Ranking the 15 Matches That Defined WWE's Attitude Era

Erik Beaston@@ErikBeastonFeatured ColumnistApril 28, 2020

Ranking the 15 Matches That Defined WWE's Attitude Era

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    Credit: WWE.com

    The Attitude Era may be home to some of the most unforgettable moments in WWE history, but it was also the breeding ground for incredibly compelling, wholly unique matches that stand the test of time and help define that period for the company.

    Some were born of lengthy stories, such as Undertaker vs. Kane and Steve Austin vs. Mr. McMahon, while others were pure spectacle, such as Shane vs. Vince McMahon and the Tables, Ladders & Chairs matches that made stars of The Hardy Boyz, Edge and Christian, and The Dudley Boyz.

    The matches, ranging from Mr. McMahon's December 1997 introduction of the era to his June 2002 demand for ruthless aggression, have become staples of fans' top 10 lists and are ranked according to the historical significance to both the era and its top stars. In the event of a tie, how well the match reflects that period in WWE history was taken into consideration.

    As Bleacher Report continues its ode to the most popular, wild, chaotic, star-studded era in WWE history, relive these 15 matches that thrilled, shocked, wowed and compelled fans en route to earning their place in the annals of sports entertainment.

15. Undertaker vs. Kane (WrestleMania XIV)

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    A yearlong story of epic proportions, centered around the fire that killed The Undertaker's parents but spared his younger brother, Kane, accompanied one of the most anticipated matches on the WrestleMania XIV card.

    An intensely personal battle that followed The Big Red Machine's newsworthy Tombstone piledriver to baseball legend Pete Rose, it featured hard-hitting and dramatic near-falls. A vengeful Kane attempted to become the first Superstar to put a blemish on his brother's undefeated WrestleMania record, but no amount of punishment proved effective.

    After three Tombstones of his own, Undertaker vanquished the challenge of his younger sibling and put an end to their rivalry.

    At least for 24 hours, that is. Their feud, which ran off and on for the better part of a decade, ranks among the greatest in Attitude Era history, while their initial encounter is a reminder of how significant storytelling was to the highest-profile bouts during that period.

14. Good Housekeeping Match: Chyna vs. Jeff Jarrett (No Mercy 1999)

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    After nearly defeating him to capture the Intercontinental Championship a month earlier, Chyna rolled into the October 1999 No Mercy pay-per-view ready to shut up the male chauvinist Jeff Jarrett and etch her name in the history books.

    To do so, she would have to win the first-ever Good Housekeeping match, which played up Jarrett's claims that women belonged at home.

    Featuring spots and gimmickry usually reserved for the company's hardcore division, the performers creatively utilized household items to punish one another. A false finish saw Jarrett apparently retain his title via belt shot, only for the official to restart the match as a championship is not a common household item.

    A guitar is—according to, um, logic—and Chyna utilized it to pick up the win.

    She became the first woman to capture the Intercontinental Championship, a stat that should land her in the Hall of Fame above all else.

    The title change was representative of the risks the creative team was willing to take during the Attitude Era. Vince Russo and those who followed turned convention on its ear and went in directions never before explored.

    Chyna was over, she had shown an ability to work with her male peers and the fans bought her in that role. It was a risk worth taking and one that paid off, as she won the gold for a second time not even a year later.

13. Steve Austin vs. Dude Love (Over the Edge 1998)

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    Credit: WWE.com

    The arena brawl became a major element of all Attitude Era main events and was really perfected in the Over the Edge 1998 bout between WWE champion "Stone Cold" Steve Austin and Dude Love.

    As if the fight spilling to the entrance stage, a massive bump by Austin off it and to the arena floor, and the proverbial crimson mask for the champion weren't enough, storyline elements involving evil billionaire owner-turned-guest referee Mr. McMahon and special ring announcer Pat Patterson added to the drama.

    Their attempts to screw Austin out of the title added incredible heat to the match, while special enforcer The Undertaker's chokeslam of Patterson through the announce table late evened the odds.

    By the time an errant steel chair from Love knocked out McMahon, Austin dropped his challenger with a Stunner and Vinnie Mac's hand was used to count the fall, fans realized they had witnessed a classic main event.

    To this day, it remains one of the more underrated title bouts in company history, regardless of era.

12. Ladder Match: Triple H vs. The Rock (SummerSlam 1998)

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    The majority of the build leading into SummerSlam 1998 may have centered on Steve Austin and The Undertaker's WWE Championship match, but by show's end, the contest that had the fans buzzing was the ladder match for the Intercontinental Championship between D-Generation X's Triple H and The Nation's The Rock.

    The culmination of a monthslong feud between the faction leaders, it was as much about proving the participants' worth as main event stars as it was crowning the champion.

    In front of a red-hot audience at Madison Square Garden, Triple H and The Rock delivered a dramatic, hard-hitting, surprisingly brutal match that centered on The Great One's targeting of his opponent's injured knee and late interference from Mark Henry and Chyna.

    In the end, The Game withstood the pain in his lower extremities and near-blinding powder to the eyes to pick up the win and another IC title reign.

    It was The Rock, though, who emerged the real victor. Over 20,000 fans in the world's most famous arena chanted his name as he limped to the locker room, his face bloodied and his body battered. He would be the WWE champion within three months, which was no surprise to those who saw this performance.

11. Evening Gown Match: Sable vs. Luna Vachon (Unforgiven 1998)

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    Credit: WWE.com

    While Chyna, Lita and Trish Stratus would later be given the opportunity to display their in-ring abilities on a regular basis, Sable was the first woman to break out and become a major star for the company.

    Her rivalry with Luna Vachon early in 1998 elevated her star and ignited a fire within Sable that saw her become more aggressive and no-nonsense. It was during that program that she became incredibly popular, equaling ovations typically reserved for the likes of Steve Austin and The Rock during the era.

    At April's Unforgiven pay-per-view, the rivals settled their differences in the first-ever Evening Gown match in which the winner was the first woman to strip her opponent to her lingerie. The match was rather nondescript, relying on hair-pulling and strikes until a distraction by Marc Mero allowed Luna to rip off Sable's gown and earn the victory.

    The match (and every similar one thereafter) objectified women. It relegated them to be seen as mere eye candy, and only in the last few years has WWE started to address the imbalance between its presentation of male and female Superstars.

    At the time, during an era in which storylines and angles often flirted with the fine line between entertainment and bad taste, the contest laid the groundwork for a gimmick match that became a staple of WWE programming.

    Even as there is, rightfully, no place for it in today's landscape.

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

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    The Attitude Era afforded fresh, young talent the opportunity to seize opportunities and become bigger stars than they ever imagined. Case in point: Edge, Christian and The Hardy Boyz, who battled at No Mercy 1999 in the first-ever tag team ladder match in WWE history.

    The culmination of the Terri Invitational Tournament for the managerial services of Terri Runnels, the match would lay the foundation for every one of the multi-man ladder matches that would follow.

    The historical significance of it all was impressive, but even more so was the originality the four performers demonstrated. Edge, Christian, Matt and Jeff Hardy had nothing to work off. Two teams had never before been booked in the match type, so they were tasked with setting the example.

    They worked from the ground up, creating mesmerizing, awe-inspiring and death-defying high spots that kept the fans in Cleveland on the edge of their seats.

    "Oohs" and "aahs" permeated the historic Gund Arena as the combatants soared through the air, hoping their last burst of offense would be enough to win them the match.

    Ultimately, the Hardys earned the win, but all four participants received a standing ovation from a fanbase completely in awe of what it had just witnessed. Two teams facing the unenviable task of evolving a popular gimmick match accomplished what they set out to do, and they were greeted with appreciation.

    So much so that the ovation would bleed over to the following night's Raw.

9. Icon vs. Icon: The Rock vs. Hulk Hogan (WrestleMania X8)

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    By WrestleMania X8 on March 17, 2002, The Rock had become a massive crossover star the likes of which WWE had not seen before. He was about to be the star of a blockbuster film (The Scorpion King), and with movie offers pouring in, he appeared to be nearing the end of his days as a full-time in-ring performer.

    Sensing that his opportunity to maximize Rock's box-office potential in the world of professional wrestling on a regular basis was coming to a close, Vince McMahon brought in the New World Order for one last big payday.

    In a battle of legitimate industry icons, The Great One would battle "Hollywood" Hulk Hogan, the biggest and most recognizable star of wrestling's last big boom period.

    The dream match, in front of 68,237 fans in the historic SkyDome in Toronto, had the industry buzzing. More importantly, it demonstrated the desire for nostalgia in the industry, as Hogan generated a louder ovation than his opponent, whom the fans greeted with a chorus of boos.

    The back-and-forth encounter, a masterpiece of crowd manipulation, was light on technical wrestling but kept fans enthralled with a series of spots, near-falls and the classic signature offense of each competitor.

    The Rock scored the win, but in the end, Hogan emerged the real victor. After his run with WCW ended under less-than-stellar circumstances, he returned to the company that made him a star. Fans who grew up following the demands of Hulkamania greeted him as a conquering hero.

    Hogan would ride the wave of momentum to an unlikely WWE Championship run, while The Rock would become, you know, the biggest box-office star in film and entertainment over the decade that followed.

8. Street Fight for the WWE Title: Cactus Jack vs. Triple H (Royal Rumble 2000)

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    With Undertaker and Steve Austin sidelined because of injury, WWE officials finally took a chance on Triple H, elevating him to the top of the card as the lead villain. Though he won the WWE Championship and competed in high-profile main events against the likes of Austin, The Rock and even Mr. McMahon, he lacked that star-making performance that announced to the world he belonged in that spot.

    Then came the Street Fight for the WWE Championship against Cactus Jack at the 2000 Royal Rumble.

    After awakening a fire in Mick Foley by threatening his livelihood, mocking him and bad-mouthing his family, Triple H found himself faced with an unrelenting force in Jack, the most violent of The Hardcore Legend's personalities. The Game was pummeled around Madison Square Garden and endured a nasty laceration on his left leg. He managed to steal the upper hand by handcuffing Jack and blasting him with a barrage of chair shots to the head, only for The Rock to interfere and level him with a chair shot of his own.

    Barbed-wire two-by-fours and thumbtacks ultimately made their way into the match, with Triple H driving Jack face-first into the latter with a sickening Pedigree.

    The champion survived the match, emerging with his title, but more importantly earned the respect of the fans. He was a made man, something he could attribute to not only his own tireless efforts but also the creativity of Foley and the hell they put each other through on one of WWE's grandest stages.

    Without that match and his ability to rise to the level of Foley in that setting, who knows if Triple H would have ever been accepted as a genuine main event attraction.

7. Iron Man Match for the WWE Title: The Rock vs. Triple H (Judgment Day 2000)

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    At SummerSlam 1998, Triple H and The Rock squared off in a ladder match that stole the show and elevated their stars. By May 2000, the Superstars were at the peak of sports entertainment, the most prominent wrestlers in WWE feuding over the top prize in the industry. Their chemistry between the ropes impressed management enough that they were booked in an Iron Man match at the Judgment Day pay-per-view.

    For the first time since WrestleMania XII, two Superstars were trusted to keep the fans' attention for 60 minutes. Failure to do so would render an entire third of the event a disaster. Luckily for WWE, it had chosen one of the greatest in-ring technicians of his generation and the most charismatic performer since Hulk Hogan.

    In one hour, Rock and Triple H showed the entire world their growth as performers and proved why they were elevated to this level. They meshed traditional in-ring work with Attitude Era brawling and sprinkled in some quality sports entertainment in the form of special referee Shawn Michaels, interference from DX and the McMahons, and the return of The Undertaker after eight months away.

    Triple H won in controversial fashion, scoring the final fall via disqualification when Michaels caught Undertaker striking The Game, but there were no real losers. Everyone involved put together a phenomenal match that exceeded expectations and further established The Rock and Triple H as defining Superstars of the era.

6. WWE Championship Match: Mankind vs. The Rock (Raw, 1/4/99)

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    The January 4, 1999, episode of Raw was a pretaped show from Worcester, Massachusetts, that probably should have lost handily to WCW's live Monday Nitro broadcast. Yeah, it had a WWE Championship match between Mankind and The Rock slated for the main event, but WCW had Kevin Nash vs. Hulk Hogan and a huge audience at the Georgia Dome. What could possibly have gone wrong for Ted Turner's company?

    Hubris, that's what. Most notably, the arrogance of Eric Bischoff, whose previous attempts at spoiling WWE's results were well-documented. On that night, through commentator Tony Schiavone, he revealed a massive match outcome to his audience: Mick Foley would win the WWE Championship, defeating The Rock. Schiavone added, "Ugh, that'll put a lot of butts in the seats."

    Seats, no; but it did cause 600,000 viewers to simultaneously abandon the stale WCW product and jump ship to the USA Network, where they watched one of the most beloved performers of his (or any) generation realize his boyhood dream and capture the top prize in professional wrestling.

    Not only did the match feature the culmination of Foley's lifelong journey and one of the loudest pops The Rock ever garnered, but it also spelled the end of the Monday Night War as it had been. WWE would take a commanding lead in the battle for wrestling supremacy and never look back.

    All on the shoulders of Mrs. Foley's baby boy, whom fans felt compelled to share the moment with.

5. Street Fight: Shane McMahon vs. Vince McMahon (WrestleMania X-Seven)

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    In late 2000, Vince McMahon demanded a divorce from wife Linda, sending her into a catatonic state. He then proceeded to enter a torrid affair with Trish Stratus that enraged daughter Stephanie. Enter son Shane, who took exception to his sister and father's treatment of his mother and set up a Street Fight for WrestleMania X-Seven against his father.

    Throw in Shane's purchase of WCW just six days before their encounter, and the result was an emotional powder keg ready to explode.

    Explode it did, on wrestling's grandest stage.

    A jaw-dropping elbow from the top rope by Shane missed, sending him crashing through the announce table. As Vince seized control, Stratus made her way to the ringside area with a despondent Linda in a wheelchair. After weeks of humiliation, the future Hall of Famer slapped Stephanie and engaged her in a fight that spilled up the ramp and to the back.

    Vince continued dominating his son until Linda rose from her wheelchair, not quite as catatonic as her estranged husband thought, and delivered a low blow. Coast-to-Coast from Shane followed, and the prodigal son left The Show of Shows with one arm raised in victory by special referee Mick Foley, the other embracing his mother in a hug.

    The match was everything good about pro wrestling. It was physical, often over-the-top, but brought all of the subplots together in one hugely entertaining masterpiece that gave fans the payoff they demanded.

    It remains a shining example of a spectacle match done right.

4. TLC: Hardy Boyz vs. Edge and Christian vs. The Dudley Boyz (WrestleMania X-7)

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    On the heels of the tag team ladder match at No Mercy 1999 that revived the tag team division and made stars of The Hardy Boyz and Edge and Christian, and the triangle ladder match at WrestleMania 2000 that included The Dudley Boyz, the decision was made to create a new gimmick match featuring the trademark weapons of the three teams.

    At SummerSlam, amid the revival of their rivalry, the teams met in the first-ever Tables, Ladders & Chairs match for the WWE Tag Team Championships.

    Building on spots from previous encounters, the match escalated the risk and violence while highlighting the creativity of the performers involved. The involvement of Lita created the opportunity for new spots and story possibilities, but in the end, the same team that left The Showcase of the Immortals four months earlier reigned supreme in Raleigh, North Carolina, as Edge and Christian emerged battered and beaten, but victorious.

    Within eight months, the teams would again do battle in a TLC match, this time at WrestleMania X-7. That match would surpass their SummerSlam classic, but it was the August 2000 match that introduced the new gimmick bout to the fanbase and perfected it. The 'Mania contest would go on to be as good as it was because it built on the foundation the three teams had laid there.

    That it occurred at a time when tag team wrestling in WWE had peaked gives it the edge over the prequel.

3. Steel Cage Match: Steve Austin vs. Mr. McMahon (St. Valentine's Day Massacre)

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    The entire Attitude Era was built around the anti-authority rebel "Stone Cold" Steve Austin combating the megalomaniacal owner of WWE, Vince McMahon. Fans hung on every angle, match, storyline development and high jinks the two perpetrated on each other. They tuned in to see how Austin would make his boss' life a living hell this week or how McMahon would screw over the blue-collar hero next.

    What they never got, though, was an actual match between Austin and McMahon.

    That changed on February 14, 1999, at St. Valentine's Massacre when Austin beat the ever-loving hell out of his employer in a steel cage main event. The Texas Rattlesnake bumped McMahon off the top of the cage, sending him through an announce table in a spot that broke the tailbone of the evil owner. From there, he unapologetically pummeled McMahon until the massive Paul "Big Show" Wight made his debut.

    The giant manhandled Austin, tossing him into each side of the steel structure until his strength proved problematic and Stone Cold exploded through the wall and dropped to the floor. Austin picked up the win, cashed his ticket to WrestleMania and, once again, thwarted The Chairman's plan.

    A brilliantly worked match that kept the fans in Memphis, Tennessee, enthralled throughout despite its largely one-sided nature, it was exactly what the loyal audience demanded out of the first-time matchup with a nice twist to boot.

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

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    The brutality and violence that took place on June 28, 1998, would forever define the Hall of Fame career of Mick Foley. Whether as Mankind, Dude Love or Cactus Jack, Foley had taken substantial bumps and endured considerable punishment before. What happened that night in Pittsburgh, though, was at an entirely different level.

    First was the bump off the steel structure, unprotected through an announce table some 20 feet below. Then, there was the raw imagery of him climbing back up the cell, his shoulder clearly dislocated, to re-engage his opponent. His reward? A chokeslam through the cell roof, a spot not originally intended to happen, as the mesh gave way under Foley's body.

    Foley unconscious on the mat below, Undertaker looked down at him with bewilderment on his face. When Foley returned to the ring to continue his performance, that bewilderment turned to awe.

    Undertaker ultimately won the match, first sending Foley into a pile of thumbtacks and then delivering a Tombstone. The outcome was irrelevant, though. What mattered was that the loser of the match established a legacy for himself on the grand stage of WWE that is unlikely to be matched, at the expense of his body and career longevity.

1. WWE Championship Match: The Rock vs. Steve Austin (WrestleMania X-Seven)

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    Rock. Austin.

    Two of the biggest, most celebrated Superstars in WWE history collided in the main event of WrestleMania X-Seven, an event many consider the zenith of the Attitude Era. With the top prize in the industry at stake and, arguably, the greatest pre-match video package ever produced accompanying it, excitement was at a fever pitch for the contest.

    A wild, chaotic brawl befitting a match of this magnitude ensued. Dramatic near-falls and breathtaking false finishes kept the fans in Houston's Astrodome engrossed while callbacks to previous encounters and Austin's days as The Ringmaster piqued the interest of even the toughest critic.

    It was the finish, though, that left fans in awe.

    Mr. McMahon, fresh off a loss to son Shane earlier in the show, made his presence felt. In a stunning (yeah, yeah) turn of events, he aided Austin in battering The Rock with a steel chair and capturing the title. The finish stunned commentator Jim Ross, who exclaimed Austin was "shaking hands with Satan himself!" as The Texas Rattlesnake revealed a business relationship with the one man who had been his sworn enemy for half a decade.

    Everything fans knew about the Attitude Era, the certainty that Austin and McMahon would wage war at every turn, changed before their very eyes. It was an earth-shattering moment in wrestling history. Say what you will about where things went from there, but one thing is certain: Try as it did, WWE Creative was never able to capture the lightning in a bottle that made the era so incredibly fun again.

    Technically, the Attitude Era would crawl along for another year, but that period, for all intents and purposes, ended with Austin's deal with the devil.