Shawn Michaels Confirms WrestleMania 26 Match with The Undertaker as His True WWE Farewell

Despite wrestling at Crown Jewel 2018 alongside Triple H, Shawn Michaels considers his WrestleMania 26 bout to be his swansong

Shawn Michaels Confirms WrestleMania 26 Match with The Undertaker as His True WWE Farewell

Shawn Michaels and The Undertaker (via WWE)

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Nearly four years after dropping the WWE Championship to Stone Cold Steve Austin at WrestleMania 14 in 1998, many fans believed Shawn Michaels’ in-ring career was over. Years of back injuries and personal struggles had taken a heavy toll, and HBK no longer looked like the same man who dominated the early 1990s. But everything changed at SummerSlam 2002. 

Michaels made a shocking comeback against Triple H and delivered an all-time classic, proving he had conquered his demons and could still perform at the highest level. What seemed like a one-night return turned into a full-time second chapter, as he wrestled until 2010, giving him not one, but two Hall of Fame-worthy careers before and after his injury. 

‘Mr. WrestleMania’ more than lived up to his nickname. From his groundbreaking ladder match with Razor Ramon at WrestleMania X to his technical masterclass with Kurt Angle at WrestleMania 21 to his unforgettable battle with The Undertaker at WrestleMania 25, often hailed as the greatest WWE match ever, Michaels built a legacy of WrestleMania classics. 

However, he considers his Streak vs. Career showdown with Taker at WrestleMania 26 in 2010 to be his true farewell, despite stepping back into the ring once more in 2018. For years, it looked like Michaels would be one of the few legends in professional wrestling to actually stick to his retirement. 

But in 2018, WWE’s blockbuster deal with Saudi Arabia brought him back for one more match at Crown Jewel. Teaming up with Triple H, the two reformed D-Generation X to take on The Brothers of Destruction, Undertaker, and Kane. What was meant to be a dream match turned into a disappointment. 

The bout fell flat, and even Michaels later admitted it wasn’t his proudest moment. He called it a cheat day, insisting it wasn’t about money but rather a rare opportunity he thought would never happen again. However, when he learned that ‘The Deadman’ had been struggling with finding the right way to close out his own career, HBK expressed regret for not taking the match as seriously as his rival did.

Speaking on Chris Van Vliet’s Insight, the two-time Hall of Famer was asked why he still considers his WrestleMania 26 clash as his final match. HBK explained that his 2010 bout was his true farewell because, unlike the Saudi Arabia tag match, it was the ‘Heartbreak Kid’ in action, not just Shawn Michaels the person.

It’s that one with Undertaker [at WrestleMania 26]. Because the other one it was a tag match, it was DX, and I feel kind of bad, because I don’t mean it in a negative way, but that was just sort of like, I don’t know.

Shawn Michaels via Chris Van Vliet’s Insight

Michaels clarified that his true athletic prime and the ability to steal the show ended in 2010 with his fairytale ending with the real-life Mark Callaway. 

HBK and Mr. WrestleMania, The Showstopper, whatever, that ended with Taker at WrestleMania, because I still came back and refereed the match between Hunter and Taker, again, and will always play a role in the WWE.

Shawn Michaels via Chris Van Vliet’s Insight

Michaels further clarified that he doesn’t see the Crown Jewel tag team match as part of his official career. In his view, it wasn’t the ‘Heartbreak Kid’ performing, but simply himself having fun with friends in the ring. 

Shawn Michaels weighs in on his initial hesitation about his theme song that later became part of his identity

Now officially retired from in-ring competition, Shawn Michaels has been in charge of running NXT since 2022. But whenever his theme song plays, crowds always go berserk and have the same reaction that they used to have when HBK was still performing at the top level. However, it is interesting to note that the WWE Hall of Famer did not like his theme song at first. 

Shawn Michaels as the Heart Break Kid
Shawn Michaels as the Heartbreak Kid (via WWE)

In the same interview with Chris Van Vliet, HBK admitted that when the song first dropped, he couldn’t really connect it to the character that he was aiming to portray inside the ring. As a singles star, he imagined himself as more of an action-hero type, like the character Kevin Nash often described, cigar in his mouth, machine gun in his hand, and the girl by his side. Instead, his character was far from that image.

It wasn’t until he was paired with Sensational Sherri and leaned into the boy toy persona from the song that he began to embrace it. This shift helped him fully develop the Heartbreak Kid character that would define his career. Michaels recalled feeling self-conscious about recording the song himself because of his deep voice and inability to hit high notes. 

However, Jimmy Hart reassured him they could make it sound great. When the theme eventually transitioned from Sherri singing it to Michaels, it became a defining part of his identity. Looking back, he found the whole idea ludicrous since it wasn’t how he envisioned his character. 

He believed he would have fit better with a grittier persona later in his career, but at the time, he had to lean into the over-the-top role, and it ultimately shaped HBK into the legend he became.

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