Still Playing the Game: Triple H’s Top 10 WWE Moments

If it hadn’t been for this infamous night in Madison Square Garden on May 19, 1996, Triple H may have never evolved into the superstar that he is today. For a time, The Game was “persona non grata” with WWE, and it was all because of “The Curtain Call.” 

In an unscripted moment, Triple H and Shawn Michaels embraced their offscreen buddies (and onscreen rivals), Scott Hall and Kevin Nash, in a farewell gesture in the ring before Hall and Nash left for WCW. At the time, breaking character in such a way was completely taboo in the industry, especially when it revealed that the “good guys” and “bad guys” were actually friends in real life.

With Nash and Hall leaving the company that night, Vince McMahon had to discipline someone for the event. Since Shawn Michaels was the WWE champion at the time, not much action could be taken against him, and so as a result, Triple H (then known as Hunter Hearst Helmsley) found himself on a massive losing streak until management felt he had served his punishment. These days, with WWE having won the war against WCW, the Curtain Call is remembered more fondly, and has been recreated numerous times by fans and WWE superstars alike.

If the Curtain Call had set the stage for pushing WWE’s creative boundaries, then it’s fair to say that D-Generation X blew the curtain up in 1997. The original DX was comprised of Triple H, Shawn Michaels, Rick Rude, and Chyna, and they personified WWE’s “Attitude Era” where rules of taste and decency were driven to the edge. 

D-Generation X played an important role in the Monday night TV ratings war with WCW, and their entertaining skits and crude humor gained WWE millions of new fans. DX also had one of the coolest entrance themes in wrestling history. Since the group’s first hoorah, there have been many additional team members, with Triple H serving as the most active of all. 

Triple H played the game and became WWE’s official King of the Ring in 1997, but his true crowning moment came as part of a stunning WrestleMania 30 entrance. Introduced by wife, Stephanie, the Cerebral Assassin sat on an elaborate throne wearing a skull-crown and flanked by three unknown masked beauties who would go on to find their own WWE fame (Charlotte Flair, Sasha Banks, and Alexa Bliss).

This iconic ring entrance became a moment that encapsulates Triple H’s unique position as both an active main event competitor, as well as being mentor to WWE’s future superstars. Long live the king. 

Revered for his spectacular WrestleMania entrances, The Game raised the stakes further at WrestleMania 31 to become a vision of the Terminator. Wearing a suit of titanium that looked to have been grabbed straight from the shelves of Skynet, The Game was raised up to the stage on a platform as he held aloft the decapitated cyborg heads of enemies past. 

As the King of Kings readied himself to enter the ring against Sting, fans in California went wild when the Australian Oak, Arnold Schwarzenegger himself, appeared on the big screen dressed in full Terminator regalia. Arnie kicked off the action by asking the thousands in attendance: “Are you ready to play the game?”

By 2016, Triple H had almost completely swapped his trunks for a suit and tie, but after winning the Royal Rumble, he found himself defending the belt against a younger, hungrier lion in the form of Roman Reigns. 

While Trips ultimately lost the match and the WWE Championship that night, he proved to a record-breaking AT&T Stadium audience of more than 100,000 in Dallas that he could still deliver a top-notch main event. In the months leading up to the WrestleMania 32 bout, The Game stepped up his training and kept Instagram followers enthralled with his progress. He even appeared on the cover of the March 2016 issue of Muscle & Fitness, proving that our man will still be game for years to come. 

The rivalry between Triple H and the many faces of Mick Foley is perhaps the most intense feud in WWE history. These warriors battled it out under all kinds of match stipulations, including Falls Count Anywhere and No Holds Barred, but their Hell in a Cell match at No Way Out 2000 was the most brutal of all. 

Weapons, such as steel chairs and barbed wire, were allowed into the ring and the battle eventually spilled over to the top of the cell structure. As Cactus attempted a piledriver, The Game reversed the move sending his opponent through the roof of the cell and down onto the mat below. This allowed Triple H to score the pin, (temporarily) retiring Cactus Jack in the process. 

Trained by the legendary Killer Kowalski, Paul Levesque made his pro wrestling debut in 1992. Since that time, The Game has won the WWE Championship on nine occasions. He’s also been WWE’s World Heavyweight Champion five times, making him a 14-time world champion in total. Only John Cena and Ric Flair have won more. 

Triple H earned his first WWE Championship in 1999, defeating Mankind in a wild match on the August 23 episode of Monday Night RAW. 

Longtime pro wrestling fans will remember that 1998 was a year of hot TV ratings competition between WWE Monday Night RAW and WCW Monday Nitro. With both promotions desperate to outdo the other, The Game captained a real-life invasion of WCW’s flagship show. 

At the helm of a Jeep, complete with rocket launcher, Triple H and his DX teammates donned soldier attire and headed straight to the arena where WCW was filming its show. Segments of the invasion were shown throughout RAW as Triple H and his DX army attempted to gain entry to WCW’s broadcast. While they never quite made it into the arena, the clips of WWE superstars putting WCW under siege remains some of the most entertaining footage you’ll see. 

In one of the biggest swerves in WWE history, The Game revealed to a live television audience that he’d married the boss’s daughter, Stephanie McMahon, in Las Vegas. The twist? Steph had been passed out the whole time and didn’t even know the drive-thru nuptials had happened until The Game’s big reveal on Monday Night RAW in 1999.

With Stephanie scheduled to marry her fiancé Test, Triple H dropped the bombshell by showing video footage from that fateful night in Sin City. The incident sent shockwaves throughout the WWE and was just the first chapter in a story that has lasted 20 years. Today, Triple H and Stephanie McMahon are a true power couple and are married in real life.

When Triple H took on the Undertaker in a Hell in a Cell with special guest referee Shawn Michaels at WrestleMania 28, we were treated to one of WWE’s most memorable encounters and perhaps Triple H’s greatest showing. Following the match, which Undertaker won, there wasn’t a dry eye in the house as the warriors embraced in a true showing of sportsmanship and respect. Even in a loss, the Cerebral Assassin became immortal to fans who appreciated his efforts. At the time, we thought it was the final chapter in the war between Triple H and the Undertaker… but it’s not game over just yet.

Incredibly, more than six years after their last encounter, Triple H will face the Undertaker one last time on October 6 in Melbourne, Australia, as part of WWE Super Show-Down.