Shane McMahon and The Undertaker have had a heated history in the WWE. The last time these two Superstars competed was at WrestleMania 32 in a Hell in A Cell Match. Their match is remembered for Shane McMahon's leap that he took from the top of the cell only for The Undertaker to slide away.
The stipulation of the match between Shane McMahon and The Undertaker at WrestleMania 32 was that had Shane McMahon won, he would have gained control of WWE RAW and The Undertaker would never compete at WrestleMania again. The match ended after The Undertaker hit Shane McMahon with the Tombstone Piledriver for the three count.
Why did Shane McMahon vs The Undertaker take place at WrestleMania 32?
At the After The Bell Podcast, held by Corey Graves, "The Best In The World" spoke about his match against The Undertaker at WrestleMania 32.
"Taker needed an opponent for WrestleMania and needed to be special, and there was talks even back then. I really thought it may be, again, a one and done. So I got the call from Taker saying, 'hey, would you ever consider this? I was like, 'huh, well, let me think about it.' About 10 minutes later, I get a call from my dad. He's like, 'well, congratulations. This is what we're doing. What do you think?' I was like, it doesn't sound like I'm thinking much. In typical Vince fashion, he's like, 'we want you to think about this.' I was like alright and then really started coming up with the creative. I said well, if it's gonna be what I think it's going to be, than can we do Hell in a Cell? Can we do this and we have to make sure the storyline more than anything is right. Otherwise, it's just a mash, so why are you emotionally, this is one thing, again going back to what I've learned throughout the years, in any match I've ever ever done, I've always had some crazy stuff that happens from time to time, but it's really the emotional story of why. What got us there and what you do telling the physical story once you're in the match" (h/t Wrestling Inc)
We just asked The Shockmaster about Vince McMahon's retirement here