10 WWE Worst WrestleMania Gimmick Matches
2. The Undertaker vs Big Boss Man (WrestleMania XV)
During his legendary career, The Undertaker has taken part in some of the finest Hell In A Cell matches we’re ever likely to see, but his record is by no means unblemished. This oh-so-Attitude Era match sees the Deadman step inside the structure with The Corporation’s own head of security for 10 minutes of nothing.
There are problems from the off in the form of the video package, which focuses exclusively on ‘Taker vs Vince McMahon, with Bossman barely getting a look-in. That heatless quality extends to the match. These two big men were veterans and immensely talented, but there’s nothing to latch onto here, neither seeming interested in doing much beyond walking and punching
The crowd don’t even try to get into the match. Goofiness abounds as Bossman handcuffs Undertaker to the cage only for the cuffs to immediately break. Eventually after a long 10 minutes Undertaker hits a Tombstone and we’re done.
What follows is the infamous spot of Undertaker hanging Bossman, and while it’s a bonkers visual, it’s easily the most engaging part of the match. Used to end a feud with some actual venom, it would still be quite stupid, but effective.