On June 28, 1998, The Undertaker and Mankind entered The Igloo in Pittsburgh for the most iconic match of their careers.

The Hell in a Cell match, which was on the undercard of the King of the Ring pay-per-view, left fans in awe of the spectacle unfolding before them.

While the contest has been replayed to excess, there is no denying its place in WWE history as one of the most shocking and unforgettable contests in company history.

In the years since, WWE has produced countless other matches that have been classified as "extreme," with Superstars throwing caution to the wind and risking their well-being in pursuit of immortality and in the name of entertaining fans.

In celebration of 26 years since that epic encounter, these are the 25 most extreme matches in WWE history.

25. Boiler Room Brawl: Undertaker vs. Mankind (SummerSlam 1996)

The Undertaker and Mankind's feud reached a fever pitch in 1996, leading to a first-ever Boiler Room Brawl at that year's SummerSlam.

Starting in the namesake room and ending in the squared circle, it was a physically demanding contest that saw the competitors absorb tremendous punishment from weapons unlike any that had been utilized before and take bumps on surfaces most definitely not intended to be fallen on.

Upping the physicality to match the escalating hatred between the two, it was a brutal match that continued the trend of punishing battles between the hated rivals.

Mankind ultimately won the match when Paul Bearer shockingly betrayed The Deadman, ending a six-year relationship that had seen them rise to stardom together.

Not the only time a showdown between these two that will appear on this list, but it set the tone for the more famous encounter that followed and is a hidden gem in one of the greatest rivalries in WWE history.

24. Inferno Match: Undertaker vs. Kane (In Your House: Unforgiven 1998)

How wild was the Attitude Era in WWE?

The Undertaker and Kane had a match in which the only way to win was to light one's opponent on fire.

The bout itself was nothing special, undeniably limited by the fire surrounding the ring, but the spectacle was extraordinary.

With every big bump, the flames shot higher into the air. With every high spot, even more.

When Undertaker took flight, soaring over the flames, the legacy of the match was already secured. By the time he knocked Kane into the fire, setting him ablaze and securing the win, it was merely icing on the cake.

Was the match particularly good? Not by any stretch, and each one thereafter was progressively worse. But if there is one shining example of the extreme lengths WWE went to during its most audacious era, it's the Inferno match.

23. Elimination Chamber (Survivor Series 2002)

Triple H, Chris Jericho, Kane, Shawn Michaels, Booker T and Rob Van Dam entered the Elimination Chamber for the first time in November 2002 at Survivor Series and introduced the world to just how unforgiving the new steel structure could be.

Fashioned with steel chain and metal grating, the match was torture for the participants faced with the task of waging war inside of it. Bumps to the outside of the ring left the combatants with welts across their backs. The chains provided no relief when sent crashing into them, and the plexiglass pods threatened to cut any opponent who flew into them.

In the years since this match, the structure has been upgraded to better protect the participants. But that first bout did as much damage to the men competing for the World Heavyweight Championship as their opponents.

Triple H again proved his toughness, competing with a crushed trachea suffered early on following a Five Star Frog Splash from Van Dam, whose knee caught him in the throat in the process.

The Game managed to complete the match while barely being able to breathe, completing one of the most awe-inspiring performances of his career.

In hindsight, it is almost a miracle that the Elimination Chamber was brought back.

22. Hell in a Cell: Cactus Jack vs. Triple H (No Way Out 2000)

One month after an excellent Street Fight captivated fans at the 2000 Royal Rumble, Triple H and Cactus Jack rekindled their rivalry in a Hell in a Cell match.

Adding higher stakes was the stipulation that if Jack lost, his career would be over. Mick Foley, the man behind the Wanted: Dead or Alive shirt would hang up his boots and never again challenge for the WWE Championship.

While that did not hold up, the match sure does.

Building on spots and moments from their previous encounter, the contest featured Jack again dragging out a sadistic side out of Triple H. He even answered it, utilizing a barbed wire two-by-four and threatening to blast the heel champion with a flaming version of the same weapon.

However, The Game back-dropped Jack through the roof of the cell, sending him crashing to the mat below. From there, the outcome was academic.

A perfect follow-up to the instant classic from a month earlier, the battle inside the cell felt more like controlled chaos compared to the unabashed violence of their first encounter, accounting for its spot further down the card than that original outing.

21. Last Man Standing Match: Chris Jericho vs. Triple H (Fully Loaded 2000)

Triple H was on another level from every other in-ring performer as the Millennium arrived, and the proof is in the many instant classics he turned in over the course of 2000.

Case in point, a rage-filled Last Man Standing match against Chris Jericho at the Fully Loaded pay-per-view.

The culmination of a rivalry that started when Jericho repeatedly poked fun at and verbally insulted Stephanie McMahon-Helmsley, it escalated, with The Game brutalizing and bloodying Y2J shortly before the match.

A physical battle, it featured Triple H dominating his opponent and allowing his hubris to get the better of him. He kicked his feet up, laying across the top rope in between beating Jericho down, as if to suggest it was a piece of cake.

That confidence was used against him late, when a bloodied Jericho fought back, busting Triple H open and appearing close to victory. Instead, The Game drove him through a table and barely made it back to his feet by the count of 10.

The match proved Jericho could run with the best in a legitimate main event setting while further cementing Triple H as the measuring stick that year. It also established The Cerebral Assassin as one of the best main event brawlers.

It would be a trait he would embrace and use to his advantage for the remainder of his career.

20. 'I Quit' Match: John Cena vs. JBL (Judgment Day 2005)

The "I Quit" match at Judgment Day 2005 was a huge test for John Cena as WWE champion.

His victory over JBL at WrestleMania 21 did not necessarily live up to the hype and, despite having a rap record released and the full support of WWE behind him, Cena needed a performance that served as an emphatic statement that he belonged in that position.

He delivered. Big time.

Cena proved he could take an ass-kicking. He wore the crimson mask, sold everything for JBL and gave fans their first hint of the come-from-behind formula that would become a defining trait of his matches.

With his face caked in blood, he raised an exhaust pipe from the tractor trailer he rode in on overhead and threatened to hit JBL with it. That was all the brash, loudmouthed New Yorker needed to quit.

A classic match that feels somewhat forgotten nearly two decades later, it was a pivotal moment for Cena and one that proved he had what it took to be the top guy for an industry desperately seeking its star of the future.

19. End of an Era: Triple H vs. Undertaker (WrestleMania 28)

The Hell in a Cell match between Triple H and The Undertaker at WrestleMania 28 occurred in the heart of WWE's PG Era, meaning the competitors could not resort to the same violence or use of blood that they had in previous encounters a generation earlier.

But that did not stop them from delivering a punishing encounter featuring some of the best storytelling in recent memory.

Building on spots from their previous matchups, they weaved their narrative in and out of spots including steel chairs and ring steps, all while beating the life out of each other.

They each fought for a distinct purpose.

For Triple H, it was all about ending The Deadman's unbeaten streak at WrestleMania and avenging his friend Shawn Michaels, who was retired by The Undertaker following a loss two years earlier.

For The Deadman, it was about defending a streak he had worked two decades to build.

Add in the drama of Michaels as guest referee, and it was as much about extreme storytelling as it was the actual action unfolding before the fans.

Ultimately, Undertaker earned the win with a devastating Tombstone but both men limped away from the squared circle as they said goodbye to an era.

18. 6-Pack Hell in a Cell Match for WWE Championship (Armageddon 2000)

Six of the top Superstars in WWE set foot inside Hell in a Cell in December 2000, with the top prize in the industry at stake in the main event of Armageddon.

Kurt Angle defended the WWE Championship against The Undertaker, The Rock, Steve Austin, Triple H and Rikishi in a star-studded affair that would continue the legacy of Hell in a Cell as one of the most brutal match types in the industry.

All six men were busted open, their bodies tormented by the unforgiving walls of the steel structure.

It would be Rikishi who endured the worst of it, though, as he and Undertaker fought to the top of the cage, only for The Deadman to guzzle him and send the super heavyweight crashing onto the bed of a conveniently placed pickup truck below.

Angle retained the title, but it was his first real test in a big-time gimmick match that required him to introduce a gritty, brawling style to his arsenal.

17. Hell in a Cell: Batista vs. Triple H (Vengeance 2005)

World heavyweight champion Batista and Triple H wrapped up their epic rivalry in June 2005 at the Vengeance pay-per-view inside Hell in a Cell.

Faced with the task of keeping fresh a match that had seen just about every major stunt possible, the brawlers sacrificed the high spot for brutality, delivering a hard-hitting match that was appropriately weapon-filled and bloody.

Despite one last attempt by The Game to utilize his trusty sledgehammer to his benefit, Batista instead delivered a Batista Bomb onto the ring steps, resulting in a thud and a referee's three-count.

The performers flipped the Hell in a Cell match, taking a bout typically associated with some big bump off the top or side of the cage and making it the setting for one last war of attrition with the top prize on the Raw brand at stake.

A beautifully brutal match that would have been right at home in 1980s Jim Crockett Promotions.

16. Tag Team Ladder Match: Edge and Christian vs. The New Brood (No Mercy 1999)

At No Mercy in October 1999, The New Brood's Matt and Jeff Hardy and the team of Edge and Christian waged war in a tag team ladder match in the finals of the Terri Invitational Tournament, with the managerial services of Terri Runnels and $100,000 at stake.

While most believed the two teams would shine given the quality of their work to that point, no one could have imagined the risks they would take to steal the show and just how much the instant classic would impact the future of the industry.

The four performers threw caution to the wind, creating unfathomable spots and wowing the fans in Cleveland.

The teeter-totter spot by Jeff remains one of the shinning moments from the match, but the brutality of bodies hitting ladders kept fans engaged and the sense of urgency with which the wrestlers competed told the story of four young stars seizing the moment and making it their own.

The Hardy brothers would ultimately win the match, but it was nearly impossible not to recognize the incredible efforts of all four men and how much they put into what was previously a throwaway match on the star-studded card.

It also laid the groundwork for some of the matches further up this list.

More on them in a bit.

15. Hardy Boyz vs. Dudley Boyz vs. Edge and Christian (WrestleMania 2000)

Before there were tables, ladders and chairs, The Dudley Boyz, Hardy Boyz and Edge and Christian waged war in a Triangle ladder match at WrestleMania 2000.

The bout built on two prior meetings: the tag team ladder match between the Hardys and Edge and Christian at No Mercy the previous May and the tables match between the Dudleys and Hardys two months earlier.

High spots, big bumps and a jaw-dropping finish that saw Matt Hardy shoved off a table bridging two ladders and through tables below defined a contest that was another important step in establishing the three teams as the faces of a new era.

Edge and Christian won the bout, but all three would see their stars rise significantly as a result of their performance in the matchup.

And, par for the course, WWE officials would find new ways to introduce extreme to a product begging for it.

14. Hell in a Cell: Undertaker vs. Brock Lesnar (No Mercy 2002)

The rivalry between Brock Lesnar and Undertaker escalated beyond that of a championship program and involved lies about infidelity on The American Badass' part.

Fueled by vengeance, The Deadman took to the confines of Hell in a Cell, a structure he was all too familiar with, and looked to put an abrupt end to The Beast Incarnate's WWE Championship reign.

Instead, he found out just how dangerous Lesnar could be.

Undertaker had his broken hand brutalized by the concentrated attack of The Beast. He got his licks in on the former NCAA wrestling champion, too, busting the heel open, but it never felt like the title was in jeopardy.

Lesnar thrived in those conditions and despite reeling a time or two, ultimately countered a Tombstone attempt into an F-5 and scoring the pinfall victory in what proved to be a defining match in his still-young career.

With even Paul Heyman bleeding at cageside, it was a match befitting the stipulation and one that continued to carry on the legacy of the cell as a breeding ground for extreme classics.

13. Submission Match: 'Stone Cold' Steve Austin vs. Bret Hart (WrestleMania 13)

Professional wrestling history was forever changed when "Stone Cold" Steve Austin and Bret
Hart clashed in a submission match as one of the co-main events of WrestleMania 13.

A wild, chaotic brawl that saw the combatants unleash months of frustration on each other, it also featured the star-making performance from The Texas Rattlesnake, who bled buckets but refused to give up.

Trapped in the Sharpshooter and screaming in agony, Austin fought through the pain until his body could no longer take it, causing him to pass out and special referee Ken Shamrock to call for the bell.

A match that was appropriately brutal given the intensity of the rivalry between Hart and Austin, with a referee perfectly suited to handle the situation if either competitor got out of hand, it was a perfect match and one of the most important in pro wrestling history.

Austin and Hart expertly executed a double-turn, with Stone Cold becoming the rebellious antihero and The Hitman becoming the whiny bad guy who could not come to grasps with the changing landscape in the United States.

An all-timer of a match and a brawl that earns its place among the most extreme.

12. TLC I: Hardy Boyz vs. Dudley Boyz vs. Edge and Christian (SummerSlam 2000)

On the heels of a triangle ladder match at WrestleMania 2000 that introduced tables and chairs to the fray, commissoner Mick Foley booked cowardly champions Edge and Christian to defend their titles against The Dudley Boyz and Hardy Boyz in the first-ever Tables, Ladders and Chairs match.

As one might expect, chaos ensued.

There were bone-rattling chair shots, big table bumps and high-risk dives from ladders. One spot saw D'Von Dudley, terrified of heights in real life, dangling from the contraption holding the tag team titles along with Jeff Hardy, while his partner, Bubba Ray, took a swan dive off a massive ladder and through an array of tables positioned at ringside.

Edge and Christian retained their titles, but not necessarily because they won the match. It was as if they survived, just narrowly escaping with the gold despite their bodies feeling as if they had been in a car accident.

The match set a bar seemingly impossible to eclipse but, luckily for the competitors and the fans eager for the sequel, impossible was not a word any of the six men involved comprehended.

11. 'I Quit' Match: Mankind vs. The Rock (Royal Rumble 1999)

The "I Quit" match between Mankind and The Rock was immortalized in the 2000 major motion picture, Beyond the Mat, a documentary that took fans inside the world of professional wrestling.

The match, essential in the evolution of The Great One, saw him brutalize the beloved masked babyface, culminating in him handcuffing Mankind and bashing him in the face and head with a dozen steel chair shots.

Like the more infamous Hell in a Cell, it crossed the line from extreme fun to discomfort as there was no adequate way for Mankind to protect himself as Rock relentlessly swung the chair and made contact.

It fit the story, especially with the babyface telling his rival he would never utter the words "I quit," no matter how much pain and suffering he was put through. The Corporation's chosen one answered by knocking him unconscious and airing an audio clip of him saying it instead, earning a tainted win and continuing their rivalry.

One of the shining examples of the brawl-heavy, weapons-filled Attitude Era main events, it is a match that is key to the growth of one of the industry's giants.

10. Hell in a Cell: Undertaker vs. Shawn Michaels (In Your House: Badd Blood)

Before he made Mankind famous, Undertaker punished Shawn Michaels in the inaugural Hell in a Cell, brutalizing The Heartbreak Kid in the culmination of a months-long rivalry.

With nowhere to go, Michaels absorbed the focused attack of his opponent, punishing him with hard rights and lefts and throwing him around the steel structure with reckless abandon. He obliterated Michaels and appeared to be on track for a blowout win when his long-lost brother, Kane, emerged from the darkness and came face-to-face with his older sibling.

After Kane's shocking Tombstone to The Phenom, a bloodied Michaels inched his way to his opponent, draped his arm over him, and scored the tainted victory.

The match was a masterpiece of storytelling and brutality, mixing extreme action with a narrative that was easily followed. Michaels relied on his friends, Triple H and Chyna, to help him. Without them, he endured a beating and only won when he had interference from and outside force of nature.

It was a great match, a fittingly brutal display, with a great finish that put over Michaels as a classic cheap heel.

9. Tommy Dreamer and The Sandman vs. The Dudley Boyz (ECW One Night Stand 2005)

The inaugural ECW One Night Stand PPV was the most organically ECW thing that WWE has done with the product. It was pitched as one last goodbye to a brand that meant so much to the fans and the wrestlers.

In June 2005, the show delivered on the extreme nostalgia that fans demanded, including a main event tag team match that was equal parts hard-hitting, plunder-filled and bloody.

The Dudley Boyz teamed up to defeat Tommy Dreamer and The Sandman in a match that featured run-ins from several stars, a staple of ECW party matches and was capped off with a flaming table spot that saw Dreamer powerbombed through it.

The match, featuring four of the most important and influential stars in that company's history, delivered everything fans wanted and put the perfect exclamation point on a show that had even the most hard-skinned members of that roster emotional by night's end.

8. Hardcore Match: Cactus Jack vs. Randy Orton (Backlash 2004)

For months, Randy Orton disrespected and assaulted Mick Foley. Embracing his "Legend Killer" persona, he went as far as to spit in the face of the Hardcore Legend and even kicked him down a flight of stairs.

He would get his comeuppance at Backlash in April 2004, at the hands of Foley's most dangerous alter egos.

Cactus Jack returned for the Hardcore match for Orton's Intercontinental Championship and wasted little time introducing his preferred weapons into the fray. The third-generation heel answered, pulling a bag of thumbtacks from under the ring in hopes of utilizing them to his advantage.

Instead, The Viper found himself tossed into the jagged tacks.

Despite being in shock, Orton continued the battle, absorbing everything Jack threw at him before catching him with a well-timed RKO for the victory.

The match did for Orton what Foley's battles with The Rock had done for him in that it proved to the WWE Universe that the young star could be ruthless and violent when needed.

He dragged those qualities out of Cowboy Bob Orton's son and ensured he would have every necessary asset to be a top-tier star of the next generation.

7. Hardcore Match: Mick Foley vs. Edge (WrestleMania 22)

Mick Foley again found himself faced with the task of elevating a potential main event star, this time in a Hardcore match at WrestleMania 22.

Not only was it a career-defining opportunity for Edge, but it was equally as significant for Foley, who had yet to have a legitimate 'Mania moment as he walked to the ring in Chicago on April 2, 2006.

That would change as The Hardcore Legend and The Rated-R Superstar delivered a near-perfect match.

Edge speared Foley, only for the babyface to reveal he had wrapped his midsection in barbed wire and therefore damaging his opponent's arm. Foley sent his cocky opponent into a bed of thumbtacks and even applied a Mr. Socko and barbed wire-assisted Mandible Claw to Lita.

It was the match-concluding spot, though, that lives in immortality.

Edge raced across the ring and speared Foley through the ropes and into a flaming table before crashing to the ground below. Three seconds later, he secured the most important victory of his career and Foley had that elusive WrestleMania moment.

And the event itself added another extreme moment to its annals.

6. WWE Championship Match: Eddie Guerrero vs. JBL (Judgment Day 2004)

The match between Eddie Guerrero and John Bradshaw Layfield at the 2004 Judgment Day PPV remains one of the bloodiest battles in WWE history.

A chair shot by Layfield opened Guerrero up, instantly giving the champion a crimson mask.

The babyface became even more sympathetic to the Los Angeles crowd than he otherwise may have been, bleeding buckets as he absorbed punishment at the hands of his bigger, stronger opponent.

He appeared to be slowed by the blood loss at one point and crumbled to the mat at another, but he mustered enough energy to blast JBL with the WWE title, drawing the disqualification finish and ensuring the feud would continue.

So caked in plasma is the match that the event itself is rated "TV-MA" on both the WWE Network and Peacock.

5. Terry Funk, Tommy Dreamer and Beulah vs. Edge, Mick Foley and Lita (ECW ONS 2006)

In the sequel to ECW One Night Stand 2005, WWE produced a show it had hoped would create buzz and excitement for the relaunched brand.

One of the marquee bouts on the card pitted Tommy Dreamer, Terry Funk and Beulah against Edge, Lita and a newly heel Mick Foley.

The match saw Foley and Funk deliver their brand of hardcore violence, the likes of which saw them punished with barbed wire, two-by-fours and even fire.

Edge and Dreamer formed the foundation of the match, and Lita and Beulah added the catfight element to the contest.

Ultimately, Edge speared Beulah, folding her in half to pin her as he added insult to injury.

The match was better than the tag team main event from the year before and may be one of the hidden gems of the 2000s in WWE.

Appropriately violent as Foley denounced the hardcore way, only to be dragged back into it by his friend and mentor Funk, it was a great watch and one that further established The Rated-R Superstar as a main event entity in the company.

4. Street Fight: Cactus Jack vs. Triple H (Royal Rumble 2000)

Triple H has gone on record and referred to his Royal Rumble 2000 Street Fight against Cactus Jack as the match that solidified his spot as a main event star.

He's not wrong.

The Game had been positioned at the top of the card for months prior to the showdown but had not truly cemented his place as one of the guys in the company. That changed with a brutal, violent war with Jack, which was the culmination of an intensely personal rivalry.

For weeks, Triple H and the McMahon-Helmsley regime had toyed with Foley and his family, going as far as to fire him and then mock him on a weekly basis.

That changed when Foley returned and reintroduced the wrestling world to his most extreme persona.

Inside Madison Square Garden, Jack brutalized The Game, testing his toughness and daring him to match his sadism. The WWE champion did so, despite a nasty gash on his calf.

Much like The Rock had a year earlier, he handcuffed Jack and teased unloading a barrage of chair shots, only to have The Great One get involved and save his tag team partner.

Late in the match, it looked like a new champion may be in order, but Triple H recovered and delivered a Pedigree into a pile of thumbtacks to retain his title.

A match as great in overall quality as it is in unabashed violence, it was a tone-setter for WWE's extraordinary 2000 and another reminder of how significant Foley was to the careers of more than one budding main event star.

3. Street Fight: Shane McMahon vs. Kurt Angle (King of the Ring 2001)

The 2001 King of the Ring Street Fight between Kurt Angle and Shane McMahon took the wrestling world by storm, devolving into the sort of violence no one could have anticipated and leaving both men licking their wounds.

Angle, wrestling his third match of the night, suffered a broken tailbone as he delivered a suplex to McMahon on the floor. From there, he proceeded to throw McMahon into the glass set, which did not break. He did it again but still not shattering it.

He eventually broke two of the panes, McMahon bleeding profusely as the fight returned to the ring.

The combatants took fans on a roller-coaster ride through the final moments before Angle launched himself and his opponent off the top rope with an Olympic Slam to put an end to the match and secure the victory.

To that point, Angle had been a technically sound wrestler but had not proved he could be a gritty brawler. That ended on that June night in 2001, with a classic match against a most unlikely opponent.

The involvement of glass and the manner in which both competitors were legitimately hurt elevates the match up this list and into the top three.

2. TLC II: Hardy Boyz vs. Dudley Boyz vs. Edge and Christian (WrestleMania X-Seven)

Faced with the unenviable task of building on a classic TLC match from the previous SummerSlam, The Hardy Boyz, Dudley Boyz and Edge and Christian ran it back on the grandest stage in professional wrestling,

Building on spots from their previous encounter, the contest upped the risk and violence, with death-defying spots from Matt and Jeff Hardy, calculated damage from Edge and Christian, and fist-throwing from Bubba Ray and D'Von.

The classic spot from the match saw Jeff dangling from the belts high over the ring, only for Edge to leap off a ladder and deliver a Spear that took both crashing to the mat below.

Interference from Rhyno, Spike Dudley and Lita ramped up the extreme action, including a chair shot from the latter to the runt of the Dudley clan that just sounded like it hurt, en route to Edge and Christian somehow managing to escape another TLC match with the tag titles.

Even better than the original, with more death-defying spots and jaw-dropping moments, it is the Godfather II of pro wrestling sequels.

1. Hell in a Cell: Undertaker vs. Mankind (King of the Ring 1998)

At some point in the epic King of the Ring 1998 encounter, the Hell in a Cell match between Undertaker and Mankind transitioned from extreme to extremely uncomfortable to watch.

Perhaps it was around the time that The Deadman flung Mankind off the top of the structure, sending him crashing through the announce table below with no protection from the blow.

Maybe, it was after Mankind climbed back up to the top of the cage, his shoulder clearly damaged, for more punishment. If not, then definitely when The Phenom chokeslammed him through the ceiling of the structure and watched him crash to the mat below.

Assuming you made it that far, maybe it was the tooth stuck in Mankind's beard.

Whatever the case, and knowing the damage that match did to the body of Foley, it is impossible not to watch the iconic Hell in a Cell match even 26 years later and not cringe at some point in its 17:38 run time.

A contest that reached "extreme" status even in comparison to what the stars of ECW were doing in Philadelphia, not to mention what would follow in WWE, it remains a shining example of demonstrating the escalation of a feud but also what should be considered too far for the safety of the stars involved.

Still, Undertaker and Mankind will be forever linked because of the utter chaos they caused that June night in Pittsburgh.