Ranking the 20 Most Unforgettable Moments of WWE WrestleMania's Last 20 Years

Over the last two decades, WWE fans have watched WrestleMania evolve into a show as much about its moments as the actual wrestling.

A five-star classic is great, but did it make the members of the WWE Universe feel like the coronation of a new champion, the end of a streak, the retirement of a legend or the rightful ascension of women to the main event?

Those magical instances became the defining element of the biggest show of the year in the second half of the event's four decades and these are the most unforgettable moments from that span.

20. Shane McMahon's Leap of Faith (WrestleMania 32)

Shane McMahon has a long history of taking big chances in high-profile matches, so when it was announced he would battle The Undertaker in his first match back in nearly a decade, fans expected something big.

And he delivered.

With The Phenom sprawled across an announce table, McMahon climbed to the top of the cage, blessed himself and jumped off with an elbow drop attempt. His opponent moved and Shane-O-Mac crashed through the table, essentially ending his night.

Undertaker would win the match moments later, but McMahon had another in a long line of highlight-reel dives to add to his collection.

19. Money in the Bank (WrestleMania 21)

The brainchild of Chris Jericho when he, Edge, Christian, Kane, Shelton Benjamin, and Chris Benoit were left without anything of substance to do at the 2005 event, Money in the Bank was such an instant hit at WM21 that it became a signature piece of the WWE calendar in the years that followed.

On that night in Hollywood, The Rated-R Superstar bested the field, bashing Benoit's injured left arm with a chair and retrieving the briefcase, guaranteeing him a title opportunity he cashed in to become WWE champion 10 months later.

Today, the MITB ladder matches are such a popular part of WWE that an entire premium live event is dedicated to the match type and is among the most anticipated shows of the year.

18. Shawn Michaels' Last Ride (WrestleMania 26)

On the heels of an all-timer the previous year, a desperate Shawn Michaels sought one last chance to dethrone The Undertaker, but he had repeatedly found his challenge denied.

When he finally screwed The Deadman out of the World Heavyweight Championship at Elimination Chamber, he found himself on a collision course with his rival.

There was one catch, though: Michaels would have to retire if he lost at WM26.

For the second consecutive year, the legendary competitors tore the house down, this time live in Phoenix. HBK fought to preserve his career while The Deadman battled to keep his streak alive.

As history tells us, Undertaker survived by delivering one last Tombstone to a defiant Michaels.

A post-match show of respect ensued before HBK took one last walk up the aisle, waving goodbye to the fans.

17. A Red-Hot Spear (WrestleMania 22)

The escalating rivalry between Edge and Mick Foley led to the two future Hall of Famers squaring off in a Hardcore match at the 2006 event at All State Arena in Chicago.

One of the most anticipated bouts on the card, there were lofty expectations that two of the most fearless Superstars in WWE history would do something to reaffirm their legacies and steal the show.

Late in the match, Lita caught Foley with a low blow via barbed-wire baseball bat and proceeded to douse a table in lighter fluid before setting it ablaze. Seconds later, Edge took off across the ring and delivered a jaw-dropping Spear that sent him and The Hardcore Legend crashing through the table and to the arena floor.

His arm trembling from the heat, Edge draped it over Foley and scored the biggest win of his career while simultaneously providing his former mentor the WrestleMania moment that had long eluded him.

16. The Last Ride (WrestleMania 36)

Amid the COVID-19 pandemic in 2020, WWE turned to cinematic pro wrestling to make up for the lack of attendance at WrestleMania 36 as The Undertaker battled AJ Styles in a Boneyard match.

Taking place at a Florida graveyard, the bout was shot like a movie, with more emphasis on vocals, facial expressions and visuals than in a typical pro wrestling contest.

Widely praised for blending physicality with superb production, the match won several Match of the Year awards. It is most known today, though, as the last ride for The Undertaker.

The legendary competitor would never wrestle again, content with how his match against one of the best in The Phenomenal One had turned out.

After years of chasing that last great match, Undertaker achieved it and rode off into the sunset. He officially retired The Deadman once and for all at Survivor Series seven months later.

15. Battle of the Billionaires (WrestleMania 23)

In 2007, Donald Trump and Vince McMahon bet their hair in a so-called Battle of the Billionaires that attracted mainstream media attention and reintroduced WWE to pop culture for the first time in what felt like an eternity.

The megalomaniacs bet that their hand-picked Superstar would beat the other's, with the losing billionaire having their head shaved.

Bobby Lashley represented the future U.S. President while Umaga stood in for The Chairman of the Board. With "Stone Cold" Steve Austin officiating, it was Lashley who emerged victorious before joining Trump and Austin in shaving McMahon's head.

Circumstances beyond the squared circle have dampened the moment in hindsight, but there is no denying the impact it had, as WM23 would reign as the king of WWE pay-per-view buys until a certain "Once in a Lifetime" showdown broke that record five years later.

14. The Hardy Boyz (WrestleMania 33)

Matt and Jeff Hardy had spent eight years away from WWE by the time WrestleMania 33 rolled around, so it was a major surprise when The New Day informed Enzo Amore and Big Cass, Karl Anderson and Luke Gallows, and Cesaro and Sheamus they would be the fourth team in a ladder match for the Raw Tag Team Championship.

The crowd in Orlando greeted the returning innovators with the loudest reaction of the night and one of the great pops in 'Mania history.

Their excitement and overwhelming joy was only enhanced when the brothers won the gold.

13. A Story Unfinished (WrestleMania 39)

It seemed a foregone conclusion that Cody Rhodes would roll into WrestleMania 39, end Roman Reigns' three-year run atop the WWE and become the unquestioned face of the company in the process.

Things did not quite go as fans had envisioned, though, leaving the WWE Universe stunned when Solo Sikoa blasted The American Nightmare with the Samoan Spike, setting him up for a Spear from The Tribal Chief.

It was an unforgettable moment for the wrong reasons, with most fans expressing genuine frustration and anger at the outcome. It was meant to be a coronation for Rhodes, they believed, and backstage politics had to have played a role in the finish.

Or so they thought.

As it turned out, there were bigger plans in store for both men, even if they may have hit a bump or two in the road on the way there.

12. Bianca Belair and Sasha Banks Make History (WrestleMania 37)

Bianca Belair and Sasha Banks became the first two Black women to compete in a main event of WrestleMania when they took to the squared circle in 2021 for the SmackDown Women's Championship.

In one of the best matches of the night, they had fans on the edge of their seats, waiting to see who would secure the victory on the grand stage in Tampa, Florida.

It was ultimately Belair's night as she whipped The Legit Boss with her braid, sending a loud crack throughout the night sky, and delivering the Kiss of Death for the pinfall victory and her first championship on the main roster.

It was the start of an unbeaten streak for Belair at the event and a run that would eventually establish her as one of the legit top-line competitors in WWE.

11. YEStleMania (WrestleMania 30)

WrestleMania 30 was more affectionately known as YEStleMania, a culmination of Daniel Bryan's journey to the top of the company, despite several instances of WWE officials doing everything they could to resist it.

His connection with the audience was too strong, though, and his popularity became a runaway train that no one in the company was equipped to stop.

First, Bryan had to defeat Triple H in the opening contest to prove his worth. Then, in the night's main event, he fought through a rib injury caused by The Game to defeat Randy Orton and Batista in a Triple Threat for the WWE World Heavyweight Championship.

Bryan celebrated amid confetti and pyro as the show went off the air, concluding one of the unlikeliest journeys to the top of pro wrestling's most prominent promotion.

10. The Greatest Match of All Time (WrestleMania 25)

Shawn Michaels vs. Undertaker in 2009 at WrestleMania in Houston may forever be the greatest match of all time.

That sounds like hyperbole, but when taking into consideration the legacies those two Superstars had built for themselves, the expectations fans had when it was revealed that they would compete against each other and the stage it came on, the significance of what they were able to do that night is that much more impressive.

For 30 minutes, the grizzled veterans of a bygone era took fans from around the globe on a roller-coaster ride of emotions. Dramatic near-falls threatened Undertaker's unbeaten streak while fans of Michaels gasped any time he found himself in the clutches of The Phenom.

Ultimately, Undertaker caught Michaels mid-moonsault, drive him into the mat with a Tombstone and maintained his streak, but not before the Hall of Famers rewrote the history books and left everyone asking if they had just delivered the finest match of all time.

9. 'I'm Sorry. I Love You' (WrestleMania 24)

With Ric Flair's legendary career on the line, The Nature Boy and Shawn Michaels squared off in Orlando in 2008, in what was one of the most emotionally charged matches in WrestleMania history.

Flair turned back the clock once more for another performance symbolic of the epic encounters that had captivated fans throughout the territories through to WWE.

Feeding off the fans, the veteran took the fight to Michaels, refusing to let his biggest fan take his career from him...until he had no fight left.

Late in the match, an exhausted Flair staggered to his feet with his fists balled. Michaels looked across the ring at the man who inspired him and said: "I'm sorry. I love you," before delivering the Sweet Chin Music that ended The Nature Boy's run as one of the greatest of all time.

The emotion of the crowd and the spotlight shone on Flair made the moment truly unforgettable, even if he did find his way back into the squared circle for other promotions eventually.

8. HERstory in the Main Event (WrestleMania 35)

The 2019 show was a memorable one for a number of reasons, not least of which was the history made in the final match of the evening.

For the first time, women competed in the main event of WrestleMania as Charlotte Flair and Ronda Rousey defended the SmackDown and Raw Women's Championships, respectively, against Becky Lynch in a Triple Threat Winner Takes All match.

From Rousey entering to Joan Jett playing "Bad Reputation" live to Flair arriving via helicopter and Lynch's monumental run as the most over Superstar on the roster, the stage was set for the biggest match in the history of women's wrestling.

The competitors did not disappoint, delivering an action-packed headliner that concluded with Lynch pinning Rousey and capturing both titles, paying off her grueling rise to the top of the industry.

7. End of an Era (WrestleMania 28)

Michaels, Triple H and Undertaker spent four consecutive WrestleManias embroiled in a layered storyline that built from year-to-year, culminating in 2012 at WrestleMania 28 in an "End of an Era" Hell in a Cell match in which The Game would try one last time to put a blemish on The Deadman's unbeaten record at the event.

Making matters even more dramatic was that HBK would be the guest referee for the match, leaving some to wonder if he would screw The Phenom over for retiring him two years earlier.

He did not, but there was a crowd-popping Sweet Chin Music that resulted in the most dramatic near-fall of the night.

Instead, Michaels was mostly impartial and counted the three when Undertaker delivered one last Tombstone Piledriver to Triple H, advancing his unbeaten streak to 20-0 and bringing to a close an entire era of WWE.

6. Cody Rhodes Comes Home (WrestleMania 38)

Six years after leaving WWE, embarking on a journey of self realization and growth throughout the independents and co-reating All Elite Wrestling, Cody Rhodes returned to WWE in April 2022 at WrestleMania 38.

The surprise opponent for Seth Rollins, he entered AT&T Stadium to a deafening ovation and created an instant classic WrestleMania moment. The match with The Visionary was not too shabby, either, and kicked off a trilogy that would culminate inside Hell in a Cell a few months later.

The homecoming of a WWE original and second-generation star overshadowed everything about that weekend's massive event, including the in-ring return of Steve Austin, who beat Kevin Owens in a fine match in its own right, and immediately established Rhodes as the face who would lead WWE into a new era.

5. Once in a Lifetime (WrestleMania 28)

Real-life tension spilled onto the screen in the lead-in to WrestleMania 28, where John Cena and The Rock would compete in a battle of icons dubbed "Once in a Lifetime."

Though that tagline would not hold up thanks to the rematch that occurred a year later, it was a hotly anticipated match between top stars of different generations, enhanced by the verbal blows they took at each other on the road to the showdown.

With the fans in Miami solidly behind The Rock, they watched as The Great One capitalized on a moment of hubris out of Cena, delivered a Rock Bottom and scored the win in his first WrestleMania match in eight years.

The sight of a dejected Cena watching from the stage remains one of the most enduring images from a show that features plenty of them.

4. KofiMania (WrestleMania 35)

Kofi Kingston paid off one of the unlikeliest journeys to the top of WWE in 2019 by defeating Daniel Bryan and winning the WWE Championship, as the culmination of a movement known simply as "KofiMania."

Fans demanded Kingston's push and were repaid with one of the most joyous and historic moments in WrestleMania history.

Not only had a hard-working star, who was loved and admired by the fans, just won the top prize in the company, but he was also a Black man, standing victorious on the grandest stage in the sports, holding championship gold that had been denied to so many others.

There is no better encapsulation of what the moment meant to other Black athletes than the video of MVP and Shad Gaspard's reaction to Kingston's win.

3. The Heist of the Century (WrestleMania 31)

The greatest cash-in in WWE history came at the conclusion of the WrestleMania 31 main event, when Seth Rollins rushed the ring in the middle of Roman Reigns vs. Brock Lensar for the WWE Championship, handed over his Money in the Bank briefcase, and officially joined in, making it a Triple Threat.

Moments later, he narrowly escaped an F-5, thanks to a well-timed Spear from The Big Dog, and delivered a Stomp to his former Shield teammate to win the title and abscond with it up the ramp, where he held it high overhead amid a dazzling pyro display.

It was the most unexpected ending in 'Mania history to that point and one that generated much excitement and intrigue at a time when those words simply were not associated with the WWE product.

It also firmly established Rollins as one of the top stars in the company, a spot he still holds a decade later.

2. Story Finished (WrestleMania 40)

There was a point when it seemed Cody Rhodes may not finish his story and win the Undisputed WWE Championship as expected.

The return of The Rock muddied the waters, but the fans' unwavering support of Dusty Rhodes' youngest son forced WWE to abort plans for a showdown between Reigns and The Great One and go back to the original expectation of Rhodes vs. Reigns.

It was the right call as fans packed Philadelphia's Lincoln Financial Field to watch as The American Nightmare countered interference from Jimmy Uso, Solo Sikoa and Rock with assistance from Jey Uso, John Cena and The Undertaker to finally down The Tribal Chief, win the title and usher in a new era in WWE.

While there may be a bit of recency bias at play, one would be hard-pressed to find a more meaningful moment given what it meant to WWE at its hottest period in decades and for the fans who had watched The Bloodline story unfold over the past four years.

It was a perfectly executed Match of the Year candidate, and one of the defining moments in WrestleMania's long history.

Still, one moment tops it as the most unforgettable in show history.

1. 21-1 (WrestleMania 30)

It couldn't have been, could it?

It was the thought running through the minds of every fan as they sat dumbfounded in the immediate aftermath of the referee's count: On the grandest stage, the idiot smacked the mat three times and awarded Brock Lesnar the match against The Undertaker.

What a botch.

Except, it wasn't.

Lesnar had defeated The Deadman, ending his streak and erasing 21 years of dominance at The Showcase of the Immortals. The graphics that went up around the Superdome in New Orleans confirmed as much.

It was a moment of pro wrestling infamy, one in which every fan knows where they were when it happened. Sports Illustrated, CNN, NBC News and more mainstream outlets covered it as if it was a legitimate sports outcome. Social media buzzed.

It was so inconceivable that there are still fans to this day who believe the official slipped up, counted three and everything after has been an attempt by WWE to cover it up.

It wasn't, though, and controversy still surrounds the subject, with Undertaker recently revealing he did not find out about the decision until the day of the event.