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WWE Hell in a Cell 2016: Most Shocking Hell in a Cell Moments of All Time

Erik BeastonOct 27, 2016

There was a time when Hell in a Cell was a match reserved only for the most intense rivalries, the final destination for wrestling's greatest feuds. Sunday night, Raw will present a pay-per-view sharing the name of the popular gimmick match, headlined by three separate main events, none with the sheer hatred that accompanied the contest in the past.

The likelihood that moments are created that help define the current era of the contest is high, particularly in the Women's Championship bout pitting Sasha Banks against Charlotte.

Yet there will still be those who point to the past and the moments delivered by Undertaker, Mankind, Shawn Michaels and Shane McMahon as the definition of what Hell in a Cell is at its core.

As the pay-per-view approaches and fans long for the days of violence that does not fall within the parameters of "PG," relive these six moments that rank as the most shocking in the match's long and unforgettable history.

6. A Chokeslam to Hell...or the Flatbed of a Pickup

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The main event of Armageddon 2000 saw the first-ever six-man Hell in a Cell bout for the WWE Championship. Kurt Angle, Steve Austin, Triple H, The Rock, The Undertaker and Rikishi battled for the top prize in the industry, but it was the latter two that created the most memorable moment of the night.

Battling atop the steel prison of pain, Undertaker grabbed Rikishi by the throat and proceeded to chokeslam him 30 feet to the bed of a pickup truck that had been driven to ringside at the order of Vince McMahon. It was the epic big bump fans had expected and one that left the audience erupting into cheers.

As The Phenom laid on his belly, his tongue out of his mouth as if he was a Satanic serpent from hell, he had yet again provided fans with the iconic moment they had come to expect from him inside wrestling's most dangerous gimmick bout.

5. The Beast Is Unleashed

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After two months of waging war over the WWE Championship, The Undertaker and Brock Lesnar settled their differences inside Hell in a Cell at No Mercy 2002.

The Beast Incarnate, then known as The Next Big Thing, was visibly shaken as he entered the structure and stood across the ring from his opponent. But by match's end, he would be the undisputed top star in the sport, his credibility confirmed in the most brutal of manners.

Lesnar was bloodied, for the first time his impenetrable dominance called into question by the determined and brutal challenger. But he managed to fight through the crimson mask to force a geyser of the red stuff from the forehead of his opponent and put him away with an F-5.

The WWE champion stood on top of the cell, his title raised high overhead, an announcement to even his harshest of critics that he was the new face of badassery in sports entertainment. 

4. Undertaker Hangs Big Boss Man

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One of the most horrific scenes ever witnessed in Hell in a Cell happened after one of the worst matches at WrestleMania XV.

The Undertaker had just defeated Big Boss Man in a slow, plodding, uneventful match when The Brood descended from the rafters of Philadelphia's First Union Center, a noose in hand.

From there, Edge, Christian and Gangrel proceeded to string Boss Man up and hang him from the ceiling of the cell as it raised to the heavens.

The imagery of Boss Man hanging, his body limp and lifeless, was haunting. Given the real tragedy that occurred just two months later, when Owen Hart tragically fell to his death, not to mention Boss Man's passing in 2004, it was an unnecessarily stupid booking decision born in the constant need for shock television that plagued parts of the Attitude Era.

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3. That's Gotta Be Kane!

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When The Undertaker battled Shawn Michaels in the inaugural Hell in a Cell match, fans bore witness to one of the greatest bouts in WWE history. A bloody grudge match that served as the culmination of a months-long feud, it was everything it was billed as and more.

Michaels took an epic ass-kicking, and Undertaker looked every bit the dominant force he had been for his entire career. Before he could finish off The Heartbreak Kid and cash his ticket to Survivor Series and a date with Bret Hart for the WWE Championship, though, the lights dimmed and a haunting organ sounded over the PA system.

Pyro exploded and a mysterious monster of a man stepped through the curtain, clad in red and flanked by Paul Bearer. "That's gotta be...that's gotta be Kane!" Vince McMahon exclaimed on commentary as the newcomer came toe-to-toe with his long-lost brother.

Kane attacked his brother and left him laying, setting Michaels up for the win and igniting one of the most epic storylines in company history.

2. A Leap of Faith

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There is a reason The Undertaker is synonymous with Hell in a Cell. He appears in every moment on this list, an indication of his importance to the history of the contest.

At WrestleMania 32, he came out of his annual semi-retirement to battle Shane McMahon in one of the night's most anticipated bouts, a war for control of WWE's future. A shocking return by the prodigal son had sparked interest in the latest chapter of the McMahon family melodrama while fans were left wondering why The Phenom would do the bidding of the hated Vince.

None of that mattered once the competitor set foot inside the cage.

After a slow, plodding contest that was entirely too long, fans got the moment they had waited for when Shane scaled the cell and jumped off. Undertaker, showing great timing and awareness, rolled out of the way and watched as his boss' son crashed through the announcers' table.

The wrestling world was in awe by McMahon's leap of faith, erasing the disappointment surrounding the rest of the match. 

1. "Good God, He Killed Him!"

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There are few moments more storied, haunting or horrifying than the June 1998 Hell in a Cell match between Undertaker and Mankind from King of the Ring.

After two years of waging war against each other, the Superstars came together for a match that should have wrapped their program up for good but instead linked them forever.

On that night, Mankind (Mick Foley) would ensure he would live in infamy as he soared off the top of the cell and through an announce table. He was chokeslammed through the roof of the steel structure and left knocked unconscious for the first time in his career.

A chokeslam onto a pile of thumbtacks, followed by a Tombstone, would end Foley's night on a losing note, but it was his willingness to sacrifice his well-being for the sake of the fans' entertainment, not to mention several iconic soundbites from commentator Jim Ross, that would leave the veteran competitor the biggest winner in the history of the gimmick contest.

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