The Undertaker's 14 WWE Hell In A Cell Matches Ranked From Worst To Best
12. Vs. Big Boss Man - WrestleMania XV
In spite of the fact that the Ministry of Darkness was all over Raw in early 1999, torturing Vince McMahon because they could, the creative team seemed to have nothing for its leader come WrestleMania. You'd think stalking the McMahons would warrant main-event violence, but instead 'Taker was put inside Hell In A Cell with the Corporation's Head of Security: The Big Boss Man.
It could have worked, in theory, but it ended up being little more than filler. The brawl was fun in the beginning but it just raged on for 9 minutes with no real flow, and - cell aside - it basically felt like a match you'd watch on a random episode of Raw at the time.
Designed purely for the post-match hanging spot, this one was a complete and utter disservice to both men - and it certainly didn't help that they were both heel at the time, so the audience was completely disinterested for most of it.