The 15 Most Iconic Triple H And Shawn Michaels Pictures Of All Time

With the recent news of Shawn Michaels joining his best friend down in NXT, we couldn’t help but to go back down memory lane and look back at some of the most ionic images of the two stars, spanning the last two decades from 1995 till this very day.

The two Superstars have done it all side by side, from creating one of the best factions in WWE history to becoming bitter enemies, everything they did together was absolute gold. They helped to usher in the Attitude era during the 90s and solidified the WWE’s program in the 2000s with an epic feud the left us fans with a variety of moments that we still look back on fondly today (like Shawn’s SummerSlam '02 return).

Now we get excited for a different reason; the impact they will make internally behind the scenes. Triple H has thrived to another level with NXT and we truly hope that Shawn can aid his best friend into taking things a step further. We truly cannot wait.

For now let’s celebrate these two great wrestlers by highlighting the most iconic pics of the two Superstars together. Here are 15 of the most iconic Triple H and Shawn Michaels pictures. Enjoy!


15 Before DX

Before the two would unite and form one of the greatest factions in pro wrestling history, the career trajectories for the two were vastly different. HBK was on top of the WWE as the face of the company, while Triple H struggled to find his feet early on. Hunter signed his first WWE deal in 1995 and would go on to debut at SummerSlam defeating Bob Holly. Hunter was a student in the ring but an outcast at first behind the scenes, being labelled as a WCW guy.

Eventually things changed and Hunter became a part of the backstage group known as 'The Kliq'. He was still using an outdated gimmick as Hunter Hearse Helmsley, but he began to be booked differently because of the friendships he formed. He began to get included with some of the very best in the ring, like Shawn Michaels, as you can see in the picture above. Ultimately, the two would join forces and revolutionize the industry forever.

14 The Curtain Call

Quite surreal to think that an event that took place over two decades ago is still being discussed today on various wrestling media platforms. May 19th, 1996 is a date cemented in wrestling history, as it is when the business took a shocking turn. Kliq members Shawn Michaels, Triple H, Kevin Nash and Scott Hall, exposed the business in front of a Madison Square Garden crowd breaking kayfabe and hugging after a match. This was the first time heels and babyfaces were seen breaking kayfabe in a WWE ring.

With Nash and Hall leaving to WCW, and Shawn as the face of the company, Triple H suffered the brunt of the punishment. Although it is still unclear if Vince approved the idea or not, in a recent shoot interview, Scott Hall claims McMahon told them to do it, while other former Superstars disagree and claim the group was driven by their reckless ego. No matter what the case may be, it was a moment that will live on forever.

13 DX Begins TO Dominate

At that point in time it was exactly what the business needed, something edgy and in-your-face that was too good to turn away from. 1997 was a huge year in particular for Hunter’s rise to the top of the company. After sustaining a terrible run following The Curtain Call, Hunter was finally being pushed as a major player. He would win the 1997 King of the Ring tournament by defeating Mankind, which was a big deal during that era. As if that wasn’t enough months later the company would give him a massive push putting The Game side by side with the face of the company, Shawn Michaels. They would later be joined by Chyna and Rick Rude. The group found instant chemistry being known for their risky type of behaviors week in and week out.

The team would dominate the landscape of the entire WWE for the next several years with Triple H as a prominent player of the group.

12 Attitude, Attitude And More Attitude

At the time of WCW’s dominance over the WWE, Bischoff’s company was thriving using edgy storylines lead by Hogan and his fellow nWo mates. For a long time, the WWE just didn’t have a response and failed to modernize the company. McMahon had a constant reliance on the old guard which caused the company to feel stale and outdated.

The Kliq members had seen enough and sat down with McMahon one night demanding for an edgier program. Vince finally agreed and started to push the company into a different direction. DX was the first act to really push the envelope towards the Attitude Era; Hunter and Shawn pushed the most outrageous ideas which didn’t really please Vince all that much. Thankfully though, Vince Russo was by Vince’s side to encourage and approve of such drastic ideas.

Ultimately, what DX brought forward absolutely worked and thrived, whether it be wearing thongs on Christmas episodes or wearing wiper blade shields while talking to commissioner Slaughter; it just all worked during that time frame making the group the catalysts of the Attitude Era.

11 Dominating In And Out Of The Ring

What made DX so special was the fact that that they were as good in the ring, and as entertaining out of it on the microphone. The duo was able to back up everything they said with constant five star matches. For many wrestling enthusiasts, this is what separated DX from the nWo: their in-ring talent.

Michaels in particular was regarded as the best in-ring competitor in all of pro wrestling during that time, and is still regarded as one of the very best (if not THE best) to ever lace up the boots. During DX’s rise, HBK was absolutely thriving. He solidified his dominance by defeating the British Bulldog at One Night Only in England, claiming the European Championship. With both WWE Title and European Champion, Michaels became the first ever Grand Slam Champion in WWE history. He’d later give the European title to his partner Triple H, solidifying the group’s dominance and power.

10 The End

March 29th, 1998, was a difficult day and night to swallow for both HBK and Triple H. On that date, Michaels was set to take on Austin in the main event of WrestleMania XIV, but what made the bout so hard to swallow was knowing that it would be Shawn’s last match for a long time.

Shawn was nursing a severe back injury which he re-aggravated following a match against The Undertaker, months prior at the Royal Rumble. That mixed with simply burning out lead to a long hiatus for Shawn. With that in mind, Hunter was also unsure about his future with his partner being sidelined. It all looked very rocky.

Michaels would end up going through with the match, despite concerns that he wouldn’t. The story goes that Hunter literally had to dress him up for the match. Following the event Triple H relaunched DX the next night on Raw and never looked back, becoming the face of the industry after the departure of his fellow DX brother.

9 Shawn’s Brief Return

During his time away from the ring, Michaels struggled and was said to be very depressed. Hunter was making a name for himself while Shawn battled his own personal demons outside of the spotlight.

This eventually caused the WWE to call Shawn four months later. HBK would briefly appear as a guest commentator. The company would later take things a step further by giving Shawn a prominent role as the acting WWE Commissioner, taking the place of Sgt. Slaughter.

Shawn was fine in his role but never really seemed to be too invested in the idea. He flopped around for several months on-screen before the company finally decided to part ways with Michaels. He would hand over the role of Commissioner to Mick Foley, who would absolutely thrive in HBK’s spot. Following his departure Shawn would leave the company for a couple of years till his improbable return, which shocked the WWE universe.


8 The Comeback

After leaving the company for good in 2000, Michaels struggled to find a passion. He opened up his own wrestling school but would later rejoin the WWE in 2002, making a comeback that nobody saw coming.

His return was strictly intended as a manger, initially joining a watered down version of the nWo alongside his buddy Kevin Nash. After Kevin went down with an injury, HBK was called into action as a potential opponent for Triple H.

Shawn was approved by doctors and given the green light; the two former best friends would embark in a lengthy feud that is regarded as one of the best in WWE history. Their first match was arguably the best. It took place at SummerSlam in 2002, and it was Shawn’s first match in nearly four years.

The match was ultimately deemed 'match of the year caliber' with Shawn looking like he hadn’t missed a step. The entire match and building blocks leading up to the encounter were absolutely spectacularly done. It was all surreal to watch at the time.

7 Return Complete

Following the SummerSlam match, the WWE chose to continue the feud and for obvious reasons, it was a major hit. The next big PPV on the horizon during that point in 2002 was the Survivor Series; that year the event was a huge deal because of the fact that it took place in a sold out Madison Square Garden crowd in New York. The company was well aware that they needed something big and that is exactly what they did.

For the main event, Eric Bischoff booked the debut of the Elimination Chamber, a match that had never been seen before. The match required six participants and was made that much more interesting when the Championship was put on the line. To add to the intrigue of it all, the WWE decided to put HBK in the mix as well.

The match was a huge hit but the finish stole the show, as the roof nearly came off MSG when Michaels recorded the victory, pinning Triple H and capturing the World Heavyweight Championship. The title solidified his return and rightfully so, he was handed down by his best friend in Triple H. Michaels would later return the favor losing the Championship back to Hunter at the next PPV, Armageddon.

6 The Final Chapter

The ongoing rivalry between Triple H and Shawn Michaels was a joy to watch throughout 2002. The company decided to revive the feud in 2004, putting the two together in a final match for the WWE Championship at the Royal Rumble. Yes, the two would later face-off in a Triple Threat main event WrestleMania match, but this bout will forever be remembered as the end of the bitter in-ring rivalry.

The event took place in front of a hostile Philadelphia crowd, which as you probably know, isn’t afraid to speak their minds. This match was an absolute masterpiece met with so much respect by the crowd for the two. The 23 minute marathon match was a brutal blood bath mixed with some brutal strikes, weaponry and in-ring manoeuvres. The match ended the best way possible between the two as a draw, when both men were unable to get up from a ten count. The match stole the show and is remembered as the final chapter in what was a brilliant rivalry.

5 DX Returns

After sustaining a lengthy run as a heel (which started way back to 2002), the WWE finally decided to make Triple H a babyface in the summer of 06. How? Well, the only way to pull off something like that was with reuniting Degeneration-X.

The company teased a return for months prior. The crowd was really into it all and wanted the duo to finally reunite. The company agreed and put them together, officially relaunching DX on the June 12th, 2006 edition of Monday Night Raw.

For obvious reasons their second run wasn’t even close to the first but that was for a variety of reasons. The company was in a different era for one, and Shawn was now a Born Again Christian, so there was only so much he could have done. The humor was kind of corny but did appeal to a younger demographic. At the end of the day, it was just nice to see the two side by side once again.

4 The End Of An Era

WrestleMania will forever be regarded as Shawn’s yard to steal the show, so it was only right to book HBK’s final match against the man with the streak, The Undertaker. Both matches were absolute masterpieces. The final bout between the two came at WrestleMania XXVI, where Shawn declared that if he would not break the streak, he’d retire from the company.

Michaels would lose the match and has not wrestled since. In the following WrestleMania events, Triple H would try to avenge his best friend's loss by challenging The Undertaker. The two would fight for a third time at WrestleMania, this time in a Hell In A Cell match that saw HBK get called upon to be the special referee. The bout was another master class and ended with all three men atop the Mania ramp saluting the crowd as Michael Cole stressed the words “it’s the end of an era”. Truly a sight to behold.

3 Inducting His Best Friend

On the January 10th, 2011 edition of Monday Night Raw, the company announced the induction of Shawn Michaels into the Hall of Fame. Instantly you knew that only one man could make such an induction, and that was his best friend Triple H.

Shawn’s career was celebrated on that night as he etched his name into WWE royalty. The night was filled with emotions when looking back at HBK’s WWE run, which spanned all the way back to 1987 when he debuted as a Tag wrestler with The Rockers. Michaels left a legacy behind that will simply go untouched forever. He was arguably the greatest in-ring performer of all time and had a resume to back that up. Three time WWE Champion, one-time World Heavyweight Champion, two-time Royal Rumble winner (back-to-back), three-time IC Champion, six-time Tag Team Champion, European Champion and the first ever Grand Slam Champion. If that wasn’t enough, Shawn will always be remembered as Mr. WrestleMania. What an honour.

2 Reunited Down In NXT

Most recently another iconic picture was added to the mix with the announcement of HBK joining his best friend down in NXT. Hunter sent the wrestling community in a buzz when he posted a picture on his social media account of Michaels at the Performance Center down in Orlando. According to recent rumors, Michaels is currently in the process of relocating and heading down to Florida, moving next to the Performance Center permanently.

This news truly excited several fans. Shawn’s contributions will no doubt help Hunter even more. Triple H has excelled in his new life taking the developmental brand by storm. NXT is currently regarded as the WWE’s hottest commodity at the moment and something that just seems to be getting hotter year after year. Remarkable to think of the impact these two men made in the ring for years, and the impact they are about to make together out of it. Truly brilliant.

1 Best Friends Still Going Strong

In the world of professional wrestling, it’s really hard to find two performers that have been genuine best friends for all these years. In reality, there’s probably only a handful of Superstars that come to mind.

Hunter and Shawn have been close since the mid-90s, that’s over two decades of friendship. The guys have been through it all in and out of the ring, and it's pretty great to see how close they still are today, even with Hunter’s busy schedule. Stephanie herself admitted that when things get too hectic for Hunter she calls Shawn over to calm his best buddy down (still to this day). The two also speak and text on a daily basis.

A genuine friendship as such is really great and we hope to see it blossom even more with Shawn’s new role alongside Hunter down at the Performance Center. We can’t wait to see what these two have planned for all of us in the future. For now we sit back in anticipation!


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