WWE: 29 Iconic WrestleMania Moments

WrestleMania XV - Undertaker Hangs The Big Bossman

This was a dark time for WWE. They'd buried Taker alive at an In Your House PPV that year, and an Inferno Match followed shortly thereafter. The rest of the card at this Mania featured a Hardcore Match and the shoot disaster called the Brawl For All. How disturbingly fitting, then, that this year's iconic moment involves one of the most discomfiting images in all of WWE history.

The Undertaker was experimenting with a new persona, what with coming back from being buried alive. With Mideon, Viscera, and the Brood at his disposal, he formed the Ministry of Darkness, terrorizing Vince's Corporation and threatening its stability. The Boss Man was Vince's head of security, and so it seemed only fitting that Taker challenge him €“the match was contested in a Hell in a Cell. Aside from the structure itself being extreme, this match saw action from handcuffs, a nightstick, and a chair. After more fighting, Taker signals for The Brood to descend from the rafters. They dutifully rip open the ceiling of the cell, and lower a noose for Boss Man. Paul Bearer triggers the mechanism to raise the cell, subjecting the 20, 000 in attendance to what was likely their first public hanging. The whole process was long and drawn out, feeling at least as long as the match itself. As Taker's generic music plays over and over in an agonizing repetition, no one seems to flinch at how disturbing this has turned out to be. "Is it symbolic? IS IT SYMBOLIC?" queries Jerry Lawler. But no one knows how to address the question, and throws it to the WrestleMania Rage party from the night before ("Kids, I don't know what's worse: seeing that police officer-type man hanging, or Shane O'Mac pretending to be up in da club").