The Undertaker: 5 WrestleMania matches that should have been against different opponents

#3. WrestleMania 15 vs. Big Boss Man

The Undertaker competes against the Big Bossman at WrestleMania XV

Should have wrestled: Stone Cold Steve Austin and The Rock

During this time in the The Undertaker's career, he was a menacing heel trying to dominate the company during his WWE Championship feud with Steve Austin. In the quest absolute dominance in the company, Undertaker turned heel and made a mission to take control of WWE from Vince McMahon. Despite being in a bitter rivalry with McMahon, Austin found it in his heart to protect his boss and rival due to tndertaker's tormenting of Vince's daughter, Stephanie. The feud between Undertaker and Vince led to a Hell in a Cell match against The Bossman at WrestleMania XV.

Wait. What?

This match made little sense in the overall storyline arc. Although Big Bossman was generally a notable name, a WrestleMania match against Undertaker was just not very fitting at this point of his career. Both Bossman and Undertaker were heels, so the fans were forced to pick from the lesser of two evils, esentially.

Additionally, the match was clearly going to be in The Undertaker's favor, and it did not do much to help his character. They attempted to make his character even more devious by literally hanging Bossman by a noose, but it came off more hokey than devious.

At the time, Steve Austin was occupied in a match against The Rock at WrestleMania. However, Undertaker being inserted into that match, and winning the title, would have been a perfect extension of the stories being told at the time.