5 Biggest Regrets of The Undertaker's WWE career

#3 The Undertaker hanging the Big Boss Man

Back in the day, WWE was known to do some crazy things on its TV programming, something that would be unthinkable in the PG era. One such moment took place at WrestleMania 15 in 1999, where The Undertaker took on the Big Boss Man inside Hell in a Cell. While the match in itself wasn't one of the better ones in The Undertaker's career, what happened afterward made for one of the most uncomfortable moments in WWE history.

For those that have not seen it, The Undertaker went on to hang the Big Boss Man from the cage by a noose, in front of thousands of people in the arena, not to mention the millions watching at home. While it might sound like a cool idea on paper to further establish the dangerous and deadly character of the Phenom, hanging his opponent on a live pay-per-view was a little too much.

Bruce Prichard later revealed that the Big Boss Man was wearing a harness under his outfit that they hooked him onto. However, this still doesn't justify WWE trying to pull off that segment!