The Magnificent Seven: The Top 7 Moments from the WrestleManias 21-30

As we close in on WrestleMania, I decided to dedicate my last three columns leading up to the show to recalling the greatest WrestleMania moments. Columns taking on the entire WrestleMania catalog in that vein are a bit unwieldy given how many shows there are to consider and given that, particularly in recent years, shows are so long. In the interest of breaking things down and recognizing a handful of underappreciated moments, I’m going decade by decade. Two articles ago, I looked at the seven best moments from WrestleManias 1 through 10, last time I focused on WrestleManias 11 through 20, and for this final Magnificent Seven before WrestleMania will look at WrestleManias 21-30. Yes, that leaves out 31-33—we’ll get back to those someday, maybe when they have more historical context to consider.

This column is concerned with memorability of the moment itself, its impact on WWE history, and how it played off the history to precede it. As always, my personal opinion weighs heavily, though I did make an effort to distinguish opinion from objective greatness here.

#7. Edge Wins the First Money in the Bank Briefcase at WrestleMania 21

It’s hard to imagine a WWE landscape nowadays without Money in the Bank. It wasn’t until two decades of WrestleMania had gone by, however, that the briefcase was first suspended over the ring. Six men would pursue it in a brilliantly chaotic ladder match.

Few Money in the Bank matches can really compete with the original (though the most recent iteration that main evented last summer’s Money in the Bank PPV just might have surpassed it in my book). Without an established formula for how the briefcase might be used, there was little reason to assume that a heel was the most logical choice to win, and without a track record for success, there was no guarantee that whoever won was actually heading for the main event for more than a single match.

Money in the Bank would end up being exactly the right vehicle to get Edge over as a legit main event star, and while he was arguably on his way to that destiny before WrestleMania 21, winning a ladder match was a perfectly poetic way to take his singles career to the next level. Better yet, the final moments the match, which featured Edge both sneakily and viciously attacking Chris Benoit’s arm to beat him off the ladder represented some of the hallmarks of Edge’s career. This was the finish to an excellent match, and in a WrestleMania that saw John Cena and Batista each win their first world titles, and Randy Orton give The Undertaker’s streak a meaningful challenge, Edge was the unlikely fourth new breed main eventer to reach new heights coming out of the show.

As a historical footnote, it’s also worth mentioning that the unofficial ten-year anniversary of the first Money in the Bank Ladder Match, WrestleMania 31, saw the first Money in the Bank cash-in at a WrestleMania as Seth Rollins did the Edge tradition proud in sneaking his way into a main event scenario and walking out the unlikely champion.

#6. The Undertaker Kicks Out of The Superkick-Pedigree Combo at WrestleMania 28

I’m sure this choice will get some dissent, but it still stands out to me as one of the moments I remember best from watching a WrestleMania in this era live.

By WrestleMania 28, at which The Undertaker squared off with Triple H in a Hell in a Cell match, I didn’t expect that The Undertaker’s undefeated streak at WrestleMania would ever end. And yet here we were, watching The Dead Man square off with Triple H. Triple H who’d stolen wins I never would have predicted at WrestleManias 16 and 19. And he had his real life and kayfabe best friend Shawn Michaels as the guest referee.

If the streak were to end, wouldn’t it have to involve shenanigans?

And if Shawn Michaels were to nail The Dead Man with one of the most over finishers in wrestling—Sweet Chin Music—only for him to turn directly into Triple H’s unbeatable Pedigree, would it be possible for even The Undertaker to kick out of that?

The bottom line is, in an era when the streak was bulletproof, the super kick-into-a-Pedigree false finish actually had me biting. When The Phenom kicked out, it was a legit mark out moment. I was never a fan of the preceding Undertaker-Triple H matches at WrestleMania, but this moment, surrounded by a stellar match, succeeded in winning me over, putting aside my critical instincts to enjoy the show.

#5. The Undertaker Pins Shawn Michaels at WrestleMania 25

WrestleMania 25 was not a great ‘Mania. Mind you, it wasn’t one of the worst, but it featured a middling card by WrestleMania standards, and the matches hadn’t really exceeded any expectations or offered meaningful surprises—that is, until The Undertaker vs. Shawn Michaels.

Full disclosure, I was in Houston to watch this match live, and I don’t suspect I ever have, or necessarily ever will see a better one in-person. This was a positively epic showdown between two legit legends. While each may have been past his physical prime, both were masters of ring psychology and assembled an absolutely breathtaking work of art in the ring for this bout.

In a sense, I’d like to find a place for this match—the best of the decade I’m evaluating—higher in the countdown. It lacked a a pure great moment to push it into the top four in my book, but the clean pin following a Tombstone, to cap this half hour instant classic is solid enough to snag the number five spot.

#4. Edge Spears Mick Foley Through a Flaming Table at WrestleMania 22

In my previous countdown, I ranked Edge leaping from a ladder to spear Jeff Hardy at WrestleMania 17 as the second best moment from WrestleManias 11-20. I ranked the moment this highly based on a combination of an electric high spot and the metaphorical leap that Edge and Hardy were taking toward more permanent relevance and eventual main event status.

The journey continued with this, Edge’s most iconic spear to fall between WrestleMania 21 and WrestleMania 30. After cashing in the first Money in the Bank contract, and a brief reign as WWE Champion, Edge took a step back just in time for WrestleMania, out of the main event picture and back to the upper mid-card. His dance partner wasn’t just any star of comparable status, however, but rather a legend approaching the end of his ability to put on a great match—Mick Foley.

Whether Foley was drawing blood from Edge by wrapping his own body in barbed wire, or delivering a barbed-wire-assisted Mandible Claw on both Edge and Lita, or throwing Edge into thumbtacks this match pushed the limits of how hardcore WWE would go at the time and, in the process, cemented Edge as a top star for his willingness to absorb punishment, and proving he could dish it out as well as he could take it.

This dynamic culminated in the match’s final spot. The table had been set up at ringside and doused in lighter fluid earlier. At the climax, Lita set the thing blaze, and Edge proved his willingness to dive into the fire both metaphorically and quite literally as he speared his way through any remain glass ceiling. While Edge’s fans may have been disappointed he didn’t get to main event this show or work in a world title match, there’s some solace in knowing he would spend four out of the next five WrestleManias—four out of his last five ‘Mania matches—in world title scenarios either as the defending champion or a challenger.

#3. Brock Lesnar Ends the Streak at WrestleMania 30

I had a difficult time figuring out how to rank the end of the streak. On one hand, it’s not a moment I agreed with at the time, nor one that I completely condone in hindsight (though I do understand it better given Undertaker’s increasingly part-time status with WWE in the years to follow, and the monster push Brock Lesnar was in line for). On the other hand, this moment was huge in terms of shock value and historical importance as, after winning all twenty-one of his preceding WrestleMania matches, The Dead Man finally dropped one to The Beast Incarnate.

This moment is limited, too, by a lackluster build to the match, and an underwhelming match itself (purportedly due in part to The Undertaker legitimately suffering a concussion in the early going). For all of these shortcomings, though, I have concede that it’s a hard thing for WWE to legitimately shock its audience in this era, and this was an outcome that succeeded in pulling off an immense surprise and shifting the direction of the entire company. While I have long argued that Lesnar could have dominantly won the Andre the Giant Memorial Battle Royal at this show to similar effect for his big push, while protecting The Undertaker (not to mention adding more credibility to the ATGM brand from the beginning), I do understand that Lesnar winning that match may have been predictable, where as this finish was anything but.

Take the sight of even Paul Heyman looking shocked as he got in the ring to celebrate with Lesnar, and the unmistakable hush that fell over the live crowd in New Orleans, and you have an absolutely unforgettable, if imperfect moment in WrestleMania history.

#2. Shawn Michales Says, “I’m sorry. I love you.” at WrestleMania 24

It’s rare for wrestling to provoke conflicting emotions or draw a tear from its more jaded fans. In 2008, the company hit its stride in offering Ric Flair a farewell tour befitting his legendary run as arguably the greatest professional wrestler of all-time. Yes, Mr. McMahon imposing that the next time Flair lost a match he had to retire was a bit of a contrivance, but it set him up for good matches over the months to follow opposite the likes of Mr. Kennedy, MVP, Mr. McMahon, and others. It all came to a climax with Flair’s final match under the WWE banner, one last four-star-plus classic with Shawn Michaels.

The match itself was objectively quite good, but capped by a moment that summed up Flair’s legacy and his special relationship with Michaels as a creative influence and as a personal friend. As Flair refused to stay down, all but begging HBK to hit him with his best shot, Michaels mouthed what many-a-fan may have been thinking as they saw Flair on his very last legs: “I’m sorry. I love you.” He proceeded to nail Sweet Chin Music and score the pin.

There’s a fair argument this match, and more particularly this moment, should have ended WrestleMania 24, but WWE went a more conventional route with a world title match (not to mention a less conflicted happy ending) wrapping up the show. If they were concerned that trusting Flair to live up to the hype in the main event was a gamble, they probably shouldn’t have bet against Naitch. While he would go on to have other matches on smaller stages, this was his last match on this scale, and it was befitting his legend.

#1. Daniel Bryan Reigns at WrestleMania 30

From summer 2013 to spring 2014, a strange dynamic took shape in WWE. While Roman Reigns was lurking as a likely chosen one for the next generation, Randy Orton was positioned as the top dog in the company as a heel world champ, and Batista returned, immediately won the Royal Rumble, and looked to be cast as the conquering hero at ‘Mania.

And the fans rejected it.

Maybe, if there hadn’t been a compelling alternative, and Batista were supplanting John Cena as the top face, and particularly with the void CM Punk left behind, fans would have accepted The Animal on top. In the interim, however, Daniel Bryan had won the hearts and minds of a large swathe of the audience. Some claim WWE had a master plan all along, and Bryan was always destined for WrestleMania glory. Whether that’s true or not, Bryan reigning supreme come WrestleMania 30 sure didn’t feel like a foregone conclusion to most fans over the year leading up to the big show.

But there Bryan was. He kicked off the wrestling at ‘Mania with a four-star-plus encounter, pinning Triple H clean to win his way into the main event. From there, he made Batista tap out to cap an excellent Triple Threat between them and Randy Orton and close the show celebrating with this family, championship belts held over his head, as confetti rained.

For the great wrestling, the sweet vindication of Bryan reaching the top of the mountain, the bittersweet knowledge that he’d retire before reaching these heights again, and the far sweeter circularity of Bryan getting cleared to return in time for ‘Mania in New Orleans this year, this moment is my pick for the best of WrestleManias 21-30.

Which moments you add to the list? John Cena making Triple H tap at WrestleMania 22, Cesaro bodyslamming The Big Show to eliminate him from the first ATGM Battle Royal at WrestleMania 30, and an esoteric personal favorite of John Morrison’s ladder-assisted moonsault at WrestleMania 24 were my top runners up. Let us know what you think in the comments.

Read more from Mike Chin at his website and follow him on Twitter @miketchin.