One doesn’t earn the nickname “The Showstopper” for nothing. True to that accurate moniker, wrestling legend Shawn Michaels has made a career out of headlining events throughout his 26-year-long career.
Debuting in 1984, Michaels became known as one-half of the Golden Age tag team, The Rockers, up until 1992. From there, The Heartbreak Kid broke out on his own, establishing himself as a brash, cocky heel whose self-inflated ego and high-flying skillset left fans in awe. Becoming the breakout star of WWE’s New Generation, Michaels went on to play a key role in the company’s influential Attitude Era, before serious injuries left him sidelined for four long years.
Returning in 2002, Michaels went on to enjoy an engrossing comeback in WWE, feuding against the future stars of tomorrow, as well as encountering more than a few familiar faces from his past. Looking back, Michaels' iconic career establishes him as one of the best professional wrestlers to lace up his boots, feuding against Hulk Hogan, Steve Austin, Bret Hart, Triple H, and John Cena, among many others.
From his career-making matches against Razor Ramon to his final feud against The Undertaker, Shawn Michaels's greatest wrestling matches ranked from best to worst.
Shawn Michaels vs. The Undertaker (WrestleMania 25)
In the grand scheme, no two wrestlers have a stronger association with WrestleMania than Shawn Michaels and The Undertaker. Reigniting their fierce rivalry from the early Attitude Era, Mr. WrestleMania challenged The Undertaker at the grandest stage of them all in 2009, hoping to become the first man to break the Dead Man’s legendary undefeated streak.
An incredible match that had drama, theatrics, technical wrestling, and plenty of climactic near-falls, Michaels and The Undertaker’s first WrestleMania encounter is without a doubt the finest match ever featured at WrestleMania – perhaps even the best in wrestling history. Making use of their expert chemistry, distinct move-sets, and iconic reputation, The Undertaker and Michaels stole the show at WrestleMania 25, leaving fans speechless with their constant reversals, hard-hitting blows, and out-of-nowhere finishers.
Shawn Michaels vs. Kurt Angle (WrestleMania 21)
What do you get when you mix the Olympic Gold Medalist, Kurt Angle, and The Showstopper, Shawn Michaels? One of the greatest wrestling matches of all time. Crossing paths for the first time at the 2005 Royal Rumble, an embittered Angle challenged The Heartbreak Kid to a match at WrestleMania 21, paving the way to one of the notable matches in either man’s career.
Like Michaels’ clashes with Bret Hart in the late ‘90s, the bout between HBK and Angle revolved more around mat-based technical wrestling than over-the-top punches and kicks. Alternating between submission holds, suplexes, and an occasional high-flying move (courtesy of Michaels), Michaels’ unique chemistry with Angle helped their first match achieve the same acclaim as HBK and The Hit Man's rivalry years earlier, laying the groundwork for several other momentous matches between the Wrestling Machine and Mr. WrestleMania.
Shawn Michaels vs. Triple H vs. Chris Benoit (WrestleMania 20)
An unsung WrestleMania classic forever overshadowed by Chris Benoit’s personal actions, it’s impossible to take anything away from the main event of WrestleMania 20, just as it’s impossible to diminish the esteem this match holds for fans across multiple generations of WWE viewers. Winning the 2004 Royal Rumble, the Rabid Wolverine decided to challenge World Heavyweight Champion Triple H at WrestleMania 20, with a vindictive Shawn Michaels inserting himself in their feud in the hopes of defeating his former best friend at the grandest stage of them all.
Intense, violent, and loaded with drama, the main event of WrestleMania 20 made for one of the most exciting matches in WrestleMania history. The three men maintained a fantastic dynamic together, Benoit making for a fascinating counterweight to Triple H and Michaels’ ongoing feud. With the audience firmly in Benoit’s corner, the Canadian Crippler managed to do the unthinkable, beating two of the company’s biggest stars. Rejoicing with his best friend Eddie Guerrero, the victory celebration had the Madison Square Garden fans cheering themselves hoarse.
Shawn Michaels vs. The Undertaker (WrestleMania XXVI)
Having pushed Undertaker to his limits at WrestleMania 25, an obsessive Shawn Michaels spent the next year thinking about how close he came to breaking ‘Taker’s Streak. As 2010 approached, challenging The Undertaker to a rematch seemed to be the only thing of interest to Michaels. Agreeing to a high-stakes a Streak versus Career match, The Showstopper laid it all on the line in his quest to bury the Dead Man, ending their decade-long rivalry at WrestleMania XXVI.
While Michaels’ match against The Undertaker at WrestleMania 25 might have been the more physical and unpredictable of the two, their WrestleMania XXVI rematch is far from a horrible match. In point of fact, between its cinematic near-falls, high-risk maneuvers, and climactic finish, it proved to be a bout as emotional as Michaels’ own retirement match against Ric Flair two years prior.
Shawn Michaels vs. Razor Ramon (WrestleMania X)
There’s a common misconception that Shawn Michaels versus Razor Ramon at WrestleMania X marked the first Ladder match in wrestling history. (The first Ladder match had actually been Shawn Michaels versus Bret Hart about two years before HBK and Ramon’s clash in 1994.) With how entertaining the final bout between Ramon and Michaels at WrestleMania X had been, though, it’s fair to say it’s one of the most influential matches in WWE.
An ingenious and innovative bout, Razor Ramon versus Shawn Michaels had all the air of unpredictability of a classic Attitude Era match, the two men performing unique ladder-based moves the likes of which no one had ever seen before. Taking some nasty-looking spills, hopping off the top of the token ladder, and using the household appliance as an effective weapon, Ramon and Michaels set the standard for the Ladder match for years to come.
Shawn Michaels vs. Bret Hart (WrestleMania XII)
It’s difficult to choose Shawn Michaels’ absolute best opponent, but that honor might just go to Bret Hart. A recurring thorn in each other’s sides both behind the scenes and in the ring, Michaels and Hart’s rivalry is the stuff of legend within WWE, culminating in several fantastic matches from their earlier ‘90s bouts to their eventual encounter at WrestleMania XII.
Over the course of an hour, Michaels and Hart engaged in a grueling Iron Man match, testing the endurance, stamina, and resilience of both men. Relying on mat-based wrestling for a majority of the bout, the match itself may divide most fans – some viewing it as slow-paced and tedious, others seeing it as a sound technical wrestling match that demonstrated the unique chemistry Michaels and Hart possessed. Regardless of individual criticisms, the match’s ending – which saw Michaels win his first WWE Championship – gave fans one of the most important moments in HBK’s career.
Shawn Michaels vs. The Undertaker (Badd Blood: In Your House)
After costing Undertaker a title victory over Bret Hart at SummerSlam 1997, HBK and the Phenom became embroiled in an intense feud for the remainder of the year. After their inconclusive match at Ground Zero: In Your House, the Dead Man challenged Michaels to ta match at Badd Blood: In Your House, negating any possibility of Michaels’ D-Generation X stable interfering.
In the resulting match, The Undertaker and Michaels demonstrated the unpredictable nature of the match as well as how violent an in-ring environment the Cell could be. Brawling in the ring and along the floor, the two eventually managed to bust their way outside the Cell, battling in front of and, before very long, on top of the Cell itself. With Michaels left a battered and broken mess by the time ‘Taker was preparing to deliver his Tombstone, only the timely arrival of Kane (in his debut appearance) saved HBK from the Dead Man’s clutches.
Shawn Michaels vs. Triple H (SummerSlam 2002)
Returning as an active performer in mid-2002, Shawn Michaels soon reunited with his former D-Generation X tag teammate, Triple H. After Triple H showed his true colors – blindsiding his former best friend and attacking Michaels in a backstage parking lot – their feud led to a match at SummerSlam 2002, Michaels’ first wrestling outing in over four years.
Bearing little sign of ring rust, Michaels seemed not to have aged a day in his temporary four-year retirement, battling Triple H with the ease of his earlier pre-injury self. Bashing each other with trash cans, steel chairs, and Michaels’ leather belt, the former DX stable mates had a stellar Street Fight, marking Michaels’ successful return to WWE, as well as the first in a long line of equally tremendous matches between HBK and the Game.
Shawn Michaels vs. Ric Flair (WrestleMania XXIV)
In 2008, the legendary Ric Flair’s career seemed to be winding down, the Nature Boy facing off against a variety of talents from late 2007 into the new year, each of whom attempted to beat Flair and force him into retirement. Triumphing over the likes of Randy Orton, Umaga, and Vince McMahon, Flair faced his ultimate challenger in the form of Shawn Michaels.
Squaring off at WrestleMania XXIV, Michaels, and the 59-year-old Flair had a match befitting the Nature Boy’s earlier encounters with Ricky Steamboat or Sting in the years prior. Though slowed by age, Michaels managed to make Naitch look like an absolute star in this match, ending Flair’s historic WWE career with an emotional Sweet Chin Music for the win.
Shawn Michaels vs. John Cena (Raw)
WrestleMania rematches are a given when it comes to WWE programming, whether said match comes months later on Raw or at the next pay-per-view following WrestleMania. More often than not, these rematches are decent events in themselves, but typically fail to live up to the earlier WrestleMania matches they're following up on.
Shawn Michaels versus John Cena on Raw is not one of these matches. Exceeding their earlier WrestleMania 23 match-up, Michaels and Cena conducted a whopping 40-minute long television match. Opting for a slower-paced opening filled with back-and-forth chain wrestling, the two then proceeded to introduce far more unpredictable spots (creative counters, stiff-looking slams, etc.). Like all-too-few matches, each move Michaels or Cena performed looked devastating, be it a Sweet Chin Music or a realistic-looking DDT. In the end, Michaels finally managed to pull one over on his former WrestleMania foe, countering the F.U. with an impressive back flip-superkick combination.
Shawn Michaels vs. Razor Ramon (SummerSlam 1995)
Just over a year after their iconic Ladder match at WrestleMania X, Shawn Michaels and Razor Ramon found themselves squaring off once again, this time at SummerSlam 1995. Despite not having any on-screen storyline build-up prior to their encounter here, Michaels and Ramon managed to catch lightning in a bottle once again, competing in an otherwise fantastic Ladder match that lived up to the hype of their earlier WrestleMania X showdown.
With both men booked as mutual babyfaces, Michaels did his best to fend off his former adversary, who took to targeting Michaels’ left leg throughout most of the match. Recreating and then subverting many of their WrestleMania X spots (such as Ramon dodging Michaels’ splash from the top of the ladder), Michaels’ victory over Ramon solidified his reputation as an increasingly popular babyface.
Shawn Michaels vs. Chris Jericho (No Mercy 2008)
Though an entertaining feud in the early Ruthless Aggression Era, Shawn Michaels and Chris Jericho’s rivalry reached its zenith in mid-2008, thanks in large part to Jericho’s character shift into the suit-wearing, straight-faced “Best in the World at What He Does.” For the next several months, the two clashed in an increasingly personal feud, leading to a Ladder match for Jericho’s World Heavyweight Championship at No Mercy 2008.
Following in the footsteps of their brutal encounter at Unforgiven, the subsequent Ladder match between Y2J and HBK made for an exciting affair, each wrestler making expert use of the ladders in their bout. Boiling down to an entertaining conclusion which saw both men partaking in tug-of-war for the title, only a well-delivered headbutt from Jericho helped the champ retain his title. It might not have been the final chapter in Jericho and Michaels’ 2008 feud, but it’s without a doubt the high point of their renowned rivalry.
Shawn Michaels vs. Mankind (In Your House: Mind Games)
It speaks volumes that Mick Foley considers one of his best matches to be against Shawn Michaels at In Your House: Mind Games. Earning a number one contender’s match for the WWF Championship, Foley’s mask-wearing, boiler room-dwelling alter ego, Mankind, challenged Michaels in the main event of Mind Games, marking the first match between these two wildly different ‘90s wrestlers.
Relying less on the street fighting style that made Foley an underground legend in ECW, Mankind’s match against Michaels stuck to fairly conventional standards, albeit with a few added twists. Favoring a more athletic move-set that consisted of suplexes, submission holds, high-diving attacks, and more than a few genuine-looking punches and kicks, the two had a terrific match-up here – one ruined by a disappointing finish involving interference from Vader and The Undertaker.
Shawn Michaels vs. Bret Hart (Survivor Series 1992)
While their later match at Survivor Series 1997 (complete with the infamous Montreal Screwjob) tends to receive the most attention from fans, Bret Hart and Shawn Michaels’ earlier encounter at Survivor Series 1992 is a thing of beauty in and of itself. Competing for Hart’s WWF Championship, the New Generation performer proved why they were destined to be WWE's future stars.
Like their later rematches, Michaels and Hart’s Survivor Series clash made use of extensive mat-based wrestling at the start of the bout, with Michaels more than able to hold his own against the Excellence of Execution. As the match went on, the two men desperately began to use every move in their repertoire, from flying offensive dives to hard-hitting backbreakers and suplexes. Though Michaels met with defeat, viewing this match today feels like watching a VHS tape of Michael Jordan playing college basketball in his youth, knowing the bright future each man would have in the years ahead.
Shawn Michaels vs. Jeff Jarrett (In Your House 2: The Lumberjacks)
One month after an unsuccessful attempt to win the WWF Championship from Diesel at WrestleMania XI, Shawn Michaels returned to WWE as a fan-favorite face, challenging Jeff Jarrett for the Intercontinental Championship at In Your House 2: The Lumberjacks. Perhaps the most underrated match in either man’s career, Michaels’ match and subsequent victory over Jarrett propelled him into becoming one of the most popular stars in WWE at the time.
Dodging the constant interference of Jarrett’s manager, The Roadie (later known as Road Dogg), Michaels proceeded to outsmart and outplay Double J throughout the bout, relying on his flexibility, agility, and high-flying moves to reclaim the title for the third time in his career.
Richard Chachowski is a freelance writer based in New Jersey. He loves reading, his dog Tootsie, and pretty much every movie to ever exist (especially Star Wars).