8. The Big Boss Man (Hell In A Cell Match Vs The Undertaker) - Wrestlemania 15
The Big Boss Man occupies a special place in the hearts of wrestling fans of two generations. He will likely either be remembered for his first period with WWF during the late 1980's/early 1990's, playing a prison guard character, or for his run during the Attitude Era, where he wore black SWAT gear (a look that heavily inspired the ring attire of The Shield) and was a member of The Corporation. It was during this run that he found most success, winning the Tag Team Championship and Hardcore Title. He even engaged in a controversial feud with The Big Show over the WWF Title for a short period, but arguably his most high profile match-up came at Wrestlemania 15 in 1999: a Hell In A Cell match against The Undertaker. The match itself is entirely forgettable, clocking in at under ten minutes in length. It wasn't even the main event, unlike all other Cell matches up until that point, which should have given fans the clue that something out of the ordinary was about to happen. By the time The Brood descended from the rafters and passed a noose through the roof of the cell, allowing Paul Bearer to raise it and 'hang' The Boss Man, fans were understandably aghast and mystified at this turn of events. At least it then made sense why a midcard talent had been booked in a huge match at The Showcase Of The Immortals: it was a stunt, rather than an actual wrestling contest.
