3. The Undertaker vs. Big Boss Man - WrestleMania XV
http://www.youtube.com/watch?v=lvatrRIruSg Undertaker's second appearance on this list is undoubtedly his worst WrestleMania match and many would argue the worst match of his entire career. This heel vs. heel battle - a rarity, especially for WrestleMania - featured the head of one heel faction going toe-to-toe with chief lackey (or 'head of security' as he was known) of another. It began at the start of the year, as Vince McMahon's Corporation wanted to prevent rebellion from the likes of Steve Austin, DX and eventually - the Ministry of Darkness. At the 'darkest' and most sinister stage of his career, Undertaker wanted to rid the company of the boss, so McMahon set up a Hell in a Cell match for his enforcer and the Phenom at WrestleMania. The storyline barely warranted using the revered structure. There was absolutely no chance of this matching the heights achieved in the first two Hell in a Cell matches - which begs the question why even bother? At this stage in his career, Boss Man was already well past his prime and on the decline, while Undertaker wasn't in good shape and would eventually need surgery by the end of the year. Gaining interest and some extra buys was all this could hope to achieve even if it meant hurting the reputation and aura the gimmick match had. The dull and lifeless battle lasted less than 10 minutes as the two staggered around the cell to the boredom of an indifferent crowd. Even WWE hate it so much that it's the only Hell In A Cell bout that didn't make it on the dedicated DVD. Even the Raw battles made it on the disc! The only thing from the match that people would remember was the imagery of Boss Man being hung post-match, something that has become a little awkward to watch following his death. Despite being at the peak of its popularity in the Attitude era, WWE served up a truly horrible WrestleMania in 1999 with little redeeming qualities - highlighted no more so than with this hell.