Showstopper: Shawn Michaels and His 10 Greatest Wrestlemania Matches

He has gone by many nicknames. The Heartbreak Kid. The Main Event. The Icon.

But when it comes to the Wrestlemania event, no nickname better suits Shawn Michaels than "The Showstopper."

He has provided the fans of World Wrestling Entertainment and the entire world of sports-entertainment matches and moments that will live forever in pro wrestling lore. His name is as synonymous with the event as Hulk Hogan, Stone Cold Steve Austin, The Rock, Triple H, and The Undertaker, yet his matches have taken on lives of their own.

It was almost a given every year that, during "match of the year" conversations, Shawn Michaels' Wrestlemania match would be near or at the top of the list of discussion. As we head into the first Wrestlemania event since Shawn's retirement one year ago and his upcoming Hall of Fame induction, let us take a look at the 10 greatest matches of the legendary performer's career.

Two of the industry's all-time great in-ring performers squared off on April 3, 2005 in what many considered a dream match. Other than the legendary Bret Hart, Shawn Michaels had long been considered the cream of the crop in terms of in-ring abilities and his pension for crafting excellent masterpieces of professional wrestling. In 1998, however, Michaels suffered a near-crippling back injury that seemingly prematurely ended his career.

It was during his absence, in late 1999, that young, former amateur wrestler and 1996 Olympic Gold medalist Kurt Angle made his debut in WWE.

Angle, alongside Chris Jericho, Chris Benoit and Eddie Guerrero, ushered in an era of mat-based, technical wrestling that could conceivably replace the workmanship of someone like Michaels. Soon, Angle became the face of the in-ring work professional wrestling was built on.

No matter the opponent, no matter the consequences, Angle could be guaranteed to turn in one of the best, if not THE best, match of the night. His matches with men like the aforementioned Jericho, Benoit and Guerrero, young stars like Edge and John Cena, and newcomers like Rey Mysterio are still looked back upon and remembered fondly. But Angle's reputation would soon face a stiff challenge in the form of the returning Shawn Michaels.

Michaels' return was a critical success. Despite a four year layoff and virtually no ring work from 1998-2002, Michaels had come back and was arguably better than ever. Gone were the unnecessary high spots and in their place was a smarter, more psychology based style, not unlike that utilized by Angle. Fans clamored for the chance to see the two ring generals square off in a match that would revolutionize what could happen when two highly skilled, intense in-ring competitors met for an epic battle.

It would not be until three years after Shawn's return, in 2005, that the fans would be rewarded for their patience.

The match was phenomenal, a clash between two warriors on the biggest stage of them all. In front of a Hollywood crowd and on a show dubbed "Wrestlemania Goes Hollywood," Michaels and Angle proved that no matter how many celebrities are in attendance and no matter how much emphasis is put on the glitz, glamour and spectacle of Wrestlemania, great wrestling will always shine through.

Each man pulled out all stops, wanting to prove to the other that they were the better wrestler. In the end, Angle pulled out what many consider an upset victory, making Michaels tap out to the ankle lock at approximately 27:00.

The reason the match is not further up the list is two-fold. First, as great a match as the Wrestlemania contest was, many consider their match at the Vengeance pay-per-view roughly three months later its superior. The rematch such a short period of time later really lessened the impact of the original. Second, the ascension of Batista and John Cena, as well as the birth of the Money in the Bank ladder match, ultimately and unfortunately overshadowed the in-ring classic.

If ever there was a better example of the master of the art of professional wrestling Shawn Michaels really is, it was this match. For the first time in over a decade, Shawn was not on the receiving end of pressure to have the best match at Wrestlemania. The in-ring work was being placed on the back burner in favor of story. There were no expectations that the match with the owner of the company would even compare to HBK's previous Wrestlemania classics, let alone one day be listed amongst them.

What resulted was a key piece of evidence in the argument in favor of Michaels' place atop the list of "best wrestler ever."

In December of 2005, Shawn insulted McMahon, telling him to grow up and get over the "Montreal Screwjob," in which McMahon screwed the departing Bret Hart out of the WWE Championship in front of a live audience in Montreal, Quebec, Canada and hundreds of thousands more watching at home on pay-per-view.

As a result, McMahon set out to make Michaels' career a living hell, a feat he accomplished for several months. Then, just as Michaels appeared to be gaining the upper hand, McMahon introduced the freshly debuted Spirit Squad, a group of young, twenty-something male cheerleaders looking to make an impact in the business. Eventually, Michaels once again found himself on the receiving end of the numbers game.

Wrestlemania 22, in Chicago, Illinois, was set to be the climax of the intense rivalry between Michaels and McMahon. In what was billed as a No Holds Barred match, it appeared as though Michaels would dominate and destroy the CEO of the WWE. Breaking the enlarged replica of McMahon's Muscle and Fitness magazine cover over Vince's head, Michaels looked poise to walk away from Wrestlemania 22 with an easy victory.

Then, the cheerleaders struck.

The Spirit Squad created a sense of vulnerability for Shawn. The iconic performer was once again the victim of a beat down. It wasn't long before Michaels made his comeback and was able to clear the ring of the Spirit Squad, subdue an interfering Shane McMahon and finish off Vince McMahon with a vicious diving elbow through a table and some stiff Sweet Chin Music for the win. The hero stood tall while the villainous McMahon, his head bloodied and strapped to a stretcher, flipped the bird in the direction of his foe.

The match, while not living up to the other in-ring performances on Michaels' Wrestlemania resume, belongs on this list because it is simple storytelling at its best. For months before this match, Michaels was poked, prodded and tormented by his boss. McMahon had endless resources to harm Michaels and mess with his career and at Wrestlemania, the storyline was paid off in grand fashion as Michaels brutalized, bloodied and defeated his evil rival.

Michaels took McMahon by the hand and guided him to the greatest performance of his career. As spectacular a character as the Mr. McMahon character was during the Attitude era and as entertaining as his matches with the likes of Stone Cold, The Rock and Triple H had been, no performer had been able to get the quality performance out of Vince as Michaels was able to in Chicago at Wrestlemania.

If anything, the match proved that the test of a wrestler's greatness is not how great a technical masterpiece a match is, but whether or not the fans bought into what was going on, if it elicited the response it was intended to and if the story was properly paid off. The Michaels-McMahon match at Wrestlemania 22 was a masterpiece of performance art in terms of the professional wrestling business and more than deserves its place on this list.

Rumors had been flying rampant through most of 2007 and early 2008 that Vince McMahon was looking to end Ric Flair's in-ring career and continue to employ him as an ambassador for World Wrestling Entertainment. Flair, considered by many to be the greatest wrestler of all time, was clearly on his last legs and the in-ring talent he prided himself on employing had now been reduced to a series of signature spots and crowd-pleasing mannerisms.

So the idea was hatched for Flair's retirement match to occur at Wrestlemania, against the one man who had openly admitted to idolizing Flair and mimicking him as a youngster growing up in Texas. Shawn Michaels, largely considered one of the two best workers in the nineties and probably the best in the 2000s, was selected to end Flair's career in grand fashion in front of 70,000 fans inside the Citrus Bowl in Orlando, Florida.

Flair became the focal point of the entire Wrestlemania weekend. Before even stepping foot in the Citrus Bowl for the huge event, Flair was inducted the night before at the 2008 Hall of Fame ceremony. During an event that saw the return of The Rock to WWE for the induction of his father and grandfather, Flair easily overshadowed "The Great One," delivering a phenomenal speech that left many of the current crop of WWE Superstars teary-eyed.

As the legendary career of "the Nature Boy" made its way down the home stretch, the pressure on Shawn Michaels to help give Ric a fitting send-off grew immensely.

Both men made grandiose entrances. Michaels, with fireworks exploding around the top of the stadium, and Flair, sporting a spectacular new blue robe and with fireworks shooting into the night sky, were the epitome of true Superstars. Bigger than any other match on the card, the fans in attendance and those watching at home sat on the edge of their seats, each and every one of them emotionally invested in every single move, every single pin attempt and every single word exchanged between the two.

It appeared early in the match as if injury could send the contest spiraling into chaos. Michaels, attempting a top rope moonsault to the arena floor, landed sternum-first on the edge of the announce table. As he clutched his sternum, many were left to wonder what would happen to the match if Michaels was too injured to continue. But Michaels fought through the pain and continued the match.

An old-school battle of move and counter-move resulted, with Flair more than holding his own. In the end, Flair appeared to be resigned to the fact that his career was coming to an end and dared Michaels to finish him off. In an epic moment representative of the entire encounter and the storyline leading to the show, a reluctant Michaels visibly mouthed the words, "I'm sorry. I love you." He then loaded up and flattened Flair with Sweet Chin Music, covered him and ended his thirty-plus year career.

Ric Flair chose Shawn Michaels as his last opponent (before the ill-advised TNA run that began in January of 2010) and it proved to be a wise choice. With Flair in the physical shape and his wrestling skills more than diminishing, Shawn may have been the only performer talented enough and capable enough of giving Flair the quality of match he deserved on his last night in the ring. Flair held his own, performing at a level not seen from him since the mid-nineties in WCW. But Michaels guided Flair to a match many considered the most emotional in the history of the event.

Ten years after one of his most influential Wrestlemania bouts in the "World's Most Famous Arena," Shawn Michaels returned to Madison Sqaure Garden for Wrestlemania XX. Upon returning to the ring in August of 2002, Michaels immediately set his sights on former friend-turned-heated rival, Triple H. For the better part of sixteen months, the two major Superstars did battle with one another in several barbaric matches.

At the 2004 Royal Rumble event, the two fought a bloody, brutal Last Man Standing match that resulted in no definitive winner. Many were left to wonder when the issues between the two would end.

Also at the 2004 Royal Rumble, Chris Benoit pulled off a feat only accomplished by one other man. Starting the Rumble as the No. 1 participant, Benoit lasted over an hour, eliminating the Big Show and earning the right to challenge for either the World or WWE Championship at the biggest show of the year. The next night on Raw, it became evident that Benoit had targeted Triple H. He announced his plan to challenge HHH for the World Heavyweight Championship at the 20th installment of Wrestlemania.

But Michaels would soon interject himself into the match, signing a contract that would make the match a triple threat, the first time a three-way main event concluded the "Showcase of the Immortals."

What occurred on March 14, 2004 was not just one of the best triple threat matches of all time, but perhaps the greatest Wrestlemania main event of all time. For 24 minutes, Michaels joined HHH and Chris Benoit in crafting a masterpiece contest that saw all three come close on several occasions to capturing the gold and leaving Wrestlemania as the head honcho on the Raw brand.

In the end, Michaels was tossed out of the ring, leaving Benoit to counter a Pedigree attempt from "The Game" with a Crippler Crossface, forcing the title-holder to tap out. Benoit stood tall in the center of the ring as Wrestlemania 20 came to a close, his family surrounding him in a moment that would—for all the wrong reasons—be played for the whole world to see a mere three years later.

Despite the undeniable quality of the match and its status as one of the greatest in Wrestlemania history, the triple threat match remains low on this retrospective list of Michaels' 'Mania matches because of the unfortunate events that occurred in Benoit's life that have led to the match all but being erased from the history books.

While it still exists in DVD form and the fans that have seen the match remember its greatness to this day, the involvement of Benoit and the fact that it is the definitive moment in his career has tarnished the legacy of the match and forced WWE to treat it as though it never existed.

The Wrestlemania 23 match between John Cena and Shawn Michaels was unique in that it nearly did not happen. As a matter of fact, if it was not for a torn quadriceps suffered by Triple H two months before the big show, Cena and Triple H would have been the main event for the second consecutive year. Instead, with injury forcing "The Game" to the sideline, Shawn was once again thrust into the spotlight and trusted to add to his long string of all-time Werstlemania contests.

The question remained whether or not John Cena could keep up with and match Michaels' performances. The answer resulted in one of the best performances of Michaels' Wrestlemania career and, perhaps, one of the best of Cena's career as the top draw in the company.

Wrestlemania 23 had a whole different feel to it than the events in previous years. Media presence was high as millions around the world awaited the outcome of the "Battle of the Billionaires," which guaranteed a head shaving for either Vince McMahon or Donald Trump. It was also the 20th anniversary of the landmark event Wrestlemania 3, which set the indoor attendance record and remains, to this day, one of the greatest events in the history of the sport.

As if the added pressure wasn't enough, Michaels was given the task of helping Cena prove he had what it took to be the WWE Champion at the biggest show of the year and that he had the ability to perform at a high level on the WWE's biggest stage.

Cena and Michaels accomplished their goal, holding the crowd in the palms of their hands as they exchanged near falls, impactful hits and Michaels broke out his death-defying moonsault from the ring to the arena floor and onto Cena. At the end of the night, Cena left the magnificent Ford Field still WWE Champion after making Michaels tap out to the STF one year after doing the same to HBK's fellow DX teammate, Triple H.

In one match, Michaels gave Cena the notoriety and the legitimacy he needed to reach an all new level in WWE. Cena went from being the fan-hated, marginal in-ring worker to a polished pro who the fans may still not have liked, but now respected. For the first time, Michaels assumed the role of teacher and it was because of his lesson plan that Cena was able to grow and have the career he still enjoys to this day.

Here it is: the match responsible for several current WWE and TNA Superstars enjoying the success they are. The first nationally-televised ladder match featured two young, up-and-coming Superstars battling it out for the right to call themselves the undisputed Intercontinental Champion.

In the late fall of 1993, Shawn Michaels was suspended due to a questionable positive steroid test and as a result, he was stripped of the Intercontinental Championship. A battle royale netted two top contenders and, in the main event of the October 11 edition of Raw, Razor Ramon became the new champion. Upon Michaels' return, he argued that he was the true champion, having never lost the belt inside the ring.

At the Royal Rumble, Michaels tried desperately to cost Ramon the title to IRS, but Ramon was resilient and was able to retain his title. With two competitors feuding over who was the rightful Intercontinental title-holder, President Jack Tunney saw no other alternative but to put the title on the line in a brand new concept. For the first time ever (if you ignore the Michaels-Hart match from 1992), WWE fans would be treated to a ladder match. The new idea had fans excited for what would come.

Michaels and Ramon beat and battered one another with the heavy ladder. The match was completely different than any other in Wrestlemania history and the fans ate it up. They "ooooed" and "ahhhhed" with every crash of ladder into the flesh of the competitors. They watched in awe as Shawn made a relatively simple splash off the top of the ladder look like the most spectacular feat ever seen inside the squared circle.

It was the simplicity of the spots and the story told using the newly-introduced weapon that made the match as memorable and influential as it was. In the end, Razor walked away from the event with the Intercontinental Championship, but it was Michaels' performance that allowed WWE officials to have confidence in him that not only could he be a big-time performer on the Wrestlemania stage, but he also had the ability to carry the entire promotion at some point down the line.

That point would come two years later in another innovative match, one that would reap him the reward he so dreamed about as a child.

Much like the previously mentioned Michaels-Angle match at Wrestlemania 21, the Iron Man Match for the WWE Championship at Wrestlemania 12 was a celebration of outstanding in-ring product. In the three years following Hulk Hogan's departure from WWE, Shawn Michaels and Bret Hart revolutionized what professional wrestling was.

Gone were the days of large, steroid-injecting freaks whose size put them at the top of the card. Hart ushered in an era of the smaller, technical wrestler who could OUT WRESTLE his opponents and win championships as a result. Michaels benefited from Hart's success and soon allowed his in-ring abilities guide him to the top of the card.

1995 saw Michaels gain an all new fanbase, one that appreciated him for his outstanding technical abilities and his spectacular display of athleticism. While Bret Hart remained the most popular star in the company, Michaels quickly bypassed Diesel and moved into the No. 2 baby face position behind the Calgary native.

In November of that year, an injury angle was shot involving Michaels and Bret's brother Owen. The angle called for Shawn, who had been badly beaten in a very real fight with several men outside a bar in Albany, to come back too early and as a result, not be fully healed from the wounds. Owen Hart would execute an enzugiri in the contest that would cause Michaels to pass out in the center of the ring and need to be attended to by medics. A months-long stretch featured videos highlighting Michaels' career while the announcers were left to wonder whether or not the WWE fans had seen the end of HBK.

Those questions would be answered at the 1996 Royal Rumble event, where Michaels made his triumphant return and eliminated his best friend Diesel to win the match, earning a shot at the WWE Championship at Wrestlemania. But in February, Michaels would be faced with a challenge. He would put his Royal Rumble title opportunity on the line against Owen Hart, the very man who had put him on the shelf for such a long period of time in the first place. In a valiant performance, Michaels delivered Sweet Chin Music and secured his spot in the Wrestlemania main event.

When Bret Hart defeated Diesel in a Steel Cage match that same night, it became apparent that the Wrestlemania main event would feature the two best in-ring performers of the 90s doing battle for the WWE Championship. When interim WWE President Roddy Piper announced the match would be fought under 60 Minute Iron Man Match rules, the hardcore wrestling fans nearly exploded in anticipation.

The match was a display of technical masterpiece and unbelievable endurance. Both men countered several of the other's holds and looked to have the upper hand at several points in the match. Yet, despite the high impact of the strikes and the masterful use of the holds and counter holds, neither man could pin the other's shoulders to the mat, nor could they make them submit. As the clock rapidly approached the deadline, Michaels leaped from the middle rope and was caught by Hart, who locked him in a Sharpshooter. Michaels screamed in agony, but refused to give up.

As the clock struck the 60-minute mark, it became clear we were left without a winner. Hart left the ring, the WWE title draped over his shoulder, while an exhausted Michaels lay on the mat. Then, President Gorilla Monsoon made the decision: there must be a winner and the match would head into sudden death overtime.

Hart, incensed, returned to the ring, called for the bell and resumed his attack on Michaels. A mistimed charge into the corner, however, allowed Michaels to rifle off Sweet Chin Music. Hart fell to the ground, but Michaels could not capitalize. As both men made it to their feet, Michaels once again struck with his finisher, this time mustering up enough energy to fall on top of his respected rival. Michaels hooked both legs while the referee counted three and, in an instant, realized his boyhood dream.

Michaels celebrated while a dejected Hart made his way to the locker room.

The Iron Man Match was a turning point in Michaels' career. It took him from being a spectacular in-ring competitor to being the face of the company. He was now relied upon to put in the very same quality of work and performance he had in the Iron Man match every single night in arenas across the country. And he did. Whether or not the ego that resulted from his seemingly undying ability to have a great match with just about anyone put in front of him led to the attitude and behind the scenes issues that eventually resulted is another story.

This match, however, shot Michaels into the same atmosphere as the greatest professional wrestlers in history and really helped to shape his legacy.

The No. 3 match on this list stands as Shawn Michaels' last match. It was, perhaps, the most eagerly anticipated match in the history of Wrestlemania, even more so than Hulk Hogan vs. Andre the Giant at the third installment of the historical show. It was a match that sold the entire Wrestlemania XXVI pay-per-view event on its own and in the end, more than lived up to the hype.

One year earlier, Michaels and the Undertaker engaged in a match many considered the greatest in the history of the event. It was immediately deemed the "Match of the Year" and was universal in its critical success. WWE had no choice to recognize it as their Match of the Year in December of 2009 at the Slammy awards.

It was during his acceptance speech that Michaels announced that he wanted to challenge Undertaker to a rematch at Wrestlemania XXVI. He swore he could beat the "Dead Man" and end his unbelievable undefeated streak at the "Showcase of the Immortals." All he needed was for 'Taker to accept the challenge. The World Heavyweight Champion at the time, Undertaker refused, deciding to make Michaels earn the right to face him at the event.

After a failed run in the Royal Rumble, Michaels successfully changed Undertaker's mind, costing him the World Heavyweight Championship in the Smackdown Elimination Chamber match. The match was on and the fan anticipation for the match was at a fever pitch. The biggest question heading into the 26th edition of Wrestlemania was whether or not the two veterans would be able to top their previous performance.

Like the year before, Michaels and Undertaker put on a display of showmanship no one else on the card could match. In the main event, on the biggest stage in the sport, they had the crowd on the edge of their seats, each of the thousands in attendance gasping at every big move and false finish. And like the year before, Michaels came up short, once again etching his name on the long list of Undertaker's Wrestlemania victims.

In a rare break of character, "The Dead Man" embraced HBK in the ultimate sign of respect.

Michaels would make the long walk up the aisle, acknowledging the thousands that had filled the University of Phoenix stadium. A year later, he has upheld his promise never to wrestle again following his loss at Wrestlemania XXVI. He repeatedly confesses his love of retired life and is seemingly content not to wrestle again, spending time with his wife and children instead.

Shawn's storied and legendary career ended with a bang rather than a whimper. He did not stick around longer than needed and instead, rode off into the sunset with a performance arguably as good as any in his career.

Wrestlemania XIX saw Shawn return to the stage he had revolutionized. After a four year absence that saw Michaels reform his life, Michaels returned to WWE and immediately feuded with Triple H. Upon wrapping up the rivalry with his former friend, Michaels immediately entered an intense feud with the man who idolized him while growing up in Winnipeg, Chris Jericho. Chris not only wanted to beat Shawn Michaels at Wrestlemania, he wanted to prove he was a better wrestler.

In Jericho's words, "(he) stopped wanting to be the next Shawn Michaels and, instead, wanted to focus on becoming the first Chris Jericho." The stage was set for a match that had the internet fanbase salivating at its mere mention.

The two ring generals engaged in a phenomenal match that overshadowed every other on the card and once again reaffirmed the notion that wrestling could be as important as spectacle at Wrestlemania. Jericho countered HBK's arsenal with Michaels' own signature maneuvers. In response, Michaels wrestled a more basic, fundamental match, beating Jericho with a simple roll-up, rather than his patented Sweet Chin Music.

The match ranks this high on the list not only because of the pure wrestling contained within, but also because it was a showcase of Michaels' versatility. For the first time since the Wrestlemania XII Iron Man Match, Michaels was not left to carry an entire match on his back. He was not the focal point. The match was a showcase for Chris Jericho and Michaels more than proved he was able to play second fiddle and not steal the spotlight for himself, something others had doubted was possible.

Despite the loss, Jericho came out of the match looking significantly better than he had heading into it and as a result, became a bigger, more believable main event talent than he had already been. Michaels made that possible. The desperation roll-up win proved just how much of a challenge Jericho had proven to be and was a spectacular layer of storytelling on top of every other nuance in the contest.

It was Shawn Michaels' ability to play second fiddle, to dumb down his showmanship and skill set and to get someone else over without putting himself over that made his encounter with Chris Jericho at Wrestlemania XIX the epic clash it became.

Is it really a surprise? For the first time since the Rock vs. Hulk Hogan at Wrestlemania X8, a match was hailed as an instant classic, one that would go down in the annals of wrestling history as an all-time great. For the first time since the seven-minute stretch that concluded the 2007 Royal Rumble match, Shawn Michaels and Undertaker did battle in a one-on-one contest that would set the wrestling world on fire and shape the main event program for the next year's event.

There is no need to discuss the match in any sort of detail. Pro wrestling fans have undoubtedly seen the match, or at the very least highlights, and have bared witness to its greatness. On one night, in the home state of both competitors, everything went right. Every spot and every near fall kept the fans emotionally invested in the match, living off every move the world class entertainers executed.

Undertaker showed more emotion in the span of 30 minutes than he had in years. "The Dead Man" showed frustration and Michaels added his trademark never-say-die attitude, creating a sense of uncertainty not normally associated with 'Taker and his Wrestlemania Streak.

In the end, Undertaker once again proved why he was the most dominant Superstar in the history of the event and Michaels reaffirmed why he is considered "Mr. Wrestlemania." On the 25th anniversary of the event, Undertaker and Shawn Michaels showcased what the epitome of professional wrestling was and still is.

The match was a combination of spectacle and work rate, a rare modern-day masterpiece that immediately took its place among the Steamboat-Savages and the Hart-Austins. It saved a mediocre show and created fan anticipation for the inevitable rematch.

Perhaps it may be a case of hyperbole, but the match was a piece of modern artwork comparable to any other in any other medium, featuring two of the last of a dying breed.