Triple H and The Undertaker. The only two wrestlers who have been with the WWE since their respective debuts in 1996 and 1990 without taking any prolonged sabbatical or leaving for WCW. The two Attitude Era stalwarts first braved the gimmick–filled New Generation and led the Raw and SmackDown rosters during the first Brand Split. Each man’s career and legacy belongs in any Hall of Fame, from the WWE to Cauliflower Alley.
When two badasses like The Game and The Phenom have been in the WWE a combined 46 years, their paths are bound to cross on more than one occasion in a unique variety of ways. Whether it was an early but brief encounter on opposing teams at the 1995 Survivor Series or their later WrestleMania classics, both Icons would do all they could to make their moments memorable.
Between them, The Deadman and The Cerebral Assassin have a combined 41 championships, three Royal Rumble victories, and a whole heap of respect from fans and peers alike. Here are the top ten memories from their storied rivalry.
10 The Power Trip vs. The Brothers of Destruction – 2001 Backlash
Seldom did Triple H and The Deadman get it on with any partners. But at Backlash in 2001, the stakes were too high to limit their war to just the two future Hall of Famers. Then Intercontinental Champion, Triple H would team up with the WWE Champion, Stone Cold Steve Austin to take on the Tag Team Champions, Kane and The Undertaker, The Brothers of Destruction. For the first time ever, every single title in the company was on the line at the same time in one match! The four Superstars did battle in a grueling match, which saw interference from both Stephanie and Vince McMahon, who tossed Triple H the sledgehammer who nailed Kane for the victory, winning the belts for his team and becoming the second ever Grand Slam Champion in the process.
9 The Game Faces Judgment – Judgment Day 2000
Another of one of Triple H’s greatest rivals was The Rock. And even though The Rock had already gotten his title shot at WrestleMania, he would earn another shot, this time in an Iron Man Match at May’s Judgment Day. After dismantling each other for nearly an hour, The Game and The Rock were tied at five falls a piece. The Deadman, who had been on sabbatical for several months was set to return as evidenced by vignettes featuring three creepy girls in a playground, praying and proclaiming “he’s here,” rode to the ring a metal steed, with a whole new look – The American Bad Ass debuted looking for violent retribution, and getting it but inadvertently handing victory to The Game in the process.
8 'Taker-Roonie – Raw, August 15, 2002
The lightest memory on this list comes in the form of a moment from the Raw After the Bell DVD. What started as an exchange between The American Bad Ass demanding Booker T gives the Seattle crowd what they want – a Spinaroonie, saw the rib turn on itself as Booker T would then get The Deadman to pop slightly and try to get The Phenom to actually completely break kayfabe and bust a move himself. Visibly getting a kick out of Booker’s attempt was fun enough but then The Rock came out to try and convince Big Evil. Then Triple H would join the insanity and question 'Taker’s manhood, looking to see “Dead Man Spinning.” It was definitely not a violent moment in their bitter rivalry, but certainly a funny one. Even though we got to see a Vincearoonie, Triple H would eat a Chokeslam, saving The Undertaker from having to dance.
7 On the Road to Hell – Raw, March 19, 2012
With two weeks left until their epic clash inside Hell in a Cell, The Cerebral Assassin and The Phenom met in the ring at Raw, with special guest referee Shawn Michaels right in the thick of everything. Triple H would reiterate that their match at WrestleMania XXVIII was destiny – the 25th Hell in a Cell match, a match that both men excelled at and where Triple H admitted he learned it was where he learned how destroy men’s careers. The Undertaker explained that it wasn’t just mind, body, and soul Triple H was putting on the line, it was his career, his family, and even his life was on the line when trying to end the Streak. Triple H wasn’t backing down, looking to give The Undertaker a fitting end he deserved. But in the game of mind games one–upsmanship…The Phenom got the last word here, telling Triple H that HBK was better.
6 Triple H and HBK's Pact – Raw, March 28, 2011
While both ‘Taker and Triple H were stalwarts of the Attitude Era, Triple H seemed to have not only known but had reconciled with the fact that one day, maybe not anytime soon but one day, he’d have to hang up his tights. Even though they faced off once before at the Show of Shows (more on that later), Triple H and The Undertaker were both now ten years older and looking at the twilight of their careers. Triple H would acknowledge that at this point in his career he had done everything and only one challenge remained – end The Streak. He let The Undertaker in on a deal that he and HBK once made with each other. That if at any point, either man thought the other went past their prime; the other would let them know by ending their career. Triple H would tell The Phenom, that for the Deadman, “it’s time.”
5 No Holds Barred – WrestleMania XXVII
When Roman Gladiators surround the stage to the sound of Metallica’s For Whom the Bell Tolls signaling the arrival of Triple H, you know that you’re about to witness a war the likes the Showcase of the Immortals has never seen. True HBK and The Deadman had put on classics, but The Phenom and The Game were more evenly matched as far as brutality goes. Their match could only be a No Holds Barred dogfight to see who would be the Last Outlaw. The two legends demolished each other for nearly thirty minutes and The Game would do everything in his power to defeat the Lord of the Darkness, but to paraphrase Johnny Cash’s song, there’s no grave that could keep The Undertaker down. In the end he was victorious, but had been given a beating so intense, he was carted off for the only time in his career.
4 The Trilogy Begins – WrestleMania X-Seven
From a match standpoint, the first WrestleMania encounter between The Undertaker and Triple H might be the best one. Which makes it a little jarring the match wasn’t mentioned during their later ‘Mania matches. Nevertheless, The American Bad Ass and The Cerebral Assassin’s collision course had some serious bad road to get there. Moments like Triple H destroying The Deadman’s bike and some more strenuous Stephanie terrorizing by The Undertaker, this time in the form of having his brother Kane threaten to drop her from the rafters if he didn’t get this match made the encounter that much more personal. As for the match itself – remember that 2001 Triple H was simply the best wrestler in the world and The Undertaker’s Big Evil had breathed new life into his career. It was a marquee grudge match that featured a brawl that spilled out into the Reliant Astrodome and a sadistic Choke Slam off the camera tower to the concrete.
3 Best Tombstone Ever – Shotgun Saturday Night, February 8, 1997
Back in the early days of the Attitude Era, WWE tried a new kind of show. Shotgun Saturday Night would be the WWE’s way of testing the waters of how far they could go, since they were on Saturday night, while still keeping Raw slightly more wholesome. SSN’s broadcast team included Brian Pillman, to give you an idea of how crazy the show was. Another idea was that on this particular episode, the action emanated from Penn Station. One of, if not the largest commuter train station in the world. One fateful weekend, then Intercontinental Champion, Triple H would arrive to Penn in a limo but leave via the escalator as The Undertaker would deliver a Tombstone right onto the moving walkway.
2 The End of an Era – WrestleMania XXVIII
After suffering a beating that saw The Phenom stretchered out of WrestleMania XXVII, The Undertaker demanded a rematch one year later. Triple H, now the on–screen boss originally refused, he had to do what was best for business and not end The Streak. But The Deadman would not relent, leaving The Game no choice but to accept with one stipulation – they would do battle within the confines of a match they both knew all too well, Hell in a Cell. Throw in Shawn Michaels as the guest referee and the intrigue and intensity would be higher than it ever was for their last battle, yes, the End of an Era. The true end of the Attitude Era as its two remaining biggest stars would do all they could to obliterate each other, with the same result as last year – a victorious Deadman but with one difference, this time Triple H was the one who could barely stand. HBK and ‘Taker would help him up and out of the ring and the three WWE stalwarts, who stood by Vince and the WWE during the company’s darkest time would share a tender embrace to end their long standing rivalry.
1 Silent Stare – Raw, February 21, 2011
For weeks, WWE fans saw vignettes of a shack in the pouring rain with the date inscribed, 02/21/11. Speculation was abound as to what would happen on that date and it led to two names, Sting’s debut or The Undertaker’s return. As we know, it would be the return of The Phenom, who would stalk to the ring of Monday Night Raw as he had done for years. But before he could state why he had come back, Lemmy’s voice cranked through the crowd, signaling another return – The Game’s. Triple H would come to the ring and the two icons stared each other down. Not a word was needed to be said. Triple H would look to the WrestleMania sign and then to The Deadman. The message was clear and the challenge was issued. It is still one of the most memorable moments in Raw history, and the most memorable in these two legend’s storied rivalry, no need for any braggadocios promos, just two outlaws from a bygone era stating their claim as to who is the best ever.