10. Bret Hart vs. Shawn Michaels (Wrestlemania XII)
You either love the Iron Man Match or you hate it vehemently, there’s really no in-between. The whole premise was a major gamble by the then WWF, but was necessary due to a depleted roster. The effort put forth by both guys was remarkable and was a throwback to a bygone era. While this one certainly isn’t for everyone, it’s still a monumental achievement.
9. Shawn Michaels vs. Razor Ramon (Wrestlemania X)
There were ladder matches before this one, but the tilt between Shawn Michaels and Razor Ramon revolutionized the match and the WWE forever. This one was much more than just high spots, as the two Hall of Famers crafted an intricate and compelling story, set amidst the most dangerous match ever seen (at the time).
8. TLC II (Wrestlemania XVII)
From a match that revolutionized the ladder match…to a match that revolutionized the ladder match. This one was the culmination of a brutal series of tag-team ladder matches that began in 1999. Those contests set the stage for a stunt show of the highest degree at Wrestlemania XVII. The match featured some of the most ridiculous high spots in federation history, many of which have not been topped to this day.
7. Triple H vs. Shawn Michaels vs. Chris Benoit (Wrestlemania XX)
Triple threat matches are a tricky proposition, especially main eventing “The Show of Shows.” If three men could do it, Triple H, Shawn Michaels, and Chris Benoit were those individuals. The match was a masterwork in storytelling and drama. It was booked perfectly and executed flawlessly. The ending is bittersweet now, given the tragedy of Chris Benoit.
6. Ricky Steamboat vs. Randy Savage (Wrestlemania III)
If you’re a fan of the current style of pro wrestling, you have to pay your respects to this incredible match. Randy Savage and Ricky Steamboat showed athleticism and skills that few had seen up to that point in time. These two legends elevated the sport and made the Intercontinental Title must-see TV.
5. Shawn Michaels vs. Kurt Angle (Wrestlemania XXI)
Shawn Michaels vs. Kurt Angle was a dream match several years before it came to the fruition. Both stand as two of the best in-ring performers in the history of wrestling. The match more than lived up to the hype, as both were firing on all cylinders. The ending was heart-pounding and perfect.
4. Steve Austin vs. Bret Hart (Wrestlemania XIII)
Wrestlemania XIII was largely a disaster. One of the only saving graces was the remarkable submission match between a prime Bret Hart and peaking Steve Austin. The match was absolutely brutal and was a preview of what The Attitude Era would later become. The double turn at the end was masterful.
3. Bret Hart vs. Owen Hart (Wrestlemania X)
No opening match in Wrestlemania history can stand up to the technical classic authored by brothers Bret and Owen Hart. This one was a perfect mix of supreme athleticism and storytelling, that would even make a staunch cynic believe in pro wrestling. The ending was a shocker, but it made sense.
2. Steve Austin vs. Rock (Wrestlemania XVII)
No WWE title match has ever matched the greatness of the Wrestlemania XVII finale. In early 2001, wrestling was at its apex. The Rock and Stone Cold Steve Austin were both at an all-time high in popularity. While a rematch from two years earlier, this one was a major happening in front of a hot Astrodome. The ending was a bit heavy-handed, but the match itself was pure magic.
1. Shawn Michaels vs. Undertaker (Wrestlemania XXV)
The Undertaker and Shawn Michaels have always had amazing chemistry in the ring. This author is still of the opinion that their Hell in a Cell match is the greatest in-ring performance in wrestling history. Not far behind, is the amazing story told at Wrestlemania XXV between these two men. The match had a little bit of everything and helped elevate an otherwise disappointing show.