Undertaker. The hairs on my neck stood up as we knew we’d see The Undertaker live for the first (and only) time.

This then moves forward to the event, and hearing the gong live. Even if the show was a dud, knowing what was coming that was a moment which will live with me for a long time, and I’m sure many will relate to whenever their first moment was when the lights went out and the gong sounded.

Leanne Culverhouse: Absolutely nothing can prepare you for hearing that gong in person. You know what it sounds like, you’ve experienced it hundreds of times but in person, it’s just something else.

April 22nd 2013, London’s O2 Arena. It was the first time I’d been to a TV taping and ‘Taker was on Raw for the first time in about three years. He made his entrance, The Shield surrounded the ring and out came Team Hell No for one of my favourite six-man tag matches ever. I was absolutely thrilled to see ‘Taker live.

James Dee: The moment when Undertaker raised Jeff Hardy’s hand after their ladder match on Smackdown. UT completely underestimated Jeff, but barely retained in one hell of a match many expected to be a squash.

Getting back on his bike, the champ rode back to the top of the ramp when Hardy, unable to stand on his own, dared to say, “You haven’t beaten me ‘Taker, I’m still standing”. Undertaker marched back down to the ring, pulled Hardy up by his hair and wound up a punch. At that moment, he looked into Jeff’s eyes and patted him on the back and raised his hand.

An absolutely flawless star-making turn that perfectly shows you don’t have to win matches to walk away the victor.