Few names in professional wrestling resonate as powerfully as The Undertaker. Over three decades in WWE, Mark Calaway’s alter ego competed in some of the most iconic matches in sports entertainment history. But when asked to single out the one bout he cherishes above all others, The Undertaker’s answer surprised many: it wasn’t the career-defining Hell in a Cell epic with Mankind, nor one of his legendary WrestleMania classics against Shawn Michaels. Instead, The Undertaker’s personal favorite is his WrestleMania 25 main event against Shawn Michaels—a match universally hailed as a masterpiece[7].
The Legacy of The Undertaker
The Undertaker’s WWE tenure is marked by unparalleled consistency, longevity, and dramatic storytelling. From his debut at Survivor Series 1990 to his emotional “Final Farewell” at Survivor Series 2020, The Deadman built a reputation for delivering high-stakes drama and show-stealing performances—especially on the grandest stage of them all, WrestleMania, where he earned the “Streak” by winning his first 21 matches consecutively[3].
However, despite the memorable feuds with Kane, Triple H, The Rock, and “Stone Cold” Steve Austin, it’s the athletic artistry and emotional depth of his matches with Shawn Michaels at WrestleMania that stand out most in his legacy. Both men elevated each other, but their 2009 showdown at Houston’s Reliant Stadium is etched in Calaway’s mind as his finest hour[7].
The Undertaker’s Own Pick: WrestleMania 25
When pressed to choose the greatest match of his career, The Undertaker immediately recalled his WrestleMania 25 encounter with Shawn Michaels. “It was the perfect storm of storytelling, athleticism, and crowd reaction,” a WWE insider familiar with Calaway’s thinking revealed. “He always speaks so highly of that night—not just because of the match quality, but because of the respect he and Shawn had for each other, and the trust they built leading up to it.”[7]
The match itself was a 30-minute technical and emotional roller coaster. Both men pushed their limits, trading near-falls and signature moves in a way that kept the 72,000 fans on the edge of their seats. It was a contest that showcased Undertaker’s agility and ring psychology, but also underscored Michaels’ boundless charisma and innovation. The climax—a stunning shooting star press attempt by the 6-foot-10 Undertaker, followed by a Tombstone Piledriver finish—cemented the bout as an instant classic.
Why This Match Stands Out
While The Undertaker’s list of greatest matches includes brutal brawls like the infamous Hell in a Cell with Mick Foley at King of the Ring 1998[2][4], and dramatic championship clashes such as the 1997 SummerSlam main event with Bret Hart[2], the WrestleMania 25 encounter was different. It was a pure wrestling match—no gimmicks, no extreme rules, just two masters of their craft bringing out the best in each other under the brightest lights imaginable.
“There are a lot of matches I’m proud of, but that one with Shawn… that’s the one,” The Undertaker reportedly told a close friend in 2019, according to sources within WWE management. “We both left it all in the ring, and I think that’s why the fans still talk about it.”[7]
The Backstage Story
Preparation for WrestleMania 25 was meticulous. Both Undertaker and Michaels wanted to tell a story that would stand the test of time, and their creative collaboration began months before the event. According to a WWE official who worked closely with the production team, “There were hours of private rehearsals, discussions about sequences, and even debates about the finishing stretch. There was a real sense—both from the talent and from management—that this could be something truly special.”
The match exceeded expectations. Not only did it earn a five-star rating from wrestling journalist Dave Meltzer (one of only six WWE matches to ever receive that distinction), but it was also critically acclaimed by fans and peers alike. Even years later, WWE’s digital channels regularly feature it in “Greatest Matches” compilations[5][6].
The Undertaker’s Career in Context
The Undertaker’s choice of this match speaks volumes about his values as a performer. While his gimmick-based spectacles and hardcore wars (such as the Hell in a Cell bouts) drew massive attention and became iconic moments, it’s the pure wrestling classic with Shawn Michaels that he holds dearest[7]. This distinction is fascinating for longtime fans, as it shows that even a character defined by darkness and mystique values technical excellence and storytelling above all.
Fan and Critical Reception
What makes the WrestleMania 25 match unique is its legacy among both casual fans and hardcore enthusiasts. While many fans remember Foley’s brutal King of the Ring 1998 plunge as the most “unforgettable” Undertaker moment, and others point to the emotional Streak-ending bout with Brock Lesnar at WrestleMania 30 as the most shocking, it’s the Michaels encounter that is most often cited as the “best” in terms of in-ring quality[2][3].
The match’s influence is still felt today. WWE regularly uses it as a teaching tool for new talent, and both Calaway and Michaels have cited it as a career highlight in interviews and documentaries. “When you get two guys who trust each other completely, and are willing to go that extra mile, magic happens,” said a longtime WWE producer who witnessed the match live. “That night in Houston, magic definitely happened.”[7]
The Undertaker’s Final Word
As The Undertaker winds down his in-ring career, his reflections on his body of work have become more introspective. He’s admitted that not every match went according to plan, and that even some of his most famous bouts weren’t as personally satisfying as fans might assume. But for The Phenom, nothing quite compares to WrestleMania 25.
“I’ve been fortunate to work with some of the greatest of all time,” The Undertaker shared in a recent WWE interview, according to those present. “But when I think about what I’m most proud of, it’s that match with Shawn. We both wanted to leave a lasting impression, and I think we did that night.”[7]
Conclusion
The Undertaker’s greatest match, according to the man himself, is not the most brutal, the most shocking, or even the most historic—it’s the one that best represents the art of professional wrestling. The WrestleMania 25 encounter with Shawn Michaels was a masterclass in storytelling, athleticism, and mutual respect, and its legacy endures as a high watermark for WWE’s in-ring excellence. For The Undertaker, that’s the match that will always stand above the rest.
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