The Undertaker and Mankind had one of the ugliest and most absorbing feuds the WWF produced in the late 1990s. Their rivalry ran from 1996 to 1998 and became one of the promotion’s defining dark stories of that period, which involved betrayal, escalating violence, and two characters who seemed to bring out something genuinely dangerous in each other.
The feud began on the April 1, 1996 episode of Raw, the same night Mankind made his WWF debut. After Mankind defeated Bob Holly earlier in the show, he returned later in the night to attack The Undertaker during his main event match. He was able to take full advantage of a tired Undertaker and eventually applied the Mandible Claw, leaving him unconscious.
The Undertaker was already one of the company’s biggest stars, with Paul Bearer at his side for years as his manager and closest ally. But Mankind came in as a very different kind of opponent. He was erratic and unsettling, willing to push The Undertaker into harsher and more chaotic situations than most of his earlier rivalries had required.
Over the following weeks, Mankind kept finding ways to disrupt The Undertaker’s world. On the May 13 episode of Raw, he locked The Undertaker inside a casket, beat on it with a pole until it was visibly dented, and pushed it over with him still trapped inside.
Later that month at In Your House 8, he cost The Undertaker the WWF Intercontinental Championship in a casket match against Goldust. When The Undertaker went to open the casket to finish the match, Mankind was already waiting inside. He grabbed The Undertaker, applied the Mandible Claw, and put him to sleep inside the casket, handing Goldust the win. Mankind was steadily chipping away at the aura and control that had defined The Deadman for years.
The first major singles match between the two came at King of the Ring on June 23, 1996. They brawled in and out of the ring before Bearer tried to help The Undertaker by passing him the urn, only for the attempt to go wrong and accidentally strike The Undertaker with it instead. Mankind locked in the Mandible Claw on the dazed Undertaker and won by submission.
It was a significant upset. And at this point, Mankind wasn’t just getting The Undertaker’s attention; he had now beaten him on a major pay-per-view and began stripping away pieces of the invincibility that had surrounded The Undertaker since his debut.
At SummerSlam on August 18, 1996, in Cleveland, the feud took its biggest turn. The two met in the first Boiler Room Brawl match, fighting through the boiler room and arena corridors for nearly 30 minutes, using ladders, pipes, and anything they could find before eventually making their way ringside, where the winner needed to claim Paul Bearer’s urn.
In a shocking ending, Paul Bearer turned on The Undertaker, hit him with the urn, and handed it to Mankind, giving him the victory. After nearly six years as The Undertaker’s manager, Bearer had chosen the other side. The Undertaker was now without his anchor, and his character began shifting toward a colder, more self-reliant persona that would define him for the rest of his career.
With Bearer now firmly in Mankind’s corner, The Undertaker pursued them both. Mankind challenged Shawn Michaels for the WWF Championship at In Your House: Mind Games on September 22, 1996, but lost after being disqualified when Vader attacked Michaels. After the match, Bearer opened the casket that had transported Mankind to the ring, only to find The Undertaker waiting inside. He came out and attacked Mankind, sending a clear message that the feud was far from finished.
The two then met in the first ever Buried Alive match at In Your House: Buried Alive on October 20, 1996. The Undertaker won by chokeslamming Mankind into an open grave and covering him with dirt, but Goldust, Hunter Hearst Helmsley, and Terry Gordy, working as The Executioner, dragged Mankind free and buried The Undertaker instead. The show closed with The Undertaker’s hand rising through the dirt, signaling he wasn’t done yet.
They met again at Survivor Series on November 17, 1996, in Madison Square Garden, with Paul Bearer suspended above the ring in a shark cage. The stipulation gave The Undertaker five minutes alone with his former manager if he won. Which he did by pinning Mankind after a Tombstone, but The Executioner ran in to help Bearer escape before the stipulation could be enforced.
The feud reached its next major match on April 20, 1997, at In Your House: Revenge of the Taker. The lead-up to the match had added fresh heat when Mankind threw a fireball into The Undertaker’s face on Raw, forcing him to enter the match with his eye bandaged. Bearer had also tried to reconcile with The Undertaker on the March 31 episode of Raw, and when The Undertaker refused, Mankind attacked from behind.
In the match itself, The Undertaker put Mankind through the announce table headfirst and finished him with a Tombstone to retain the WWF Championship. After the bell, The Undertaker turned his attention to Bearer and burned him with a fireball of his own, a moment that would eventually connect to the debut of Kane later that year.
By that point, the first chapter of the rivalry had run its full course, having moved from a debut-night attack through a manager’s betrayal and into the first Boiler Room Brawl and first Buried Alive match the WWF had ever produced.
The final chapter came in 1998. Mankind had cycled through other personas, but returned on the June 1 episode of Raw is War and interfered in a number one contender’s match between The Undertaker and Kane, applying the Mandible Claw and costing The Undertaker the victory.
On June 15, the two met again when The Undertaker and Stone Cold Steve Austin faced Kane and Mankind in a Hell in a Cell match on Raw that ended in a no-contest.
That set up a one-on-one Hell in a Cell match at King of the Ring on June 28, 1998, the famous match between the two that has been talked about ever since.
Before the match started, Mankind climbed to the top of the steel cage with a chair and waited for The Undertaker to enter. The Undertaker, working through a fractured ankle, climbed up after him. After exchanging punches and chairshots on top of the cell, The Undertaker grabbed Mankind and threw him off the top, sending him through the announcer’s table and onto the concrete floor below.
The cell was raised with The Undertaker still on top so a stretcher could be brought out, and Mankind was loaded onto it and wheeled toward the back. At this point, The Undertaker began climbing down, but then Mankind got off the stretcher, fought off the officials, and began climbing back up.
The Undertaker met him on top again, and after a brief exchange, The Undertaker chokeslammed him through a panel on top of the cell, sending him crashing to the mat inside the ring, where a chair followed him down and struck him in the face.
But even after all this, Mankind continued competing. Back on his feet, Mankind landed a piledriver onto the chair, then placed it over The Undertaker’s head and dropped a leg across it to stun him long enough to retrieve a bag of thumbtacks from under the ring.
He emptied them onto the mat, but The Undertaker reversed Mankind’s attempt to use them, slamming him back-first into the tacks, then chokeslamming him onto them, and finishing the match with a Tombstone.
Mankind’s refusal to stop through all of it earned him a standing ovation from the crowd, and his place in the company changed permanently after that night.
The feud worked because neither man was the same by the end of it. The Undertaker was pushed into new creative and physical territory, while Mankind went from an unsettling newcomer to one of the most beloved figures the promotion had ever produced.
It produced the first Boiler Room Brawl, the first Buried Alive match, and a Hell in a Cell that still defines the rivalry for most fans. It also helped establish that the WWF’s next chapter would be built on stories darker and more unpredictable than anything that had come before.
