They’re the best of friends and the worst of enemies - the Heartbreak Kid and the Cerebral Assassin. The Icon and The Game. Shawn Michaels and Triple H. Ever since Hunter arrived in late 1995, the pair, along with Diesel, Razor, and The Kid, were as thick as thieves. Once the latter three hightailed it for WCW, it left Shawn the then-champion and Hunter, eating crow for the Curtain Call we’re booked to set the world on fire, until the Call happened.
Nearly a year later, DX formed. Two years later, Shawn was done, and Triple H rose to immeasurable lengths of power. Then Shawn returned and the war between the two got underway. The would eventually reform DX, but until that day and even sometimes after it, they beat each other from pillar to post and beyond.
10 SummerSlam 2002
It was the comeback match fans had waited four years for. Shawn Michaels returned and returned to form in an Unsanctioned Match against Triple H at SummerSlam 2002. Not only was the match phenomenal, it began the process to bring back Shawn Michaels for another eight years, cementing his place at the greatest of all time. The two destroy each other and used any and all plunder they could find, including HBK performing his patented Elbow Drop off of a ladder through a table. It was a triumphant return for the Showstopper, even if HHH nailed him after the match.
9 Royal Rumble 2004
With a chance at headlong WrestleMania XX in Madison Square Garden as WWE Champion on the line, Triple H and Shawn Michaels attempted to destroy each other. The 2004 Royal Rumble match saw the two battle in a Last Man Standing match.
RELATED: Triple H: 5 Reasons He Was Better In DX (& 5 Reasons He Was Better In Evolution)
After the back and forth contest that saw each man narrowly escape losing finally saw both men just collapse in a heap, with neither able to answer the ten count.
8 Armageddon 2002
A barbed-wire 2x4 lit on fire was just part of the first fall in the Three Stages Of Hell match between Michaels and Triple H at Armageddon 2002. After Triple H won the first fall, a cage was lowered down for the second fall of one of the most brutal contests these two ever had. The second fall was won by HBK, who splashed the Game from the top of the cage through a table. Tables were a massive part of this war and played a part in the climax of the third and deciding fall. Triple H shoved his former friend off of a ladder into several tables in order to grab his title and once again be the Man.
7 Raw 05/13/1996
In his first reign as champion, the original plan was for Shawn to have a lengthy feud with the winner of the King Of The Ring, Hunter Hearst Helmsley. Then the Curtain Call happened, Hunter lost out on winning the tournament and warring with his buddy. Both of those events would eventually happen. But in 1996, we only received this gem from Monday Night War. The match was a good technical match, and interesting to see before both men changed up their styles years later in the fights to come.
6 Survivor Series 2002
In this storyline, Raw GM Eric Bischoff announced the first-ever Elimination Chamber to main event the 2002 Survivor Series. Triple H would defend the WWE Heavyweight Championship against Kane, Booker T, Jericho, Van Dam, and HBK.
RELATED: Shawn Michaels' 10 Best Royal Rumble Performances, Ranked
By this point in his return, Shawn wanted nothing more than to make sure Triple H did not walk out of the Chamber as the man. No one actually pegged HBK to win the match. But that’s exactly what he did, closing the next chapter on their feud.
5 Survivor Series 2009
Despite now being unified once again as DX, Michaels and HHH once again found themselves waging war for the WWE title. Only this time, John Cena was the defending champion. Despite heading to the ring together, HBK immediately Superkicked the Game right out of the match’s opening minutes. As usual with these two, their egos outweighed their friendship and Cena was able to take advantage and eventually deliver the AA on HBK and into HHH for the pin.
4 Raw 12/29/2003
It had been six years since the Heartbreak Kid was in his hometown, challenging for the WWE title. When Raw emerged from San Antonio, Shawn looked to rekindle some of the old magic as he once again took on the Game for the strap. The raw (no pun intended) emotion that always existed between these two was only heightened HBK nearly kicked Hunter’s head off for the 1-2-3. The hometown crowd nearly rioted when Eric Bischoff would award the match to the Game, since both men’s shoulders were on the mat for the three count.
3 SummerSlam 2003
Less than a year after six superstars were encased inside of the Elimination Chamber, Triple H, HBK, Goldberg, Randy Orton, Kevin Nash, and Chris Jericho all stepped inside of Satan’s Structure for the richest prize in the industry. The story of this match was more building up to the eventual singles match between Goldberg and Triple H. But that doesn’t mean that HBK didn’t get his licks in in the Game. Michael delivered a Superkick to Helmsley the instant his pod opened and took him out of the match for a few moments.
2 Badd Blood 2004
Nearly an hour of destroying each other is what happened at the last ever Badd Blood event in 2004. Shawn Michaels and Triple H stepped inside the match that HBK helped to make famous, Hell In A Cell. What haven’t these two done to each other?
Pretty much nothing, only now they pulled out all of the stops inside the Cell. With no titles on the line, it took Triple H not one, but two Pedigrees to take out HBK.
1 Taboo Tuesday 2004
With the fans getting to vote on the fates of WWE superstars, the universe chose Shawn Michaels to take on Triple H for the WWE title. As usual during this era, Triple H’s Reign Of Terror, he would again find a way to win, thanks to Edge, sore from losing the fan vote interfered and speared HBK.
