The Definitive List of Must-Watch Matches from WWE Hall of Famer Shawn Michaels

Erik Beaston@@ErikBeastonFeatured ColumnistDecember 28, 2021

The Definitive List of Must-Watch Matches from WWE Hall of Famer Shawn Michaels

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    Credit: WWE.com

    Shawn Michaels is, arguably, the greatest wrestler of all time.

    What he has accomplished in the rings of WWE is second to none; the sort of mastery even the most recognizable stars in professional wrestling would be hard pressed to replicate. He is a virtuoso between the ropes, a storyteller of the highest degree.

    He is also a trailblazer, introducing different match types to the masses and setting the bar incredibly high for those who follow him to eclipse.

    Perhaps that is why coming up with 10 matches that most define him and his career was so damn difficult.

    Yet, here they are, ranked according to overall quality and, in some cases, historical significance.

10. WrestleMania XII vs. Bret Hart

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    It took a considerable amount of faith in both Michaels and Bret Hart for Vince McMahon to give them 60 minutes on the biggest show of the year, especially when hour-long Broadways were not the sort of match the more entertainment-based product had routinely presented.

    WWE was the land of giants, home to larger-than-life characters whose style could rarely keep the attention of the audience for that long.

    Hart and Michaels were different, though. They championed an athletic style in which technical wrestling took precedent.

    For 60 minutes, they took fans in Anaheim on a dramatic, emotional rollercoaster ride. When they remained tied at zero falls apiece, they entered sudden-death overtime. Michaels emphatically ended the match just under two minutes in with Sweet Chin Music. It delivered Michaels his first world title and established him as the face of the company. 

    McMahon's exclamation that, "the boyhood dream has come true!" added exponentially to the moment, making it one of the most enduring in the long history of WWE.

9. WrestleMania XXVI vs. The Undertaker

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    Michaels and The Undertaker tore the house down in Houston in 2009 with an all-timer (more on that in a minute), so it made sense that WWE would want to run the match back again a year later in Phoenix, this time with added stakes.

    No longer was it just The Phenom's unbeaten streak that was at stake. Instead, the legendary career of Michaels was also on the line in a special Streak vs. Career match.

    For the second year in a row, HBK and The Deadman captivated fans with a masterclass in storytelling. Michaels threw everything at his opponent, and when none of it worked, the beaten and defiant Michaels mocked his opponent's mannerisms. One Tombstone later and one of the most storied careers in professional wrestling was over for a second time.

    The extraordinary match, the show of respect afterward and the long walk up the ramp by Michaels as he wrote the latest chapter of his career (until the Saudi Arabia debacle) made for an unforgettable moment. The match itself would have been excellent in a vacuum, without the emotion surrounding it. 

8. WrestleMania XIV vs. Ric Flair

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    Imagine working with your idol; the person responsible for shaping you into the person and professional you are today. Few people ever have that opportunity, even fewer on the most significant stage in their field.

    That was the position Michaels was in at WrestleMania XXIV in 2008.

    The Heartbreak Kid had competed against Flair before, but with the added element of The Nature Boy's career being at stake on the WrestleMania stage, pressure was on to deliver a match befitting the enormity of the moment.

    He did.

    Flair put in the work, but it was a one-man show as Michaels strove to give his childhood hero the match he deserved in what would be his final outing as an in-ring performer in WWE. All while nursing cracked ribs suffered early on following a missed top-rope moonsault that saw him land on the edge of the commentary table.

    Shaking off the bumps, bruises and certain agony, Michaels rocked his mentor with Sweet Chin Music. When the defiant Flair stood, fists clenched and dared his opponent to put him down, Michaels obliged, but not before telling him he loved him and that he was sorry.

    The emotional storytelling of this match trumped any physicality. From an action standpoint, it was a very basic match. But the story that Michaels and Flair told on that night resonated with fans, leaving them teary-eyed at its conclusion.

    For a performer whose legacy is defined by his storytelling prowess, this ranks among Michaels' very best.

7. In Your House 2 vs. Jeff Jarrett

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    Among the most underrated matches of his career and an entire generation, the Intercontinental Championship match between Michaels and Jeff Jarrett at May 1995's In Your House 2 pay-per-view was a work of in-ring artistry.

    Smooth, crisp and borrowing from old-school Southern wrestling storytelling, it stole the show out from underneath higher-profile matches like Sid vs. Diesel and confirmed Michaels' greatness to anyone still in doubt.

    It also proved that Jarrett, himself riding a wave of strong performances that year, was more than a wannabe country singer. He was a veteran capable of performing to the level of any opponent, even when that is, arguably, the greatest to ever lace a pair of boots.

    Michaels won the match and the title, beginning an ascent toward the main event. The quality of the match only served to support management's desire to turn him into the next face of the company within the next year.

6. In Your House: Mind Games vs. Mankind

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    Credit: WWE.com

    Entering September 1996's In Your House: Mind Games, Michaels was the reigning WWE champion and top star in the company, but he lacked the edge fans wanted to see from their wrestlers. He was flamboyant, flashy and cocky, but he needed to be tougher.

    Mankind was tasked with dragging that out of Michaels and did so brilliantly in a five-star classic.

    Michaels found himself on the receiving end of a beating, an onslaught of punishment at the hands of the challenger. When he fought back, he did so with the aggression that he had been lacking, matching that of his opponent. He viciously targeted the knee of Mankind, attacked him while his head was trapped in between the top and second ropes and even drove him through an announce table by reversing a side suplex from the top rope.

    The grit and guts shown by Michaels were exactly what the Heartbreak Kid needed to win over fans who were not impressed by the glitz and glamour and his unmatched in-ring skill set.

    The match would end in a disappointing disqualification after The Undertaker and Vader got involved, but that does not diminish the extraordinary fight that preceded it.

    Considering ECW stars made their presence felt earlier in the night during less-than-fantastic television, the fact that the violence-loving Philadelphia fans found themselves so immersed in the action Michaels and Mankind provided is a testament to the physicality they delivered and the story they told.

    When discussing Michaels' best, this match is often inexplicably left out. An instant classic and a match that was mutually beneficial for both stars. 

5. WrestleMania 21 vs. Kurt Angle

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    Two of the best wrestlers in the world took to the biggest stage in professional wrestling in April 2005 when Michaels battled Kurt Angle one-on-one at WrestleMania 21.

    With expectations through the roof given the quality of the performers involved, there was an incredible amount of pressure on HBK and the 1996 Olympic gold medalist to deliver. They did, crafting an instant classic that still ranks among the best in WWE history.

    A match full of counters and reversals, telling the story of elite wrestlers at their pinnacles, it kept the fans in Los Angeles glued to the action like a summertime Hollywood blockbuster. In the end, it was Angle who trapped Michaels in the ankle lock, keeping his grasp tight for two minutes before an exhausted and defeated HBK tapped out.

    Again, Michaels shined in defeat. Angle may have gotten the win, but the former world champion added another extraordinary match to his WrestleMania resume.

4. In Your House: Badd Blood vs. The Undertaker

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    For the first time ever, WWE unleashed Hell in a Cell on its fans at In Your House: Badd Blood.

    Inside the imposing steel structure, Michaels and The Undertaker wrote the most violent, bloody chapter of their storied rivalry. 

    Left to face the wrath of a man he first infuriated two months earlier by costing him the WWE Championship, Michaels sold the ass-kicking like no other. His body battered and his face bloodied, he appeared destined to end up on the losing end of the historic first-time match.

    Enter, Kane.

    The Big Red Monster emerged from exile for the first time, struck his brother down and ensured the slimy, sneaky HBK would steal the win.

    Tasked with introducing the match type to the audience, Michaels again set the standard. He provided the blueprint that arguably has yet to be eclipsed by any pairing. The overall quality and the fact that it is still discussed as one of, if not the, greatest of its kind is a hallmark of many of HBK's greatest bouts.

3. SummerSlam 2002 vs. Triple H

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    Credit: WWE.com

    The idea of an athlete leaving their chosen profession following serious injury, taking eight years off, then returning better than they were before is absurd. It's not feasible. It's not something that makes any sense whatsoever.

    It doesn't compute.

    That is why Michaels' return from the back injury that sidelined him for four years is so incredible. Here was a guy at the height of his profession. He was, almost inarguably, the best wrestler on the planet. Then he was gone, forced to watch from the bench as the industry passed him by.

    At SummerSlam 2002, he returned to the ring amid a betrayal storyline with best friend Triple H and proceeded to have a Match of the Year candidate. A non-sanctioned street fight, it would allow him to mask any weaknesses or limitations with weaponry and high spots.

    He didn't need anything to be hidden, though. Michaels rediscovered the tenacious pitbull-like fighter he was prior to his departure from the company and proceeded to have a hell of a match with The Game. The two competitors wowed fans on Long Island, New York, and left them wanting more.

    Michaels would win the match via jackknife rollup, then proceed to give the fans exactly what they wanted, beginning three months later at Survivor Series and never looking back. 

    The classic SummerSlam battle was the start of a career rejuvenation that would last another eight years and span countless incredible in-ring performances.

2. WrestleMania X vs. Razor Ramon

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    The match that catapulted Michaels to stardom in WWE.

    Prior to the ladder match to crown the undisputed intercontinental champion, Michaels was a good hand with a ton of upside. After the match, he was the talk of the industry; an architect of one of the best and most influential matches in wrestling history.

    With Razor Ramon, HBK set the bar for the ladder match, meshing unmatched athleticism and punishing physicality to create an instant classic.

    As history (and this list) tells us, Michaels had a knack for stealing the show even in defeat, grabbing the attention of fans and critics alike and enhancing his legacy. In this instance, he also ignited the long and storied history of an iconic match type.

1. WrestleMania XXV vs. The Undertaker

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    The label "greatest match of all time" gets thrown around a lot, but never was it more apropos than in the moments following Michaels' epic encounter with The Undertaker at WrestleMania XXV. That contest was a dramatic masterpiece that had fans in Houston hanging on ever near-fall and false finish.

    Two icons of the industry with great familiarity, HBK and The Phenom countered and reversed nearly everything they threw at each other, culminating in a finish that saw The Deadman catch Michaels during a moonsault press attempt and drive him into the mat with a Tombstone piledriver for the pinfall victory.

    The victory extended The Undertaker's unbeaten streak on wrestling's grandest stage and finally provided him a legacy-defining match on the WrestleMania stage.

    For Michaels, it was further evidence of his excellence. He had long ago earned the nickname "Mr. WrestleMania," and most expected a fantastic match between him and his Hall of Fame-worthy opponent. They did not expect every spot to be flawless, the timing to be superb and the crowd to be as lava-hot as it was for the showdown.

    The match won nearly every Match of the Year award, and justifiably so. Renowned for the ride it took fans on, it remains one of the most acclaimed matches of the last 25 years and, in the grander scheme of things, has entered the conversation for best match of all time honors.

                

    The Definitive List... is an ongoing series detailing the 10 greatest matches in the careers of wrestling's greatest Superstars. Catch up now with these previous installments: "Macho Man" Randy Savage, The Attitude Era, Scott Hall, Mick Foley, Kurt Angle and Trish Stratus.

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