Opinion

#ThankYouTaker Top 5: The Undertaker’s Greatest Moments

With his retirement official, Mishal takes a look at his Top 5: The Undertaker’s Greatest WWE Moments.

Published

5 years ago

June 26, 2020

Mishal Shuhaiber

The Undertaker Top 5 Moments Chairshot Edit

With his retirement official, Mishal takes a look at his Top 5: The Undertaker’s Greatest WWE Moments.

We’re less than a week removed, but the announcement still lingers in the minds of anyone who’s been a wrestling fan for the last decade, or further than that.

In a year filled with controversy, tragedy & heartbreak, wrestling fans had to finally swallow the one day of their lives as fans that they’d for so long dreaded to experience, even contemplate for that matter, that being the inevitable retirement of the greatest character to ever enter a wrestling ring, The Undertaker himself, Mark Calloway. For many, myself included, The Undertaker was WWE to us, he had been a staple of the industry for so very long that picturing the wrestling scene without him would be borderline insulting to anyone considering how even when you were in doubt, the man would always come around when the time called for it. He was the last of a dying breed, one of the few left standing after The Attitude Era faded away & ushered in a new era of younger, fresher faces, somehow withstanding change with a gimmick that never seemed to age.

His farewell through the excellent 5-episode documentary series ‘The Undertakers Last Ride’ was reality smacking every wrestling fan in the face, that sooner or later every legend from the previous generation has his day & rides off into the sunset, much like anyone we hold dear to us. I personally appreciated the more personal, up-close look at the life of a man who for so long was just a character before anything else, this glance made everything feel so real, and understand that the time couldn’t have been better for an announcement like this.

Announcing his retirement in the manner that we got was unexpected, at least in the way I pictured him going out to some extent, but all of it felt oddly picture perfect. Despite the smaller scale, following a personal look into the lives of both The Undertaker & Mark Calloway, this all came across as what it was intended to be, ‘The Deadman’ going out just like he said, on his very own terms & nobody else’s. It all felt right, perfectly placed & pushing aside the aspiration fans had to see him go out in a more fashionable style, resulted in a goodbye that was humbling while leaving the door slightly opened should Vince McMahon ever come around to his door again.

I won’t get into the debate already occurring about if The Undertaker is ‘truly’ retired since, in this business, anything & everything is possible under the correct circumstances. What I will do, is take this very surreal time to talk about the moments that, to me, defined The Undertaker for the legend he has now cemented himself to be.

Consider this article a miniature tribute of sorts, one looking at the moments that engraved him in not just my mind, but so many millions who have followed him since 1990. Rather than go the standard root of listing endless matches, this article is all about the moments & which ones engraved The Undertaker into the history books for generations to come.

5. 1-0 – WrestleMania VII

Undertaker’s victory over Jimmy Snuka at WrestleMania VII is less about the overall quality of the match, which was nothing to write home about, and more about the significance of this victory in the wider context of things all these years later. At the time Undertaker was a one of a kind figure in an industry already on the brink of change, bringing his unique aura & persona to the ring like nobody around him could, which gave every match or segment involving him a feeling unlike any other.

WrestleMania VII was the beginning of what to this day, is amongst the most iconic winning streaks across any sport, period. Undertaker’s win over Jimmy Snuka was decisive, emphatic & made a mark that would end up running two decades, amounting a list comprising of some of the most iconic in the entire industry. Triple H, Shawn Michaels, Ric Flair, Edge, Batista, CM Punk, Randy Orton, Kane, Diesel, Sycho Sid & a dozen others all threw caution to the wind & took their chance to try and defeated ‘The Deadman’ on the largest stage the industry had to offer, but one by one they fell victim to the WWE’s most respected talent to grace a ring in any capacity.

Eventually, as history showed, The Undertaker much like every other WWE superstar, was mortal, with his streak coming to a shocking conclusion at WrestleMania XXX in a moment that, in my opinion, stands as the most shocking in company history. While the decision to end Undertaker’s streak does have its critics, the thing it displayed more than anything was that over time it wasn’t about an undefeated streak, but about preserving a character that has withstood the test of time in a business that so frequently rejects those from previous generations. The streak may have come to an end in 2014, but The Undertaker as a character lived on far beyond that, and for many was the defining trait to lead him to where he stands in the eyes of fans today.

4. The Deadman Rises, Again – WrestleMania XX

I feel like this particular choice is more of a personal one considering how little attention this match or the events leading up to it are discussed nowadays. But witnessing The Undertaker return in full form at WrestleMania XX was simply surreal.

In the months leading up to this match, we had witnessed his burial at the hands of his brother Kane, setting the stage for a colossal return & a rematch between the two ‘Brothers of Destruction’ on the very grounds they did battle almost a decade prior. Similar to his match with Bray Wyatt, The Undertaker remained absent for virtually all of the build to this match, instead of taunting his ‘brother’ face-to-face, opted to intimidate him with his vintage mind games, vignettes teasing the 2nd coming of the original Deadman himself & a teaser appearance at the 2004 Royal Rumble that remains incredible to this day, thus leaving much of the build on Kane himself to carry forward.

The result of all this build amounted to the long-awaited return of the original Undertaker, and not his ‘American Badass’ counterpart we’d been watching for the last five years. Built-up by an incredibly nostalgic entrance, the return of Paul Bearer at his side & a refreshed character thrust into an entirely new generation, what we got was exactly what it needed to be. The match was nowhere near the quality of their WrestleMania match years prior to this but was never meant to be, The Undertaker, The Deadman, The Demon of Death Valley, he was back and better than ever.

While I wouldn’t consider it one of the best of his career by any stretch from an in-ring perspective, it was a pivotal moment that took The Undertaker back to his roots, but also showed that his gimmick is one of the select few that will always have a place in any era of the business.

3. The American Badass arrives – Judgement Day 2001

The most important aspect of any iconic figure in entertainment is to always flow & change with the times to some degree. Changing up your character or story is the best way to adapt to new environments, something professional wrestling is always becoming accustomed to considering how rapid the fanbase changes over such short spaces of time.

When The Undertaker showed up at Judgement Day 2001, his gimmick was something I remember being fairly divided on despite being a lot younger than I am now. Losing the core of his previous take on the character was a big knock to me, stripping away a certain aura that made him unique, little did we know this character came along with his own brand of uniqueness. ‘The American Badass’ felt like a more grounded Undertaker, probably one you could sit down to have a drink with before he beats you into a pulp.

His interference during the main event between The Rock & Triple H sent the live crowd that evening into a complete frenzy, not just because of his return after months out of action but the absolute awe of what he returned as, nothing like what the fans were used to seeing in the slightest. Sporting a motorcycle, bandana, sunglasses but retaining the dark coat & mystique we knew him for, Undertaker seemingly reinvented himself in a matter of seconds with the acceptance of everyone. This gimmick wouldn’t be short-lived either, resulting in multiple title wins & some of the most physically enduring matches of the man’s career as a whole. It seems like the wrestling community is always a bit divided on what we got this day back in 2001, but it’s a moment I’ll remember for as long as I can.

2. Going out on top – WrestleMania 36

My personal stance on this match has obviously shifted following the actual ‘Last Ride’ series & what it means within the context of the show, but I can’t think of a better way for a wrestler, especially one on the calibre of The Undertaker, to go out to. Considering the circumstances that not just this match but the entire company were under at that point in time with COVID-19 turning the entire planet upside down, it’s a miracle that this ended up being as good as it did once it debuted on the night of WrestleMania this past year.

Besides being an incredibly entertaining brawl on its own, the match stands as one of the most creative in company history. Its presentation alone is surreal when you really look into what the match was pitched as, being forceable changed from your standard wrestling match both Undertaker & AJ Styles clashed within the confines of something no fan imagined in their head. In terms of character work, it’s amongst the best of Undertaker’s entire career. Combining every version of his legendary character into one confined package, from ‘The American Badass’, ‘The Deadman’ & most importantly, Mark Calloway himself. In a way, the match felt like a tribute to everything the character has represented for close to three decades and delivered in style.

As far as closing out a career goes in the wrestling industry, you couldn’t ask for a better sendoff. Having it done in front of a live audience of tens of thousands of fans would have been preferable to most of us, considering the legacy he holds in our minds, but doing it against one of the very best wrestlers alive today in AJ Styles is arguably the highest note possible to achieve at this stage in a career that’s accomplished virtually everything there is to accomplish.

Not only is this going to set a new bar for how WWE presents future matches across the board but sent Undertaker out doing what he strives to do, pressing the business forward.

1. The ‘End of an Era’ – WrestleMania XXVIII

No moment in the history of professional wrestling, at least within this modern era, will ever replicate how much this one meant to so many different clusters of wrestling fans.

To me, wrestling is all about moments like these. Ones that will stand forever, that feel earned & signify something bigger than just another match on a card, but something we’ll pass onto whoever follows the business next.

WrestleMania XXVIII was a special night, for everyone. It was an evening packed with dream matches signifying different things to different fans, the main event that stands as the biggest buyrate the sport has seen to date & a match that quite literally marked the ‘End of an era’ (until WWE ruined that moment roughly six years later, but let’s not speak of that). Placing this match inside Hell In A Cell was the icing on the cake, pitting not just two of the most iconic stars the industry has ever seen against one another, but in a match that both made famous over the course of their legendary careers.

Undertaker vs Triple H was one of the very few WrestleMania matches I would consider ‘elite’, a category for the very best in all aspects of what it’s trying to sell to audiences. From the action, storytelling, high spots, frantic live audience or Jim Ross providing some of the best lines of his career, everything about this is what wrestling personifies. What made this event even more special, was what occurred following that unprecedented 21-0 record solidifying itself, seeing Undertaker, Triple H & Shawn Michaels stand side-by-side in front of a crowd of almost 80,000 fans take one final bow before going behind the curtain, thus closing one of the most important chapters in the history of professional wrestling.

When it comes down to the moments we’ll remember The Undertaker most fondly for, it’s hard not to chuck this to the top of the list. It was his 4th straight WrestleMania performance worthy of a 5-star rating, capturing him at the peak of his career & having him stand next to two men that helped him craft his best work in the ring without question. I understand this topic is up for debate, but it’s hard to get any better than this.

About Chairshot Radio Network

Launched in 2017, the Chairshot Radio Network presents you with the best in sports, entertainment, and sports entertainment. Wrestling and wrestling crossover podcasts + the most interesting content + the most engaging hosts = the most entertaining podcasts you’ll find!

MONDAY - Bandwagon Nerds (entertainment & popular culture)

TUESDAY - Musical Chairs (music) / Hockey Talk (NHL)

WEDNESDAY - The Greg DeMarco Show (wrestling)

THURSDAY - Keeping the news ridiculous... The Oddity / Chairshot NFL (NFL)

FRIDAY - DWI Podcast (Drunk Wrestling Intellect)

SATURDAY - The Mindless Wrestling Podcast

SUNDAY - The Front and Center Sports Podcast

CHAIRSHOT RADIO NETWORK PODCAST SPECIALS

Attitude Of Aggression Podcast & The Big Five Project (chronologically exploring WWE's PPV/PLE history)

TheChairshot.com PRESENTS...IMMEDIATE POST WWE PLE REACTIONS w/ DJ(Mindless), Tunney(DWI) & Friends

Patrick O'Dowd's 5X5

Classic POD is WAR

Chairshot Radio Network Your home for the hardest hitting podcasts... Sports, Entertainment and Sports Entertainment!

All Shows On Demand

Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!

Up Next

#SpeakingOut: Where Do We Go From Here?

Don't Miss

Cook: Two Strikes, CHIKARA’s Out

Opinion

Chairshot Staff Picks: WrestleMania 41 Las Vegas

Time for The Chairshot personalities to put their money where their mouths are! WreslteMania 41 predictions from the “expert” staff at TheChairshot.com and Chairshot Radio Network.

Published

20 hours ago

April 18, 2025

PC Tunney

Ladies and gentlemen, welcome back to the Chairshot Staff Picks. And what better setting than WrestleMania for this article to return! This 41st edition has one of the most stacked rosters in WWE history. So, without further ado, let us get to the predictions and prognostications…

AJ – The New Day
Andrew – The New Day – No one seems to hold tag titles long anymore.
Dave – The New Day – They have earned it.
DJ – The New Day – Feel tha Powah!
DPP – War Raiders – Big E distraction.
Jason – The New Day – We are not getting E in a working capacity though everyone wants it.
Patrick – The New Day – WWE doesn’t care about this match, so why should I?
Rey – The New Day – Its a New Day, bruh.
Rob – The New Day – New Day rocks and wins!
Greg – The New Day – New. Day wins. New. Day wins!

Tunney’s Take: War Machine – Yes, WAR MACHINE. I have personally had the pleasure of throwing back a few cold ones with these guys on more than one occasion. Not only being tag champs in WWE but defending the titles at Mania and against The New Day is really cool for me as a long-time fan. Would it be fun to see The New Day have another title run.. YES. I think it’s smarter to give the War Raiders a big Mania W.

Chairshot Pick: THE NEW DAY 9-2

AJ – Jade Cargill
Andrew – Jade Cargill – She needs to stay a dominant force.
Dave – Jade Cargill – Gotta gear her up for the long term.
DJ – No contest – Naomi puts another beat down on Jade.
DPP – Jade Cargill – Nervous for how this match will go.
Jason – Naomi – Way more runway with Naomi as a bad guy. Keep it going!
Patrick – Jade Cargill – Jade gets her revenge.
Rey – Jade Cargill – Best non-title feud going. Naomi should win but Jade sneaks by.
Rob – Naomi – Naomi gets help to win.
Greg – Jade Cargill – They ain’t beating Jade here.

Tunney’s Take: Jade Cargill – I imagine WWE sees Jade’s ceiling much higher than Naomi’s. What better way to keep Jade climbing the ladder towards a World Title than to pick up a decisive victory in Vegas!

Chairshot Pick: Jade Cargill 8-2-1

AJ – Jacob Fatu – “AJ does a pretty good LA Knight impersonation” – PC Tunney
Andrew – Jacob Fatu – I’m biased, Jacob for President.
Dave – Jacob Fatu – Getting gold back in the Bloodline is smart.
DJ – Jacob Fatu
DPP – Jacob Fatu
Jason – Jacob Fatu – Thanks for coming pal, YEAH!
Patrick – Jacob Fatu
Rey – Jacob Fatu – C’mon cuz! All gas no brakes with it. Yadadamean??
Rob – LA Knight – Solo costs Jacob.
Greg – LA Knight – Solo screws Jacob.

Tunney’s Take: Jacob Fatu – It has been quite the journey for the Samoan Werewolf. I feel like that journey and the positive turn around it has taken deserves to be rewarded. Let’s see what Jacob can do on his own. Plus, LA Knight is ready to challenge for a World Title.

Chairshot Pick: Jacob Fatu 9-2

AJ – Tiffany Straton
Andrew – Tiffany Straton – I hate Charlotte Flair, no objectivity here.
Dave – Charlotte Flair – Tiffy might be the future, but she kinda failed the litmus test.
DJ – Charlotte Flair – The Queen crowns the freshman.
DPP – Tiffany Stratton
Jason – Charlotte Flair – Tiff wasn’t ready for this spot. Charnos is inevitable.
Patrick – Charlotte Flair – Lol Charlotte wins.
Rey – Charlotte Flair – Tiffany SHOULD win but, if Charlotte can squash, she will.
Rob – Charlotte Flair – Charlotte gets number 15.
Greg – Tiffany Stratton – Lol Charlotte wins. (Actually she doesn’t)

Tunney’s Take: Charlotte Flair – Charlotte needs the title for the first time in her career. Tiffy has had a nice run but now needs to take that all important step of not losing momentum after losing the title. Despite the drama and lackluster build here, I see a really good match coming this weekend from these two.

Chairshot Pick: Charlotte Flair 7-4

AJ – El Grande Americano
Andrew – El Grande Americano – I’d like to see Gable gain some momentum. Rey is Teflon.
Dave – El Grand Americano – He needs a marque win much more than Rey.
DJ – Rey Mysterio
DPP – El Grande Americano – Grande wins with the switcheroo to prove he is not Gable.
Jason – Rey Mysterio – Unmask Grande at the end. It is fun but has a shelf life.
Patrick – El Grande Americano – TOTALLY NOT CHAD GABLE
Rey – Rey Mysterio – Someone’s mask is coming off and it ain’t Rey.
Rob – El Grande Americano
Greg – Rey Mysterio – Hall of Famer wins but doesn’t take the mask.

Tunney’s Take: Rey Mysterio – Go listen to DWI 471. DP, Greg and I lay out exactly what this match should be, FUN! Multiple Americanos!!!

Chairshot Pick: El Grande Americano 6-5

AJ – Jey Uso
Andrew – Jey Uso – Kinda booked themselves into a corner here.
Dave – Jey Uso – It just makes sense.
DJ – Jey Uso – Jey YEETS all over The Ring Genreal.
DPP – Jey Uso – Jey wins after normal Gunther beating.
Jason – Jey Uso – Land the plane man. YEET
Patrick – Jey Uso – Jey has earned this one.
Rey – Jey Uso – YEEEEEEEEEEEET!
Rob – Jey Uso – YEET
Greg – Jey Uso – If Jey loses we riot. We don’t cause he wins.

Tunney’s Take: Jey Uso – ‘Til sweat drop down my balls, ‘Til all these bitches crawl, ‘Til all… YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET YEET!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Chairshot Pick: Jey Uso 11-0

AJ – Roman Reigns
Andrew – Seth Rollins – I can see Rollins being the last piece of Team Rock.
Dave – Roman Reigns – I can’t see Roman losing two years in a row.
DJ – Seth Rollins – Paul Heyman is a Seth Freakin Rollins guy.
DPP – Seth Rollins – The Rock helps Rollins.
Jason – Roman Reigns – Seth’s favor is a red herring. Make-A-Wish Brooks got his main, now look at the lights.
Patrick – Seth Rollins – Seth Rollins… Paul Heyman guy.
Rey – Seth Rollins – I smeeeeellllllll a new soul to sell.
Rob – Roman Reigns – Paul Heyman helps Roman win.
Greg – Seth Rollins – Brock Lesnar returns to help Seth win.

Tunney’s Take: CM Punk – I really have no idea here. I picked Punk because nobody else did. This is going to be professional wrestling cinema at its finest. The story is thick and neatly woven. All the participants are legends and so are the potential party crashers. Will The Rock stick his nose in here? Will Brock Lesnar return to play a factor? Obviously, Paul Heyman has a Plan A… but what is it? All these questions and more will be answered Saturday as night 1 will definitely go out with a bang!

Chairshot Pick: Seth Rollins 6-4-1

AJ – Iyo Sky
Andrew – Iyo Sky – Rhea vs Bianca doesn’t need a belt to be compelling.
Dave – Rhea Ripley – Going with Rhea barely, hoping Iyo wins.
DJ – Iyo Sky – Unfinished business.
DPP – Iyo Sky – Rhea and Bianca are too consumed with each other.
Jason – Iyo Sky – More layers to Rhea/Bianca. Iyo rules.
Patrick – Iyo Sky – Iyo stole the build and gets the win.
Rey – Iyo Sky – Smart money is on the underdog champ.
Rob – Iyo Sky – Iyo survives.
Greg – Bianca Belair – Naomi helps Bianca win and turn heel.

Tunney’s Take: Rhea Ripley – Rhea is the best women’s wrestler in the world. Give her the biggest win on the grandest stage of them all!!! Bianca needs to go full heel. Iyo has been amazing in this build.

Chairshot Pick: Iyo Sky 8-2-1

AJ – Dominik Mysterio
Andrew – Finn Balor – I can see a Judgement Day meltdown incoming.
Dave – Bron Breakker – Bron is about to become a MegaStar.
DJ – Bron Breakker – Judgement Day implodes.
DPP – Dominik Mysterio – Finn take the pin.
Jason – Penta – I literally do not care because the winner is us, the fans.
Patrick – Bron Breakker – The WWE doesn’t care about this matchup, so why should I?
Rey – Dominik Mysterio – Only match without a clear winner. I choose chaos.
Rob – Bron Breakker – Finn and Dom cancel each other out.
Greg – Dominik Mysterio – Dom steals the pin from Bron, on Finn.

Tunney’s Take: Bron Breakker – The case can be made for any of these four to walk away with the most prestigious non-World title in pro wrestling history. The short of it is though that the Main Event picture isn’t really readily accessible for Breakker right now. Let this IC reign go through the summer, to SummerSlam.

Chairshot Pick: Bron Breakker 5-4-1-1

AJ – Damian Priest – “AJ does a pretty good Drew impersonation” – PC Tunney
Andrew – Drew McIntyre – Priest has not been interesting in this face incarnation.
Dave – Drew McIntyre – Time for Drew to get that win back.
DJ – Fuck finish – To be continued at Backlash.
DPP – Drew McIntyre – Physical matchup!
Jason – Drew McIntyre – Either one is fine here.
Patrick – Drew McIntyre – With two eyes, Drew turns the tide.
Rey – Drew McIntyre – Low key match of the weekend.
Rob – Damien Priest
Greg – Damien Priest – Priest wins, Drew tweets about it half hour later.

Tunney’s Take: Drew McIntyre – With the addition of the Street fight rules, these two behemoths have a really good chance to have one of the best matches of the entire weekend (winks at Rey Ca$h-A-Mania)! I do wonder what is next for both of these talents moving forward. Priest has staled since leaving the Judgement Day and Drew seems stuck in the same cycle for a while now. Very interested to see what the summer holds for this pair.

Chairshot Pick: Drew McIntyre 7-3-1

WHO WILL BE RANDY’S OPPONENT?!?

AJ – Nick Aldis – Orton wins
Andrew – Orton and Aldis vs Solo and Tama – Orton and Aldis win
Dave – Someone is getting an RKO!
DJ – A segment w/ the Wyatt s6cks.
DPP – Rusev – Aldis introduces Rusev who defeats Orton.
Jason – Nick Aldis – You got one more in ya, bubba. Aldis wins!
Patrick – Nick Aldis
Rey – Solo then Rusev – Solo in a squash and Rusev MATCHKA(wins)
Rob – Nick Aldis – Aldis proves himself, Orton wins.
Greg – Nick Aldis – Orton beats Aldis, they shake after.

Tunney’s Take: I would really love to see a singles match between Orton and Aldis. More likely this is some type of involvement with Solo and Tama. Rusev as a surprise challenger would be cool but, I feel that would be better left for RAW. An impromptu Goldberg retirement match would be crazy and fun, yet highly unlikely and illogical. Whatever happens, best believe exactly what Dave Ungar said, “Someone is getting an RKO!”.

AJ – Logan Paul
Andrew – AJ Styles – Logan doesn’t need the rub and should stay upper mid card.
Dave – Logan Paul – It’s the smart move and would be a statement win for Paul.
DJ – Logan Paul – Kross gets involved somewhere.
DPP – AJ Styles – AJ wins a great high-flying match.
Jason – AJ Styles – Just enjoy it or get a beer, nerds.
Patrick – Logan Paul – Logan Paul will main-event Mania sooner than later…
Rey – Logan Paul – Pass the torch, my wily vet.
Rob – Logan Paul – Kross helps Paul win.
Greg – AJ Styles – Styles wins after Paul’s cheating backfires.

Tunney’s Take: Logan Paul – Logan seems to really have dedicated himself to becoming great in this business. Anyone with that type of goal must have a World title on their mind. Beating AJ at Mania will be a great springboard for Logan into the Main Event sooner than later (winks at Patrick O’Dowd).

Chairshot Pick: Logan Paul 7-4

AJ – Liv & Raquel
Andrew – Liv & Raquel – Not really a fan of Lyra, she needs more work.
Dave – Liv & Raquel – This Bayley and Lyra team makes no damn sense.
DJ – Liv & Raquel – Bayley crashes out.
DPP – Liv & Raquel – Bayley continues a potential heel turn tease.
Jason – Bayley & Lyra – Finish the story!
Patrick – Bayley & Lyra – The WWE doesn’t care about this matchup, so why should I?
Rey – Liv and Raquel – Bayley want a title but it ain’t the ones in this match.
Rob – Liv & Raquel – Champs retain.
Greg – Liv & Raquel – Liv and Raquel retain thanks to Carlito and maybe JD.

Tunney’s Take: Liv & Raquel – Liv and Raquel need to be kept as the cornerstone of the women’s tag division for a lengthier period of time. Building tag teams in this division is difficult enough, let alone without a North Star.

Chairshot Pick: Liv & Raquel 9-2

AJ – Cody Rhodes
Andrew – Cody Rhodes – They are mentioning it so much, I don’t think 17 happens.
Dave – Joh Cena – Record falls and we head to summer with a built-in storyline.
DJ – John Cena – Some kind of Final Boss involvement.
DPP – John Cena – Cena wins and retires on RAW.
Jason – John Cena – Story’s over, “Captain” BIG MATCH JOHN.
Patrick – John Cena – A record breaking night for Cena.
Rey – John Cena – They’d be really stupid to turn John just to lose. (Post-Mania: Rock, Cena, T Scott, Seth & Drew, TEAM Corporate)
Rob – Cody Rhodes – Cody surprises us with the W.
Greg – Cody Rhodes – Cody wins to piss off Rock and set the table for Cena to turn back face. Crowd is behind Cena all the way through.

Tunney’s Take: Cody Rhodes – They had me until the threat of retirement. Been there. Done that. Didn’t fall in love with it back then. I love John Cena. I love this final run. John will get his 17th just not here. I expect nothing less than an absolute GEM of a match here to close WrestleMania 41. This has all been, is, and will continue to be about Cody Rhodes. WM40 defeats Roman Reigns. WM41 defeats John Cena. WM42 defeats The Rock (The Final Boss).

Chairshot Pick: John Cena 6-5

In closing I want to thank everyone on the panel for participating with their picks! You can follow each prognosticator/podcaster on X @ the handles below. We wait all year for this so remember three things… be respectful of others, comparison is the thief of joy and HAVE FUN!

AJ – @PhenomenalAJB
Andrew – @IWCWarChief
Dave – @AttitudeAgg
DJ – @TheMindlessPod
DPP – @itsmeDPP
Jason – @JediFett
Patrick – @WrestlngRealist
Rey – @itsreycash
Rob – @rbonne1
Greg – @gregdemarco44
PC – @PCTunney
TheChairshot.com – @ChairshotMedia

For the latest, greatest and up to datest in coverage, opinions, and podcasts ALWAYS #UseYourHead and visit TheCharishot.com

Prowrestlingtees.com/TheChairshot plenty of GREAT t-shirt designs! Makes an awesome gift!!

About Chairshot Radio Network

MONDAY – Bandwagon Nerds (entertainment & popular culture)

TUESDAY – Musical Chairs (music) / Hockey Talk (NHL)

WEDNESDAY – The Greg DeMarco Show (wrestling)

THURSDAY – POD is WAR

FRIDAY – DWI Podcast (Drunk Wrestling Intellect)

SATURDAY – The Mindless Wrestling Podcast

SUNDAY – The Front and Center Sports Podcast / The Oddity… Keeping the news ridiculous!

CHAIRSHOT RADIO NETWORK PODCAST SPECIALS

Attitude Of Aggression Podcast & The Big Five Project (chronologically exploring WWE’s PPV/PLE history)

TheChairshot.com PRESENTS…IMMEDIATE POST WWE PLE REACTIONS w/ DJ(Mindless), Tunney(DWI) & Friends

Patrick O’Dowd’s 5X5

Chairshot Radio Network
Your home for the hardest hitting podcasts… Sports, Entertainment and Sports Entertainment!

All Shows On Demand

Listen on your favorite platform!

About Chairshot Radio Network

MONDAY - Bandwagon Nerds (entertainment & popular culture)

TUESDAY - Musical Chairs (music) / Hockey Talk (NHL)

WEDNESDAY - The Greg DeMarco Show (wrestling)

THURSDAY - Keeping the news ridiculous... The Oddity / Chairshot NFL (NFL)

FRIDAY - DWI Podcast (Drunk Wrestling Intellect)

SATURDAY - The Mindless Wrestling Podcast

SUNDAY - The Front and Center Sports Podcast

CHAIRSHOT RADIO NETWORK PODCAST SPECIALS

Attitude Of Aggression Podcast & The Big Five Project (chronologically exploring WWE's PPV/PLE history)

TheChairshot.com PRESENTS...IMMEDIATE POST WWE PLE REACTIONS w/ DJ(Mindless), Tunney(DWI) & Friends

Patrick O'Dowd's 5X5

Classic POD is WAR

Chairshot Radio Network Your home for the hardest hitting podcasts... Sports, Entertainment and Sports Entertainment!

All Shows On Demand

Let us know what you think on social media @ChairshotMedia and always remember to use the hashtag #UseYourHead!

Blog

DeMarco: Top 5 Non-Title WrestleMania Matches In WWE History

Not all WrestleMania classics had titles on the line. Dive into the top 5 non-title matches that stole the show & defined legacies. #WrestleMania #WWEHistory

Published

3 days ago

April 16, 2025

Greg DeMarco

Shawn Michaels Kurt Angle WrestleMania 21

Not all WrestleMania classics had titles on the line. Dive into the top 5 non-title matches that stole the show and defined legacies.

WrestleMania is the Showcase Of The Immortals, but it’s not always the championship matches that steal the show—or define careers. In fact, some of the most iconic, business-defining, and emotionally resonant contests at the Grandest Stage of Them All didn’t feature a title at all. These matches succeeded because of character work, in-ring execution, and the kind of storytelling that sells tickets and moves merch.

Here are the five best non-title matches in WrestleMania history—at least, according to me!

5. The Rock vs. Hulk Hogan – WrestleMania X8 (2002)

This was never going to be a five-star technical clinic—but it was always going to be the moment. “Icon vs. Icon” was a tagline, sure, but it was also the reality: the biggest star of the ‘80s vs. the biggest star of the Attitude Era. And Toronto turned it into magic. Hogan walked in a heel but walked out immortal (again), with the SkyDome shaking on every punch, every look, every gesture.

What made this work was its self-awareness. Rock and Hogan read the crowd and flipped roles mid-match—Rock became the arrogant aggressor while Hogan Hulked Up to thunderous applause. It’s not often a non-title match headlines a card emotionally the way this one did, but it dominated every headline and highlight reel.

4. Owen Hart vs. Bret Hart – WrestleMania X (1994)

Sibling rivalries don’t usually lead to technical masterpieces, but then again, this wasn’t your average family drama. Owen and Bret opened WrestleMania X with a wrestling clinic that stood tall over a night packed with title changes. Owen needed to prove he was more than Bret’s little brother, and he did it by out-wrestling the best wrestler in the company. Clean. One-two-three.

It wasn’t just a great match—it was perfect storytelling. Owen’s victory, contrasted with Bret’s later world title win, set the tone for an entire year of brother-vs-brother tension. Bret became champion, but Owen had the moral victory—and all the bragging rights. This is proof that opening matches can steal the show.

3. The Undertaker vs. Shawn Michaels – WrestleMania 25 (2009)

If WrestleMania moments could be trademarked, this match would be the reason why. The Undertaker vs. Shawn Michaels wasn’t about championships—it was about legacy. Michaels wanted to be the man who ended The Streak. The build was steeped in biblical imagery: light vs. dark, heaven vs. hell. And the match? Pure perfection. Each man brought everything they had—near-falls, psychology, reversals that had 70,000+ people gasping in unison.

It was 30 minutes of generational storytelling that transcended pro wrestling. And here’s the kicker—it wasn’t even the main event. Yet it dwarfed everything that followed. Meltzer gave it 4.75 stars, fans gave it their hearts, and WWE gave it a sequel the next year. A match so good it forced the company to run it back—because lightning actually struck.

Now, if THIS MATCH is #3, what could possible be #2 and #1…

2. Bret Hart vs. “Stone Cold” Steve Austin – WrestleMania 13 (1997)

This wasn’t just a match—it was the turning point of an era. The Submission Match between Bret Hart and Steve Austin was as violent as it was poetic, with Ken Shamrock enforcing the rules and the Chicago crowd growing more frenzied by the second. The brilliance? The shift. Bret Hart, the traditionalist hero, grew darker and more self-righteous by the second, while the disrespectful anti-hero Austin refused to quit, even when drowning in his own blood. There was no title on the line, but the stakes felt bigger than gold.

The infamous double turn changed the business. Austin’s defiance turned him into the voice of a new generation of fans—blue collar, anti-authority, Attitude Era. Meanwhile, Bret would go on to lead the heel Hart Foundation. WWE didn’t need a championship to create a moment that catapulted Austin into superstardom and ignited the company’s hottest era. This match is business-first booking at its absolute best.

1. Kurt Angle vs. Shawn Michaels – WrestleMania 21 (2005)

Dream matches often disappoint. This one didn’t. At WrestleMania 21, Olympic gold medalist Kurt Angle went hold-for-hold and spot-for-spot with Mr. WrestleMania himself, and together they delivered a masterclass in in-ring psychology. Every sequence had stakes, every near-fall had meaning. It was a stylistic war: Michaels’ heart vs. Angle’s intensity.

Angle forcing Michaels to tap was a statement—it told fans that pure wrestling, not just spectacle, could still main-event caliber storytelling without any need for a title. Michaels sold the ankle lock like death, and Angle’s post-match collapse sold the moment as a hard-fought war. This is the kind of match that keeps purists up at night, smiling, and leaves the storytelling fans like myself as happy as can be!

10 Honorable Mentions (Not Honorable, Just For The Heck Of It)

Edge vs. Mick Foley – WrestleMania 22 (2006)
A hardcore war that solidified Edge as a top-tier main eventer. That flaming table spear is still played in every Edge highlight reel.
AJ Styles vs. Shane McMahon – WrestleMania 33 (2017)
Everyone expected smoke and mirrors—what they got was a surprisingly technical, high-energy opener that kicked off the show right.
The Undertaker vs. Triple H – WrestleMania 28 (2012)
“End of an Era” wasn’t just a tagline. The Hell in a Cell match, with HBK as referee, was a brutal epilogue to a generation’s legacy.
Shawn Michaels vs. Chris Jericho – WrestleMania XIX (2003)
A student-teacher battle of wills. Jericho’s low blow post-match was the perfect heel punctuation to a career-defining contest.
Randy Orton vs. Seth Rollins – WrestleMania 31 (2015)
The greatest RKO of all time. That curb stomp reversal belongs in a museum.
Floyd Mayweather vs. Big Show – WrestleMania XXIV (2008)
More sports-entertainment than wrestling, but a crossover moment that made mainstream headlines and paid off with a great finish.
Roddy Piper vs. Adrian Adonis – WrestleMania III (1987)
A retirement match with big heat, a hot crowd, and Piper walking off into the sunset (for a minute).
The Firefly Funhouse Match – John Cena vs. Bray Wyatt – WrestleMania 36 (2020)
Cinematic weirdness at its best. A meta masterstroke that broke Cena down in layers.
Bad Bunny & Damian Priest vs. The Miz & John Morrison – WrestleMania 37 (2021)
Bad Bunny stunned everyone. He didn’t just belong—he elevated the show.
Rey Mysterio vs. Dominik Mysterio – WrestleMania 39 (2023)
Father vs. son in a grudge match that played perfectly off real-life drama and Hall of Fame weekend emotions.

Some of these matches shaped legacies. Others shifted eras. But all of them proved that the most memorable moments at WrestleMania don’t need a title—they just need truth in the storytelling and fire in the execution.