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Triple H’s 8 Best And 7 Worst WrestleMania Matches

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Triple H’s 8 Best And 7 Worst WrestleMania Matches

As the self-proclaimed King of Kings and heir apparent to the WWE Universe through his marriage to Stephanie McMahon, no WWE superstar has a higher profile than Triple H. The Game has cemented his status by competing at the second most WrestleManias of any performer, behind only The Undertaker and his legendary Streak. Impressive as that looks on the surface, wrestling fans who prefer quality over quantity may not be as quick to applaud HHH’s efforts, considering at least half of his 20 appearances at the Grandest Stage of Them All were complete and total bombs.

Despite the heights he’s reached as both a wrestler and an executive, Triple H has never been more than a middling performer in the ring, inclined towards long and drawn out catastrophes whenever his opponent doesn’t have the skills and/or pull to reign in his ego-driven style. The result has been some horrible marquee matches, sometimes in the main event of the biggest show of the year, with the entire wrestling community suffering because of it.

On the flipside, the good bouts Triple H had at Mania often saw him genuinely do what was best for business, losing to rising stars at the perfect moment to make their careers. And then, of course, there was his three-match series with The Undertaker, which transcended issues of mere ego and went on to represent what pro wrestling was all about. Whether you love him or hate him, Triple H has clearly made quite the impact at the Showcase of Immortals, so keep reading to learn about his 8 best and 7 worst WrestleMania matches.

15. BEST: WrestleMania XII – The Ultimate Warrior

How much enjoyment one gets out of Triple H’s WrestleMania debut is inversely proportionate to how much one enjoys his career in general. The biggest Triple H supporters out there probably don’t have much to gain from watching him get squashed by  the Ultimate Warrior in some 99 seconds. But those who don’t much care for him might even call it the most satisfying moment of his career. Truth be told, there really wasn’t much to the match, as HHH merely played canon fodder for the Warrior’s big return after four years away from the business. It’s practically mere coincidence that the match also featured Sable’s debut as she escorted HHH to the ring. The match itself was too short to feature anything worth celebrating. On the other hand, a guy who would spend the lion’s share of his career burying young talent in drawn out disasters got his ass handed to him in less than two minutes — a preemptive taste of his own medicine if there ever was one. Granted, it could also be argued that were it not for this match, maybe Triple H never would have become such a jerk when it came to how he was booked.

14. WORST: WrestleMania XIX – Booker T

Removed from any context and viewed simply as a mid-show World Heavyweight Championship match at a random Pay-Per-View, the battle between Triple H and Booker T at WrestleMania XIX wasn’t half bad. Under different circumstances, it could have even ended up on the other half of this list. But there was one huge problem with the match that left a horrible taste in fans’ mouths. Had the build solely focused on Booker T attempting to win his first major WWE championship, nothing about the bout would need to change for it to wind up on the other half of this list. Unfortunately, the build wasn’t about Booker becoming a champion, but rather how he used to be a criminal, and how racist old Triple H thought that was indicative of Booker’s culture. HHH also mocked Booker’s “nappy hair” and said Booker’s job was to “sing and dance” for people like him. Therefore, when Triple H defeated Booker with ease, it didn’t matter that the preceding match was decent. What mattered was that the horrible racist with all the power proved his backward views correct, at least for that night. It’s no surprise some people still don’t accept HHH all these years later.

13. BEST: WrestleMania XXI – Batista

While the botched ending to the 2005 Royal Rumble kicked things off on somewhat of a down note, WWE more than made up for it with the resulting build to WrestleMania 21. Initially, Batista was set to challenge JBL for his WWE Championship, until he discovered his allies in Evolution were conspiring against him, chief amongst them group leader Triple H. Thus, when it came time to make his WrestleMania match official, Batista swerved Triple H with a thumbs up that quickly became a thumbs down, setting the tone for the rare feud where HHH almost never had the advantage. As their first encounter, the WrestleMania 21 main event wasn’t quite as good as their rematches at Backlash and Vengeance, largely because it took them about 10 minutes before the match really kicked into high gear. Once it did, though, the pace remained strong enough to get the crowd heavily invested in Batista’s victory — creating a genuine WrestleMania moment in his coronation as champion.

12. WORST: WrestleMania 2000 – The Rock, Big Show, and Mick Foley

Being the first time the WWE Championship was defended at WrestleMania against multiple opponents, the Showcase of Immortals had never had so much star power in one main event. Of course, there are both pros and cons to this distinction, as the fact is most matches with more than two competitors tend to get jumbled, especially when there’s no gimmick forcing the pace to remain high. Pacing is an important word in describing why this match was such a dud, with Mick Foley desperately needing retirement and neither Triple H nor Big Show exactly known for their stamina. Worse than any of that is the fact none of the four wrestlers were the real draw of the match, that being the alleged appeal of “a McMahon in every corner,” each superstar managed by a member of WWE’s first family. Not even the most electrifying man in sports entertainment could overcome these odds to entertain his millions and millions of fans, which, by the way, was all any of them wanted to see. Cut out Foley, Big Show, and all the McMahon’s — and WWE could have had a classic on their hands. But fans had to wait until Backlash to get a show worth watching.

11. BEST: WrestleMania XIV – Owen Hart

Pretty much every part of Owen Hart’s career to take place after his brother Bret jumped ship to WCW and caused the Montreal Screwjob was a long downward spiral, but the Rocket never stopped delivering in the ring. Triple H’s feud against Owen was emblematic of both these facts, with Hart constantly losing to HHH and Chyna to increasingly diminished returns, yet it was also driving the action in the ring enough such that HHH was legitimized as a rising star in the process. In many respects, the encounter was the first part of an long-running effort to have Triple H replace the departing Shawn Michaels as the leader of D-Generation X, further accomplished when HBK lost the WWE Championship later that night and solidified 24 hours later on Raw. Standing toe to toe with a respected long-term star like Owen made Triple H look like more than a comedy lackey or pretentious blueblood, slowly turning him into the Cerebral Assassin persona he wore as a main eventer.

10. WORST: WrestleMania XV – Kane

Well, at least it doesn’t have anything to do with Katie Vick. Despite not being anywhere near the worst match Triple H and Kane would have against one another in their careers, the WrestleMania XV counter still wasn’t anywhere near one of their best. Katie Vick may have been absent, but Chyna was still there, and in fact, this was yet another instance when the focus of the match had nothing to do with Triple H’s opponent. The real storyline was between Triple H and Chyna, who had turned on him to join the Corporation in the build to the show. Skipping ahead to the ending, things got seriously confusing when Triple H lost the match by disqualification because of Chyna turning on Kane, invalidating everything that had happened beforehand. On the bright side, very little of value was lost, as the match itself was spectacularly slow-paced and featured little action of interest. Given that it had little purpose on its own and was merely building to an unrelated finish, the match was also too long, wasting everybody’s time without any payoff in mind.

9. BEST: WrestleMania XXVII – The Undertaker

Always looking to one up his buddy Shawn Michaels, the second of Triple H’s three WrestleMania matches against The Undertaker was in many respects a continuation of the Dead Man’s battles with HBK over the previous two years. It was evident from the beginning that Taker and Triple H were going to take a more minimalist approach to the build than the epic and emotional circumstances leading to the Undertaker-Michaels bouts, with the two simply heading to the ring on an episode of Raw and menacingly pointing towards the WrestleMania sign — actually an irritating trend that has since overtaken actual storytelling. Notwithstanding the trope’s eventual overuse, in this case, it completely worked as a statement that both Undertaker and Triple H had reached points in their careers where their names alone could sell a marquee match. Even better, when it came time for the two to actually put on a match, the results were appropriately over the top and bombastic enough to live up to that reputation. As heavily lauded as the match was, however, the middle of a three-part series rarely lives up to the other two and serves more as a stopgap than anything else, thus knocking this one down a few pegs in comparison to the competitors’ other classics.

8. WORST: WrestleMania 13 – Goldust

Forget about superlatives like best or worst; the WrestleMania encounter between Triple H and Goldust is probably more likely to get called the most forgettable match of both men’s career than it is to be graded on its quality. Nearing 20 years after the bout took place, both Triple H and Goldust are still working for WWE, and yet this early feud has almost entirely been written out of history. Once again, the problem is that the wrestlers weren’t the focus, the real point of this match being that Goldust’s wife Marlena couldn’t seem to get along with Triple H’s valet Chyna, for reasons that were never really explained. Basically, in the era when Vince McMahon decided women’s wrestling didn’t matter, men had to literally fight the battles of the few women in the company, and sometimes, he was even lazy about doing that well. On top of that insulting sign of the times, there was also the issue that both Triple H and Goldust were notoriously slow-paced workers, especially at that point in their careers. The result was a repetitive, limited match featuring Triple H mostly hitting Goldust with his knee for 15 full minutes.

7. BEST: WrestleMania XX – Chris Benoit and Shawn Michaels

Hindsight being 20/20, it’s hard to blame anyone who would rather forget about WrestleMania XX altogether due to the bad memories it brings up. At the time, however, it was a truly euphoric experience for most wrestling fans, and one of Triple H’s finest performances as a villain finally receiving his comeuppance. Try if you can and return to a time before Chris Benoit was known as one of the most violent criminals wrestling had ever seen, and remember the era when the Rabid Wolverine was a highly respected veteran whom diehard fans had been waiting to break through as a main event star since he made his WCW debut in the early ‘90s. However, due to Benoit’s general lack of charisma, it seemed like that would never happen, until his hard work inside the ring suddenly paid off, and he won the 2004 Royal Rumble. Initially, it looked like Shawn Michaels was going to meddle away Benoit’s chances at glory, but in the end, all HBK did was add much needed psychology and pacing to the match, allowing all three men involved to work together and create an unforgettable classic.

6. WORST: WrestleMania 31 – Sting

What the hell was this match? From the second it was announced, no part of Triple H and Sting wrestling at WrestleMania made the slightest bit of sense. The build was entirely based on Sting standing up to The Authority on behalf of good guys everywhere, and yet, the second they got in the ring at the Grandest Stage of Them All, WWE appeared to change their minds and decide it was really about Sting being sad WCW was out of business. Or something. To gain a measure of revenge on WWE putting the company out of business, the nWo — who, by the way, had the sole goal of putting WCW out of business, and thus were Sting’s arch-rivals — came out to his aide in the match, for absolutely no reason that could ever make sense to anybody who had watched a single episode of Nitro. Triple H’s buddies in D-Generation X also ran in, presumably because things weren’t stupid or confusing enough when only one of the two greatest factions of the ‘90s had their legacy destroyed in a meaningless match. Topping off the bizarre pointlessness, when it was over, it was over — and never to be mentioned again.

5. BEST: WrestleMania XVII – The Undertaker

Believe it or not, eight years before The Undertaker started his series with Shawn Michaels, and thus a full decade before his second series with Triple H began, the Streak was barely even an issue in booking his WrestleMania matches. His match with Triple H at what many consider the best Showcase of Immortals in history was very much so indicative of this fact as it was pieced together less than a month before the show and was based on the simple fact they had never wrestled on Pay-Per-View before. Coming at a time when both wrestlers were receiving harsh criticism for how slow and repetitive their marquee matches could be, Triple H and The Undertaker nonetheless delivered an incredible brawl around the Reliant Astrodome that left fans strongly invested in their efforts. Though some fans would probably argue that both of their future WrestleMania encounters would surpass the first one, the fact that this came out of nowhere before the Streak was important effectively lowered expectations — meaning, the athletes could blow fans away when these two legends unexpectedly delivered something special.

4. WORST: WrestleMania XXV – Randy Orton

Even Triple H himself has admitted that things didn’t go as planned when he and Randy Orton headlined WrestleMania XXV. Granted, he blamed their failure on Shawn Michaels and The Undertaker having a much better match earlier on the show, leaving the crowd too tired to properly cheer for him against Orton. But the fact remained that an egotistical maniac was forced to accept that his ego had gotten the better of him. For reasons most people will never understand, Triple H decided he wanted his war against Randy Orton to take the slowest pace of all of his remarkably slow-paced affairs, despite an intensely personal build that saw Orton beat up Stephanie McMahon and her entire family. Rather than get intense and craft one of his hardened brawls, Triple H wanted the match to closer resemble a boring crawl, where next to nothing happened for an entire 25 minutes. Naturally, in recognition of this failure, Triple H kept feuding with Orton for another several months, although never quite working out the classic that could have justified the whole mess.

3. BEST: WrestleMania XXX – Daniel Bryan

Yes! Yes! Yes! For better or worse, and probably for worse, some three years removed from the event, WrestleMania XXX might have been the last time WWE actually listened to its audience and gave the fans what they wanted. That said, if it really was the end of Vince McMahon caring about his audience, at least the company went out on a high note. Even better, Triple H was willing to put his ego aside entirely for the greater good, cementing once and for all that Daniel Bryan was not some B+ player forever relegated to the midcard, but rather, an A+ main event superstar. Unfortunately, despite everything positive to be said about this match and WrestleMania XXX in general, the elephant in the living room was that things quickly went south for Bryan in the months following the show, albeit through no fault of his own, nor any other wrestler involved. Sad as that is, it doesn’t change how incredible the work Bryan did was up until his early retirement, up to and including this opening match classic against the boss that never believed in him.

2. WORST: WrestleMania 32 – Roman Reigns

No! No! No! Where does one even begin with this disaster? Every single element of the Triple H-Roman Reigns feud, which started brewing well before WrestleMania 32, disregarded the most basic tenets of storytelling and professional wrestling in favor of realizing the bizarre and baffling whims of Vince McMahon. Because of his high profile in the feud and the company, it would be reasonable to place some of the blame on Triple H, as well, since he could’ve easily said no to the idea of treating the most hated wrestler in the WWE Universe as some sort of implausible babyface hero. Worse than that, Triple H was definitely complicit in the outrageously boring pace of the match, as evidenced by how many times derogatory phrases like that have been used throughout this list. This marquee encounter was no different aside from the fans loudly voicing their displeasure the entire bout, chanting for literally anyone other than the wrestlers in the match. It would have been one thing if this was the final straw with Reigns and WWE realized it was over with him, but going full steam ahead to the indefinite future makes it certain that this was Triple H’s worst outing at WrestleMania… until or unless Vince makes him wrestle Reigns again.

1. BEST: WrestleMania XXVIII – The Undertaker

Whether or not it was really the end of an era, Triple H, The Undertaker, and Shawn Michaels definitely created something special when they stepped inside the Hell in a Cell at Hard Rock Stadium. Unlike when The Undertaker stepped into the 16 feet of steel at the Grandest Stage of Them All against Shane McMahon or The Big Bossman, this time around, it actually felt deserved. Also different from the norm was that Triple H more than delivered his end of the match, shedding all his tendencies towards stalling and dragging things to a halt in favor of a vicious, hard fought battle with constant surprises and false finishes. Truth be told, not even Hell in a Cell was enough to elevate Triple H to Shawn Michaels’s level, as both HBK-Undertaker matches blow this one out of the water, definitively proving Triple H is, at best, the third greatest WrestleMania performer regardless of him having the second most matches. Of course, numbers one and two were involved in this match as well. And with that amount of star power working together for a concerted goal — end of an era or not — the match defined what the term Showcase of Immortals was all about.

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