Whether you like him or not, “The Heartbreak Kid” Shawn Michaels is one of the best performers in wrestling history. In his youth, he was a brash and cocky Superstar who could always back it up in the ring, and in his prime, he was celebrated for being able to get a good match out of any wrestler he faced, no matter who it was. After a back injury robbed him of several years and nearly his entire career, he returned to the ring a changed man, but still one of the absolute best wrestlers in the world. As a wily veteran, he continued to show that he could wrestle with the very best the business had to offer, and even carry the undeserving to the greatest matches of their careers. He even ended his in-ring career in 2010 while still, arguably, at the top of his game, choosing to go out with his head held high. Over a career that spawned more than thirty years, HBK had more than his share of spectacular matches, and limiting it to his ten best was a struggle of epic proportions, but somehow, we managed it.

10. vs Triple H, Unsanctioned Match, SummerSlam 2002

Due to a massive back injury suffered in 1998, Shawn Michaels’ wrestling career came to an end. He underwent spinal fusion surgery and retired to his home in Texas, and in the process, managed to overcome his longtime battle with substance abuse and turned his life around. And then, in 2002, he decided that he could have one more match, probably just to prove that he could. Best friend and D-X co-founder Triple H was hand-picked as his opponent, and an angle was created where Shawn tried to re-form D-X, only to have Triple H attack him. At SummerSlam, HBK’s return match took place, with an “unsanctioned” label because Michaels was technically no longer an active wrestler. What followed was one of the best “street fight”-style matches in the history of WWE, as both men threw everything at each other (likely because Michaels still believed this was his one and only match) in a display of two of the best workers in the business at the height of their game. Michaels emerged victorious, then disappeared again. However, the wrestling bug had gotten its teeth back into HBK, and thanks to an actual miracle that left doctors legitimately scratching their heads, Michaels’ back had apparently fully healed, and he went back on the road, wrestling for another eight incredible years.

9. vs Diesel, In Your House: Good Friends, Better Enemies 1996

For all that Kevin Nash has never been the best worker in the business (mostly because, as he has repeatedly pointed out over the years, a guy his size doesn’t have to be), when he wanted to, he could turn it on and hang with the very top wrestlers in the world. Such was the case in what would turn out to be his final match of his initial run in WWE, a Pay Per View main event against his close friend, WWE Champion Shawn Michaels. After a year as the blandest (and lowest-drawing) WWE Champion ever, Nash was refining the “tweener” role which would eventually define his career as one of the founders of the New World Order, still ostensibly a good guy, but with an edge that fans were latching onto. Knowing he was on the way out the door to WCW, and facing one of his best friends in the industry, Nash let it all hang out in this match against Michaels, who at that point was likely the absolute best wrestler on the planet in terms of wrestling skill, in a nasty and brutal Street Fight that many have called Nash’s best match ever.

8. vs Razor Ramon, Ladder Match, SummerSlam 1995

While their first match is one of the best matches in wrestling history (so obviously, we’ll get to it), the second one often gets overlooked. Literally added to the SummerSlam as a last-minute change in order to save a show that was not looking like it was going to be well-received (which is what happens when you headline a Pay Per View with Diesel vs King Mabel), Michaels and Ramon were being asked to replicate, and perhaps top, their star-making performance from just over a year earlier. As an added wrinkle, a stipulation was created where they were not allowed to use the ladder itself as a weapon, so both men settled for just using their bodies instead. It says a lot about the humble beginnings of the ladder match that the introduction of a second ladder into this match was seen as a massive innovation. While they didn’t manage to equal their Wrestlemania X match (which was a nearly impossible goal to being with), they certainly gave it their best shot, making this one, if not a forgotten classic, one that certainly doesn’t get as much recognition as it deserves.

7. vs John Cena, UK Raw, 2007

At this point, Shawn Michaels was running around with Triple H as a reunited D-Generation X, basically acting like a teenager in between having good tag team matches on the undercard. Meanwhile, John Cena was deep into the backlash against his character, leading to the mixed audience reactions that would stick with him to this day. And in fact, these two were not supposed to feud, as the original plan had been for Cena to face Triple H at WrestleMania in a rematch from the year before (and Cena was actually expected to lose that match). However, Triple H suffered the second massive quad injury of his career just before Mania, and Shawn Michaels stepped in to fill the void. After a great match at WrestleMania, Cena and HBK decided to follow that up by throwing time limits out the window and wrestled for nearly 60 minutes on a random episode of Raw emanating from London. It was one of the greatest matches in Raw history, not only because of the obvious skill level of both men, but because it was totally unexpected and a massive break from the typical Raw format (and to WWE’s credit, they continued to pretend as if the match would end any minute and promoted other upcoming matches on the show that would never happen).

6. vs Ric Flair, WrestleMania XXIV

Ric Flair might eternally be “The Man”, but by 2008, he was well past the point where anyone should getting into the ring on a full-time basis. A decision was made (some say Flair was forced into it, and on at least some level, he likely was), and it was announced that the next match which Ric Flair lost would be his last WWE match ever. Flair ducked and dodged for a few months, but as they often do in WWE, things finally reached their inevitable conclusion at WrestleMania, against Flair’s hand-picked opponent, Shawn Michaels. Was it the greatest wrestling match ever? No, the deterioration of Flair at that point was too great, even though he tried his damndest to summon up every bit of the Flair of yesteryear. But for sheer emotion and passion, and for seeing two of the very best squaring off one final time, there are few better matches that you will ever see, culminating in the five most memorable words in WrestleMania history: “I’m sorry. I love you.”

5. vs Bret Hart, Iron Man Match, WrestleMania XII

This match has received a ton of backlash as the years go by. Many say it was too long, that the first half of the match wasn’t very good, and that having only one fall for the entire match was unrealistic. And of course, die-hard Bret Hart fans thought the surprise “sudden death” finish was terrible and unsatisfying. In the years since, it’s been revealed that this match was affected by the political factors in play, as both men were already clashing behind the scenes, a rivalry that would play out both backstage and on TV over the next couple of years. The reason why there was only one fall, in fact, was allegedly because neither man trusted the other enough to not screw them over in a multiple-fall match, and the fact that neither seemed particularly interested in selling any offense for the first half of it was related to that as well. For all its faults, however, it is still the best match between two of the absolute best wrestlers on the planet, in their prime, caught up in a legendary feud that would end up defining, for good or ill, their entire careers. It is something that any wrestling fan should watch at least once in their lives.

4. vs The Undertaker, Career vs Streak, WrestleMania XXVI

Much like HBK’s ladder matches with Razor Ramon, we’re going to plead the old “their first match was better” excuse for this one (actually, you’ll find that we think there were two HBK-Undertaker matches better than this one). There is no doubt in our mind that this one had a much better build to the match, with an increasingly desperate Shawn Michaels trying to figure out a way to guarantee himself a second shot at the man he “knew” he could beat at WrestleMania. In the months before the match, Michaels went to some dark places, eliminating friends from the Royal Rumble, attacking authority figures, costing himself the WWE Tag Team titles thanks to his own mental distraction, and costing The Undertaker the World Heavyweight Title in a last-ditch attempt to force the Dead Man’s hand. While that last action succeeded, The Undertaker demanded that Michaels put his career on the line, which HBK readily accepted. And in that instant, even though the match itself was just as good as their first one a year earlier, a sense of inevitability crept in. By WrestleMania, fans were basically certain that they were watching Shawn Michaels’ last match, robbing the match of some of the intrigue found in the first one. But if you’re going to go out, losing to The Undertaker at WrestleMania in one of the best matches of your career isn’t the worst way to go.

3. vs The Undertaker, Hell in a Cell, Badd Blood 1997

We now enter a the top three matches, which we believe you could probably put in any order and still be correct, because for our money, these three matches are some of the best and most influential matches in the career of Shawn Michaels, as well as the history of WWE, and yes, even all of pro wrestling up to this point. This first one is the infamous first appearance of the legendary Hell in a Cell gimmick, created to keep Michaels and Undertaker contained after their previous PPV match (at Judgment Day 1997, which is also an underrated classic) ended in a chaotic brawl that emptied the locker room. This is, without question, one of the most brutal matches ever to take place in WWE, as both men beat the absolute hell out of each other, as blood flowed freely in the very early going. This match is also famous for the iconic debut of Kane, who appeared just as The Undertaker seemed ready to finish Shawn off for good, attacking his brother and allowing HBK to steal an incredibly fortunate pinfall, instantly establishing a character that would have a long and storied career lasting nearly two decades.

2. vs Razor Ramon, Ladder Match, WrestleMania X

Next, of course, we have the very first televised Ladder Match in WWE history, a gimmick with origins in Stampede Wrestling out of Calgary, which was introduced to the masses on the biggest stage, by two of the best workers in the company at the time. With both Michaels (who had originally been suspended and stripped of the belt) and Razor Ramon claiming to be the real Intercontinental Champion, this match was created in order to settle things once and for all. Expectations heading into this match were likely uncertain, after all, very few people had likely even heard of a Ladder Match at that point, and both Michaels and Ramon made sure to make the very first match of this type one that would be remembered forever. The pace was set early, as they traded high-risk moves and brutal shots with the ladder from the opening bell, crafting what many have seen as a nearly perfect match in the process. Given the general availability of ladders in modern matches, it’s hard to imagine that they crafted this entire bout using only a single one (although it ended up very much the worse for wear by the end, and was nearly rendered unusable before the finish). Over two decades later, this very first Ladder Match still holds up today, and is considered by mant to be the greatest Ladder Match of all time.

1. vs The Undertaker, WrestleMania 25

Ultimately, this match had to top the list. In every respect, it is the closest you will ever get to a perfect wrestling match. It involved two of the greatest wrestling talents the world has ever seen, two veterans with long careers who were considered by some to be the very cornerstones of WWE. And while the primes of their careers were long past, Shawn Michaels and The Undertaker had long ago replaced youthful enthusiasm with the tenacity and craftiness that age brings, using their combined knowledge and experience to create a match that played exactly to their combined strengths. And let’s not forget, even at that point in their careers, they were still considered two of the best workers on the planet. While the match itself lasted a full half hour, in the eyes of those watching it still wasn’t long enough. And while nobody truly believed that Shawn Michaels would end The Streak, this was possibly the first time since The Streak became one of the most important records in wrestling that it seemed like if anyone could legitimately end it, it would be HBK. Frankly, after Michaels failed to do so, The Streak matches at WrestleMania almost lost some luster, because if he couldn’t do it, it seemed like nobody on Earth could (which is why absolutely everyone was shocked when Brock Lesnar finally accomplished it several years later).