5 Timeless Shawn Michaels Matches Everyone Should Remember

Shawn Michaels is arguably one of the best wrestlers of all time. There are not too many wrestlers in the modern day and age who can match the sheer charisma and showmanship that the Heartbreak Kid brought with him to the ring.

While in his earlier WWE years, he was reportedly not too pleasant to work with, that did not stop him from making sure that the matches that he put on were not something that anyone could complain about. With hardly a single match of his entire life being a half-hearted effort, the history of matches for Michaels is like a look at the who's who of professional wrestling.

There are very few top stars from the Attitude Era that Michaels has not faced, and even if there are, he more than made up for it with those that he faced.

With Super Show-Down coming up, Shawn Michaels is set to be in Triple H's corner, when his best friend faces The Undertaker in the ring. This has led to rumours, that the Heartbreak Kid may indeed end up returning to the ring later this year, purportedly for a match against the Brothers of Destruction, while Michaels will team with Triple H to reunite D-Generation X.

Given the rise in rumours, it is time to take a look back at his career over the years and showcase 5 of his most timeless matches, which everyone should know about.

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#5 Razor Ramon (WrestleMania X)

Shawn and Razor innovated the Ladder Match

Razor Ramon's match against Shawn Michaels was one of those matches that went on to create history. Being that this is a list of some of the best matches the Heartbreak Kid took part it, it is safe to say all the other matches share this trait.

In 1994, after Shawn Michaels came back from suspension, he challenged Razor Ramon for the title that had been stripped off of him. He had his own version of the belt and was claiming to be the real champion.

With both belts hung over the ring, the two faced each other in a ladder match at WrestleMania. The match was one of the best of all time, and it is said to this day, that it inspired a whole new generation of wrestlers, as it revolutionized the match type.

The high-flying action of actually jumping off the ladder, and using it as a weapon, was not something which was so common back in the day. While since then there have been innovations, it is this bout between Ramon and Michaels at WrestleMania X that actually showcased what a ladder match could be.

#4 Bret Hart (Survivor Series - 1997)

Shawn and Bret stared on as the referee rang the bell

On the opposite side of the WrestleMania X match, which was and still is famous, this match against Bret Hart at the Survivor Series is one that lives in infamy.

The feud between Shawn Michaels and Bret Hart was one of the hottest things in WWE at that point, and the audience was eating it up. One of the reasons it was so convincing was that Bret actually did hate Shawn Michaels in real life.

While the two shared several significant matches together, including the one where Shawn won the WWE (then known as WWF) Championship for the first time.

However, this match is one, the importance of which cannot be understated, as it is one which is still talked about to this day. Bret Hart was leaving the company to join WCW. WCW and WWE were at war back then, trying to be the promotion that got the higher ratings. WCW was winning around this time, and several other high profile wrestlers had already made the jump to the rival promotion for the high pay they were offering, including Kevin Nash, and the aforementioned Razor Ramon.

Bret Hart was one of WWE's top wrestlers and was extremely popular with the fans. His leaving the company would have been something Vince McMahon frowned on under normal circumstances, but on top of that to put the cherry on the metaphorical cake, he was also the WWF Champion at the time.

When Vince asked him to drop the title to Shawn Michaels at Survivor Series, the day before his contract ran out, he refused. His hatred for Shawn would not allow him to do that, but at the same time, he was willing to vacate the title on the following night.

Vince had already had a bad experience with a champion leaving WWE, when Alundra Blayze, left the company to join WCW, and once there, threw their Championship in a trash can, insulting her previous company.

To prevent just such an incident, Vince instead made sure that Bret would be dropping the belt to Shawn at Survivor Series, whether he wanted to or not. During the match, when Shawn put the Sharpshooter on Bret, Vince ordered the referee to ring the bell, despite the fact that he had not tapped. Just like that, Shawn was awarded the Championship.

The audience in Montreal was incensed to see Bret treated like this, and while Shawn beat a hasty exit the audience pelted the ring with trash, showing their displeasure at such an underhanded tactic. Bret demolished the side of the ring, and later reportedly punched Mr McMahon, before going off to join WCW.

Shawn and Bret made up on Raw years after the incident in the late-2000's, but the Montreal Screwjob is an unforgettable, and indelible part of wrestling history.

#3 Triple H (SummerSlam 2002)

Triple H and Shawn's rivalry is one that has gone down in history

Back in 1998, during a Casket Match with the Undertaker, Shawn landed badly when he was thrown out of the ring. His back hit the edge of the Casket, effectively injuring his back extremely seriously. He had two discs herniated in the fall and continued to wrestle despite it through tremendous pain. He would go on to drop his Title against Stone Cold at WrestleMania that year, before retiring from in-ring competition.

He would continue to appear on television every now and again, but for all effects and purposes, he was leaving the ring behind. And he did, for four years.

In 2002, when Triple H came to Raw, it was Shawn Michaels who convinced him to join Eric Bischoff's brand. Unfortunately, the two got into an argument about Michael's role on the brand and eventually, this would to Triple H turning on him. He put Shawn face-first through a glass window of a car.

For the first time since retiring. Shawn Michaels agreed to make a return to the ring. He wanted an unsanctioned match against Triple H, and at SummerSlam, that's what he got. In possibly one of his best matches of all time, the Showstopper showed the world, and himself, that he still had what it took to compete in the ring.

A match full of chairs and high spots, no one had expected Shawn's comeback match after four years away from the ring to be what it was. Thankfully for him, he could still perform at the highest level, and despite the chronic back pain, would return to the ring to wrestle for another eight years.

It is worth mentioning, that in his four years away from the ring, Shawn had turned over a new leaf, and had taken a step away from the drug-addled human being that he had been, to embrace his new faith, and to take time for his family.

As a result, his second run in the company is seen by many to be his best run, as during this time he helped many other wrestlers to gain momentum by putting them over.

#2 Ric Flair (WrestleMania XXIV)

Shawn Michaels put away his hero, Ric Flair

By the time 2008 had come around, Ric Flair was a shadow of his former self. One of the wrestling greats, who had set records during his run in the wrestling business, Ric Flair was beloved by all. From the days of the wrestling territories to the Monday Night Wars, and finally in WWE, he had been front and center for most of the time.

But, in the recent years, the passage of time had caught up with him. He was no longer the wrestling legend of old, and he could not keep up in the ring. During this time, he wrestled a lot of matches, with a condition that any of them would be his last if he lost.

Finally, at WrestleMania XXIV, he faced Shawn Michaels. Shawn and Ric were good friends in real life, and the younger star was a huge fan and had great respect for the Nature Boy. It was one of those moments in wrestling where emotions were riding high.

In a sequence, that is still remembered by every fan of wrestling who watched it to this day, with Ric begging to be put away, Shawn lined up the Superkick. He mouthed the words, "I am sorry, I love you." and then, hit Ric Flair with a beautiful Sweet Chin Music. The pin. The 1... 2.... 3. That was it. Ric Flair's career was at an end.

Shawn hugged Ric, breaking down in tears, and then quickly left the ring, leaving him to savor his last moments in a WWE ring. The audience was crying, Ric was crying, and as Shawn walked away his tears were visible for all to see.

While Ric spoilt the point of this match later, wrestling in TNA for a brief period, at that moment there was nothing purer than what the audience had seen, as it showcased what wrestling was all about, captured in one small match.

#1 The Undertaker

The Undertaker and Shawn Michaels had one of the best matches in WWE history

The Undertaker and Shawn Michaels wrestled twice in the late 2000's, and on both occasions, it was special. They put on shows that no one other than them could have put on. While the first match, in WrestleMania 25 is considered by many to be the better one, for the sake of this article, we will be looking at when the two wrestling legends faced each other at WrestleMania 26.

At WrestleMania 25, despite all his efforts, Shawn had lost against the Undertaker due to one misstep. The loss ate at him throughout the year as he looked to regain his confidence and go about his business. As they headed towards the WrestleMania of next year, Michaels grew obsessed with his need to face the Undertaker one last time.

When the Undertaker refused, he decided that there was only one way to do it. The Undertaker was holding the World Heavyweight Championship at the time, so Shawn wanted to win the Royal Rumble to make his way to the Dead Man and use his Rumble win to challenge him for a Title Match.

However, despite dominating and lasting most of the match, with only a few minutes to go, he was eliminated. His disappointment at what seemed to be the only chance he had to reach the Phenom disappearing, Michaels sank to more nefarious means. During the Elimination Chamber match, he hid under the chamber floor, only to rise up when the Undertaker was least expecting it and hit him with a Superkick. In doing so, he handed the win to one of his biggest rivals, Jericho, but he was past all other rivalries.

Enraged, the Undertaker would accept Michael's challenge, but with something more on the line. In order to have the right to try and break the Undertaker's win streak at WrestleMania, Michaels would have to put his own career on the line. Shawn did so in a heartbeat.

Shawn Michaels faced the Undertaker in a match which no one had seen coming. No one had expected that the two of them would be able to pull of a repeat of their bout the last year, but that's exactly what they did. Shawn and Undertaker went back and forth, until no one knew who would be walking out the winner.

Finally, it was one small mistake by the Heartbreak Kid that saw him undone. He lost as the Dead Man pinned him again, and it was over. The career of Shawn Michaels, one that started with a Boyhood dream was gone in one of his most glorious matches of all time.

Now, Shawn Michaels may be set for a comeback, eight years after his retirement. His last match is one that cannot be bettered, but then again, this is the Heartbreak Kid we are talking about. With him, one can never tell.

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Seeing how there are only five matches in this list there are many more throughout Shawn Michaels' career which may have struck a chord with you. Which are your favorite matches of Michaels' career? Leave your thoughts in the comment section below!