With SmackDown tonight celebrating 25 years of Triple H in WWE, we take a look back at the top five matches of his illustrious career.
On tonight’s episode of SmackDown on FOX, they’ll be celebrating the 25th anniversary of the WWE debut of Triple H. Originally appearing in taped vignettes in 1995, Hunter Hearst Helmsley made his in-ring debut on the April 30, 1995 episode of Wrestling Challenge.
Over the years, Hunter Hearst Helmsley was often shortened to HHH and eventually morphed into Triple H. Long before he was the Executive Vice President of Global Talent Strategy & Development for WWE, Triple H was one of the squared circle’s most calculated competitors, earning the nickname “The Cerebral Assassin” from Jim Ross.
Triple H has found himself embroiled in rivalries with seemingly every notable wrestling figure of the last two decades. The Rock, Steve Austin, Mick Foley, Shawn Michaels, Kurt Angle, Chris Jericho, Batista, John Cena, Daniel Bryan, and Roman Reigns are just a few of those names.
The skill and consistency The Game has shown led to the impressive longevity of his career, though being Vince McMahon’s son-in-law surely didn’t hurt. Though some fans will push back and argue Triple H’s best matches were often carried by his opponents, these five stood out among the pack and illustrate the toughness, skill, and in-ring storytelling that has led to his storied 25-year WWE career.
5. Elimination Chamber Match for the World Heavyweight Championship: Triple H (c) vs. Shawn Michaels vs. Chris Jericho vs. Kane vs. Booker T vs. Rob Van Dam [Survivor Series 2002 at Madison Square Garden in New York, NY]
The first entry in our list is the only one to contain more than two competitors in total. Triple H has appeared in six different Elimination Chamber Matches, scoring the win in four of those. While the match eventually began to evolve, few have been able to overcome the precedent set when we first saw the Elimination Chamber at Survivor Series 2002.
The match came a few short months after Shawn Michaels miraculously returned from a career-ending back injury, which is mind-boggling considering the level of danger in this kind of a match. The modern Elimination Chamber has been re-designed to facilitate spectacular moments while emphasizing superstar safety, but this first one didn’t have any of that.
This Elimination Chamber was nothing short of brutal, and Triple H was on the receiving end of much of that. During the match, Rob Van Dam attempted a Five Star Frog Splash off one of the pods while Triple H was too close. As a result, RVD landed with his knee and leg crushing the throat of Triple H.
The swelling on the trachea and esophagus of Triple H made it nearly impossible for him to breathe or talk, but that didn’t stop him from continuing all the way to the end of the match including an elongated final stretch against Shawn Michaels. This fantastic match had great work by all six men, and really highlights the mind-boggling toughness of Triple H.
4. Hell in a Cell Title vs. Career Match for the WWE Championship: Triple H (c) vs. Cactus Jack [No Way Out 2000 at Hartford Civic Center in Hartford, CT]
Back in September, I took the time to rank all 40 (at the time) Hell in a Cell Matches from worst to best. In order to do this, I went back and watched every single one to properly evaluate them. When the dust settled, one stood above the rest. The undeniable number one was an epic clash from No Way Out 2000.
Going back to that time, it looked like Mick Foley was winding down his career and wanted to go out in the most spectacular way possible. With that in mind, he made one last attempt to take the WWE Championship from Triple H and made the step of putting his career on the line in the process.
Foley once again brought his Cactus Jack persona to the fight, which he’d done only a month prior at the Royal Rumble. While Foley had already experienced Satan’s Structure, this was the first of Triple H’s nine appearances inside Hell in a Cell. Unsurprisingly, the chaos between these two eventually spilled outside of the cell and brought things up a notch.
There were plenty of powerfully violent moments in this contest, easily the most memorable was Triple H back body dropping Cactus Jack all the way through the top of the cell and through the ring below. Ultimately, it was Triple H who took the win, but that didn’t stop Mick Foley from returning several more times in the future.
3. Triple H vs. Daniel Bryan [WrestleMania 30 at Mercedes-Benz Superdome in New Orleans, LA]
Most of the matches on this list are violent bloodbaths. Throughout his lengthy career, Triple H always knew how to take things up a notch when weapons and structures could get involved. However, there is one pure wrestling match that stands far above the rest.
The third best match in his career, and by far the best regular singles match, saw Triple H take on Daniel Bryan in the opening match of WrestleMania 30. Going into the match, Triple H represented The Authority which fought so hard to keep down Bryan, who they believed to be only a “B-Plus Player.”
While some might see this entry and feel like Daniel Bryan, who is arguably one of the greatest in-ring performers and wrestling technicians of all time, carried Triple H to this highly rated contest. While Bryan’s role can’t be understated, Triple H deserves a lot of credit for the story he told here with some traditional limb-targeting on the already injured arm and shoulder of Daniel Bryan.
On top of that, Triple H actually pushes himself to pull out maneuvers that haven’t always been a staple of his in-ring arsenal, including a devastating Tiger Suplex targeting the damaged shoulder of Bryan.
Ultimately, it was Bryan who took the win, but Triple H kept moving the story forward with a post-match attack that made Bryan’s eventual title win at the end of the night that much more unbelievable.
2. Unsanctioned Street Fight: Triple H vs. Shawn Michaels [SummerSlam 2002 at Nassau Veterans Memorial Coliseum in Uniondale, NY]
When Shawn Michaels retired in 1998 with a career-ending back injury, fans all believed we’d never see him compete again. While he did appear as an on-screen character a few times in the following years, we didn’t see him back in a match until SummerSlam 2002. Similar to the previous entry, this match was elevated by the story going into it.
Not only was it Shawn Michaels’ miraculous in-ring return, but the match itself came from a violent turn by Triple H. The former best friend and D-Generation X member attacked Michaels during a brief reunion on Monday Night Raw. In the following weeks, someone attacked Michaels in the parking lot and drove him head-first through a car window.
Seemingly breaking away from his grudge, Triple H rushed to his friend’s side and expressed his anger over the attack, vowing to find out who had done it. Of course, we eventually found out the perpetrator was none other than Triple H. All of this culminated in an Unsanctioned Street Fight between Shawn Michaels and Triple H that showed both men push themselves further than most expected.
Holding nothing back, the violent fight showed fans what Michaels was capable of. The shockingly sudden victory by HBK led to an eardrum-shattering crowd reaction, and that shifted to furious boos when Triple H struck Michaels in the back with a sledgehammer following his loss.
1. Street Fight for the WWE Championship: Triple H (c) vs. Cactus Jack [Royal Rumble 2000 at Madison Square Garden in New York, NY]
Honestly, when I started ranking these matches I did wonder how things would end up. At least, I wondered how the other four would end up. I knew from the start which match would top the list, because it remains to this day the best match of Triple H’s career and one of my favorite matches of all time.
If you like violence, you’ll love this contest. In early 2000, The Game found himself up against a character that seemed like a mythical creature. When Mick Foley revealed he’d be coming to the Royal Rumble as Cactus Jack, Triple H completely lost his mind with anger and fear.
With that memorable reaction, he told WWE fans everything they needed to know about Cactus Jack. If Mankind or Mick Foley were already tough and hard to kill, Cactus Jack carried that toughness through his violent offense in a way WWE had never seen before.
From barbed wire to thumbtacks, this match had it all. On top of that, it’s another showing of just how amazingly tough Triple H is as a competitor. During the course of the match, Triple H was suplexed onto a wooden pallet at ringside.
A stray piece of wood on the pallet punctured Triple H’s leg, causing him to bleed profusely as the match continued. Never one to stop the action, he fought through the pain and the loss of blood to ultimately defeat Cactus Jack in his own violent environment and retain the WWE Championship.