The icon, the showstopper, the main event, and Mr. Wrestlemania, are all been nicknames associated with WWE Hall of Famer Shawn Michaels and for good reason. He’s won Pro Wrestling Illustrated’s “Match of the Year” 11 times and 9 of the contests were at Wrestlemania.
Too many amazing matches to count for the Heart Break Kid but here is a list compiled of what in my humble opinion are his best mtches of all time. Some are sure fire and others may leave you scratching your head but all in all this list is not to be ignored.
10. Shawn Michaels vs Brett Hart Iron Man Match Wrestlemania 12
It was his time. The first time Shawn Michaels won the WWE World Title after going into overtime in an hour long Iron Man match with long time rival Brett “The Hitman” Hart.
The boy-hood dream of Michaels came true starting with an iconic zip line entrance into the ring at the Arrow Head Pond in Anaheim, CA and ending with an emphatic Sweet Chin Music to the face of Hart. This bout is on many lists of “greatest of all time matches” but it’s also on lists of “most overrated matches of all time.”
In my mind it’s a great bout with multiple spots and incredible in-ring wrestling chemistry but in certain instances it came off as too long and drawn out so I can see both sides. It isn’t further up the list because the wow factor is somewhat in the middle however the beginning and end to the contest were a must see.
This match received critical acclaim at the time and is the 1996 PWI Match of the Year.
9. Shawn Michaels vs Ric Flair Retirement Match Wrestlemania 24
The showstopper vs the 16 time world champion at Wrestlemania in a match that could have been Flair’s last. In the end, it was.
Vince McMahon set up the bout after a string of losses by Flair, telling him that if he was to lose to Shawn at Wrestlemania then his career would be over. However Flair responded with “it would be an honor to retire to Michaels.”
Even though Flair’s in-ring prowess had withered drastically over the years, he was still able to put on a memorable performance but Michaels (as always) carried the match for the most part. Michaels walked away with the victory after putting away the “Stylin’ and Profilin’ Flair with an iconic super-kick where right before Shawn delivered he mouthed 3 words to Flair in the 2008 PWI Match of the Year.
“I Love You.”
8. Shawn Michaels vs Chris Jericho Wrestlemania 19
Old school vs New School in a match that saw Jericho who had idolized Shawn in every aspect from the beginning of his wrestling career and wanted to prove he could beat the show stopper at a Wrestlemania.
This match had a high number of spots from Jericho super-kicking Shawn Michaels to Shawn utilizing a lion-sault, the pair stole the show. Even going up against a stacked card that was full of amazing matches including; The Rock vs Stone Cold 3, Kurt Angle vs Brock Lesnar and HHH vs Booker T.
After becoming the first ever WWE Undisputed Champion, this match solidified how far Jericho had come in the industry and that he was prepared to take the company to new heights. Even though Michaels won this incredible contest in the end, most remember this bout for what happened after Shawn’s hand was raised.
Jericho and Shawn embraced after the dust was settled in what seemed to be a heartfelt and respectful moment. the moment faded fast when Y2J low-blowed Michaels in furthering himself as being the top heel in the company.
7. Shawn Michaels vs The Undertaker Retirement Match Wrestlemania 26
The re-match to what many consider the best match in the history of sports entertainment. Undertaker bested Shawn a year prior and Michaels utilized the latter part of the year begging for a rematch with the Dead man, costing Undertaker title opportunities along the way.
Taker named the condition that if he was to win the contest then Shawn would have to retire in a case in which Michaels reluctantly agreed. The lust to end the Undertaker’s heralded Wretlemania streak and avenge his last loss to the deadman overshadowed the possiblity of ending his own career.
The match was a spectacle and is the 2010 PWI Match of the Year but lacked the electricity of the first pairing. The obvious chemistry between the two was on display as always and the story telling throughout seemed to emulate that of Shawn’s career which brought chills at certain intervals.
In the end after Shawn kicked out of numerous tombstone piledrivers, Taker advised Shawn to quit but that was never HBK’s style. Michaels looked up into the eyes of the Deadman while on his knees and mocked The Undertaker by grazing his fist across his own throat.
The Undertaker delivered another finishing maneuver and ended the match and career of HBK.
6. Shawn Michaels vs HHH Street Fight Summerslam 2002
Shawn Michaels returned to action in 2002 and formed an alliance with the NWO but then they all disbanded and Shawn pleaded with HHH to return to the company. HHH complied and the pair came out to the old school DX music and even dawned D-Generation X attire.
The reunion was short lived after Triple-H turned on Shawn in the ring and performed a pedigree to Michaels. Thus beginning a feud that would last for years but beginning with an epic match at that year’s Summerslam pay-per-view.
The pair went back and forth in pools of their own blood, HHH exploited the former back injury of HBK but as always Shawn was resilient. A cross body through a table and a flying elbow off of a ladder were some amazing high points in the bout but a weak ending kept this affair from being higher on the list.
After an all out war Michaels snuck away with a cheap roll-up victory. However he did pay for it when he celebrated and HHH snuck back inside the ring and battered Shawn with his signature sledge hammer in selling him bashing HBK’s back and solidifying a rivalry that was far from over.
5. Shawn Michaels vs Chris Jericho Ladder Match 2008 No Mercy
The man that invented the Ladder match in Michaels vs the man that has competed in the most modern day Ladder matches in Y2J Chris Jericho. This match was a culmination of the two’s most recent rivalry which was heated and personal so much more then their affair in 2003.
This time the World Heavyweight Title line and the pair put on the performance of a lifetime. Many believe this bout upstaged the first ladder match between Razor Ramon and Michaels and rightfully so. The new innovations of ladder usage combined with the kayfabe hatred the two had for each other culminated to be an epic battle.
Possibly the only reason that this match wasn’t match of the year was because that title already went to HBK vs Ric Flair that year but on this list, this bout in my mind had more high spots and jaw dropping moments and none bigger than the photo finish.
Both men reached for the belt at the top of the ladder and each man was able to grab the gold and a tug of war of gigantic proportions ensued. Jericho would resort (as always) to a heel tactic and headbutted Shawn to drop the former champion and Chris secured the close victory over his idol.
4. Shawn Michaels vs Triple H vs Booker T vs Rob Van Dam vs Chris Jericho vs Kane Elimination Chamber Match Survivior Series 2002
The first ever Elimination Chamber match delivered. It was the brain child of Raw General Manager Eric Bischoff and remains one of the most brutal matches one could compete in to this day. Like Jim Ross once said, “You don’t win an Elimination Chamber match, you survive it.”
This contest saw more spots than a dalmatian. Chokeslams, Pedigrees, Spin-a-roonies, Lion Saults, Superkicks and even a 5 star frog splash. It set the tone for and was the measuring stick for any chamber match to follow.
First went RVD, then Chris Jericho hit his stride and by eliminating Kane and Booker T only to taste Sweet Chin Music from Michaels. Shawn then went into a brutal contest (as always) with his rival for the year of 2002, HHH.
In the end HBK overcame all odds and delivered one final sweet chin music to the dome of Hunter Hearst Helmsley and secured the Big Gold Belt for the first time in his illustrious career.
3. Shawn Michaels vs Razor Ramon Ladder Match Wrestlemania 10
Much like the first Elimination Chamber match, Michaels also comepeted in the first ever Ladder match where he matched wits with “The Bad Guy” Razor Ramon. Yet again Mr. Wrestlemania stole the show in the PWI Match of the Year in 1994.
The implementation of the Ladder brought a level of creativity that the wrestling fan had not seen before. A cross body from the top of the ladder lifted fans from their chairs at the Madison Square Garden arena. The battle was for the rightful owner of the intercontinental title.
Michaels utilized his body guard Diesel to allow him to gain the upper hand and even delivered a pile driver and a sweet chin music to Ramon but in the end the Bad Guy reigned supreme on this night. However both men blazed the trail for ladder matches in the future.
2. Shawn Michaels vs Kurt Angle Wrestlemania 21
Whoa how is this match number 2 on this list? This contest is quite possibly the most underrated Wrestlemania match, Kurt Angle match, Shawn Michaels match or just plain match in general.
Their rivalry began at the Royal Rumble of 2005 when Michaels eliminated Kurt and in turn Kurt returned to the ring to have Shawn eliminated. Then Angle proceeded to batter HBK on the entrance ramp and performed his signature ankle lock and the feud began that would end in the 2005 PWI match of the year.
The match at Mania was a classic. Reversal after reversal, Michaels’s many attempts at his super kick were thwarted by Angle’s attempts at his ankle lock. The match allowed Shawn to use his speed and ring awareness to sell being manhandled by the mat wrestling and ring generalship of Angle’s
In the end Angle reigned supreme and the Olympic Gold Medalist had conquered the Heartbreak Kid and possibly put on the best performance of his career.
1. Shawn Michaels vs The Undertaker Wrestlemania 25
The first task at taking on the heralded streak of The Undertaker’s wrestlemania wins came at the 25th anniversary and it did not disappoint. Shawn and Taker had a memorable contest at the 1997 Royal Rumble in a Casket match then at the Royal Rumble leading up to the 25th Mania.
Like most movies, the original out performed the sequel. Shawn’s aerial offense was on display seemingly more than ever, from moon saults to super kicks to defiant kick outs of everything the Undertaker had to throw at Michaels.
In an event that was considered to underwhelm. From a ho-hum main event that saw Triple-H take out his former evolution partner Randy Orton. Before a triple threat title match featuring Edge, Cena and Big Show where what seemed to be the only high spot was when Cena lifted his other 2 advisories on his shoulders.
Michaels and Taker not only stole the show. They stole the year of 2009 as it was the PWI Match of the Year as Shawn took that honor 7 years in a row. The end came after yet again a plethora of finishers.
Micahels went for his patented moon sault only to be caught in the hands of the Deadman as he delivered a torrential tombstone piledriver to HBK. Undertaker crossed his arms, stuck out his tongue and picked up the victory in the best match of Shawn Michaels career and maybe the best match of all time.