The Undertaker's 23 WrestleMania Matches - From Worst To Best

15. Jake Roberts (WrestleMania VIII)

The Undertaker's WrestleMania VIII match against Jake "The Snake" Roberts may be the most underrated of any on this list. Sure, there is nothing special about it from an action standpoint. In fact, from that perspective, it was pretty awful. But the psychology and story behind it helped elevate it to out of the depths of this list and into a respectable showing at number 15. Roberts was the most despicable wrestler in the world in 1992. His actions against Randy Savage and Miss Elizabeth were so disgusting that Undertaker stood up to him, necessitating The Phenom's babyface turn. No matter how vile a villain he may have been, though, he proved no match for the most intimidating force in professional wrestling. No matter what he threw at The Deadman, Roberts found himself more and more frustrated by the lack of effect it had on him. Two DDTs were not even successful. Instead, The Phenom sat up, delivered a Tombstone on the arena floor, rolled him in the ring and scored the pinfall victory. Like the Snuka match a year earlier, this one saw Undertaker add to his budding reputation as the most intimidating performer on the roster as he tore through a respected veteran and future Hall of Fame inductee en route to victory number two.