#2 Shawn Michaels
The road to WrestleMania's 25th Anniversary saw Shawn Michaels challenge The Undertaker to a match at The Grandest Stage Of Them All. The reasoning behind Michaels' challenge was the fact that Undertaker had never defeated him in a singles match. This included the first-ever Hell in a Cell match in 1997, which Michaels won after interference from a debuting Kane.
Also read: 5 times Eric Bischoff and Paul Heyman clashed in WWE
On an edition of Raw, 20 days before 'Mania, Taker teamed up with Shawn Michaels to take on the villainous duo of Vladimir Kozlov and JBL. The ending saw Michaels tagging himself in and stealing a quick pin on JBL. This angered The Undertaker to no end and he chased Michaels up the ramp. Michaels took advantage of an unsuspecting Taker and hit him with the Sweet Chin Music. Unfortunately for him, The Deadman won the 'Mania bout, and did the same a year ago, leading to Michaels' retirement.