The WWE recently celebrated the 25th anniversary of Triple H’s debut. Love him or hate him, no one can deny that The Game was born for ‘This Business,’ to the point that he’s literally married to it. The Cerebral Assassin has come a long way from humble beginnings from the man formerly known as Terra Ryzing and Jean-Paul Levesque in WCW to the blue blood Hunter Hearst Helmsley and the whipping boy of the Kliq. Now he’s laid the foundation for the present and future of the company as the founder of NXT.
No one could have predicted that the man who got squashed by The Ultimate Warrior in his WrestleMania debut would evolve and thrive throughout the highly competitive Attitude and Ruthless Aggression Eras. The Game has had plenty of classic matches over the past quarter-century, but there are a few which ascended him into legendary status. Here are five iconic Triple H matches that made a huge difference in his ascent to the top.
Before he was the intimidating Heel with short trunks and scruffy facial hair, Triple H was the new leader of D-Generation X following Shawn Michaels’s back injury. Their feud with the Nation of Domination during the Summer of 1998 led to a ladder match between him and The Rock at SummerSlam for the Intercontinental Championship.
Four years after Shawn Michaels and Razor Ramon’s groundbreaking match at WrestleMania X, The Rock and Helmsley took the ladder match to the next level in this grueling battle that stole the show at SummerSlam. Both the Nation and DX interfered, including Triple H getting flour in his face, but a low-blow on The Rock by Chyna was enough for Helmsley to grab the title. Two years later, Triple H and The Rock’s rivalry rekindled over the WWF Championship, but the two never had a match as good as this classic.
By the dawn of 2000, Triple H was already positioned as the Heel champion of the then-WWF but hadn’t yet proved to the critics that he was worthy of the position. And then came the Royal Rumble. After weeks of bullying the lovable Mankind as the leader of the McMahon-Helmsley faction, Mick Foley morphed into the dangerous Cactus Jack right in front of his eyes.
The two collided over the WWF Championship in a street fight that showed what The Game was truly made of. A barbwire stick, thumbtacks, and a jagged shard of wood stabbing through Triple H’s calf were some of the highlights of this brutally violent battle at Madison Square Garden. Like most of Foley’s hardcore matches, he wound up losing to Triple H thanks to a pedigree on thumbtacks. This match and feud with Foley made Triple H worthy as the top Heel in the company, and he never looked back.
How do you top their brutal street fight at the Royal Rumble? Put Helmsley and Cactus Jack inside the Hell in a Cell, the same Cell that cemented Foley’s legacy as the Hardcore Legend in 1998 with The Undertaker. This match at No Way Out 2000 is surprisingly the only other Pay-Per-View Hell in a Cell match of Foley’s career, meaning Triple H got a huge honor of being his opponent.
Helmsley and Jack continued their intense brawling inside the cell, but once they broke outside was when things got crazy. Cactus had a barbwire stick set on fire and was about to piledrive Triple H on it on top of the cell, but The Game countered the maneuver and sent him falling through the cell reminiscent of 1998. Thankfully the ring was gimmicked for Foley to take the bump safely, and Triple H climbed down and hit the pedigree on Cactus Jack for the victory.
The first-ever Three Stages of Hell match took place between Stone Cold Steve Austin and Triple H at No Way Out 2001. This was the culmination of Austin and Helmsley’s intense feud, wherein kayfabe, it was Triple H who orchestrated Stone Cold getting run over by a car in 1999 and being out of action for nearly a year.
Austin won the first match under normal wrestling stipulations, Triple H won the second match that was a street fight, and they fought the final match inside a steel cage. In a clever finish, both Austin and The Game hit each other in the head with a weapon, but Helmsley landed on the Texas Rattlesnake and took the victory. Their epic contest lasted just under forty minutes, and the two best brawlers in the company kept it entertaining for every single minute of it.
By 2002 Triple H gained the reputation as someone willing to hurt anyone who got in his way, whether a friend or foe, but certainly Shawn Michaels had to be the exception. But in the Summer of 2002, the two former friends embarked on one of the most personal and intense feuds in WWE history. Triple H had returned earlier that year from a quad-tear as a babyface, but when he turned on Michaels’s for refusing to be his manager, The Game instantly became WWE’s top Heel again.
Anyone nervous about HBK’s back when the match started was quickly relieved in his first match in over four years. Michaels’s performed like he never left and put on one helluva show with Triple H, flying off ladders and putting his former best friend through a table. The match ended with Shawn getting the win with a sunset flip, but Triple H’s petty post-match attack to kayfabe injure his back again instantly gave him a ton of heat. The freshly clean-shaven Helmsley with blood on his face laughed manically while Jim Ross verbally crucified him on commentary.
The WWE will be celebrating the 25th anniversary of Triple H's debut on Smackdown, here are five matches that helped The Game become a legend.