Ranking the 25 Most Unforgettable Moments of WWE's Attitude Era

The Attitude Era.

It is, arguably, the most popular period in professional wrestling history and a breeding ground for the most unforgettable moments produced by WWE. Beginning with Vince McMahon's controversial promo in December 1997 ushering in the era and running through The Chairman's June 2002 promo introducing the Ruthless Aggression Era, its impact on the history of pro wrestling is well-documented.

Rife with in-your-face bravado, middle finger-flipping antiheroes and sheer chaos, it was an era that many have tried to duplicate but never will, thanks to several factors that include a more family-friendly direction and sponsorship deals.

It made stars of castoffs, such as "Stone Cold" Steve Austin and Triple H, and introduced the entertainment industry to The Most Electrifying Man in All of Entertainment, The Rock. It frequently flirted with the fine line between entertainment and bad taste—and occasionally obliterated it.

Regardless, its effect on the industry and its place in the annals of wrestling history is undeniable.

As Bleacher Report kicks off its week-long salute to the Attitude Era, relive these 25 moments that helped define it and made for some of the most exciting, enjoyable and memorable television of all time.

December 13, 1999 (Raw)

Just 24 hours after the Armageddon pay-per-view, in which Stephanie McMahon betrayed her father and sided with her new husband, The Billion Dollar Princess confronted the emotionally broken Mr. McMahon to explain her actions.

Citing the time earlier in the year when McMahon used her as a pawn in her war with Steve Austin, she revealed the best way she knew to get back at him was to marry the man he hates.

"Triple H really turns me on," she said, with a smile across her face as she walked away from her father.

The moment may seem small, but it ignited the McMahon-Helmsley regime that would go on to engulf the year 2000 in WWE.

Whether the happy couple stood alongside McMahon after a reunion of sorts later in the spring or ruled the roost on their own, they were integral to the most acclaimed 12 months in the company's history and were responsible for any number of unforgettable moments, not least of which was the love triangle with Kurt Angle.

April 17, 2000 (Raw)

Rarely is a close call with championship gold as memorable as a Superstar's actual title win, but that was the case for Chris Jericho on the April 17, 2000 episode of Raw.

Goading Triple H into a title defense by insulting his wife, Stephanie McMahon-Helmsley, Y2J set out to capture a title he spent his childhood tracking from Hulk Hogan to Randy Savage to Ultimate Warrior. 

With The APA's Bradshaw and Faarooq negating the interference of Shane McMahon, a frustrated Triple H shoved referee Earl Hebner. The distraction allowed Jericho to catch him with a heel kick and then the Lionsault. Hebner recovered, counted a fast three and awarded Y2J the win and title.

Except, the vengeful three-count from Hebner was deemed unfair by both The Game and fellow referee Mike Chioda, and the outcome was overturned. Jericho returned the title begrudgingly, and Triple H fired and pummeled Hebner.

The reaction from the fans in State College, Pennsylvania, erupted for the Jericho victory, suggesting to both the performer and management alike that he was poised to be a hugely popular star for the company.

Perhaps more importantly, it was proof that fans would embrace Jericho as the top champion in the promotion, a role he was never once considered for in WCW.

August 20, 2001 (Raw)

Just 24 hours after being screwed out of the WWE Championship by crooked official Nick Patrick and "Stone Cold" Steve Austin, a vengeful Kurt Angle interrupted Stone Cold Appreciation Night by driving a milk truck into the arena.

Taking a page out of Austin's book, he pulled out a hose and proceeded to spray down the entire Alliance with milk, leaving Austin, Stephanie McMahon and the rest of the heel faction soaking wet and dismayed.

"Milk-o-Mania is running wild!" Jim Ross exclaimed on commentary, making the moment even more memorable.

Yes, it was a direct ripoff of Austin spraying down The Corporation with beer two years earlier, but the fact it was done in retaliation to him, and played to the wholesome nature of the Angle character, made it a delightful addition to the pantheon of Raw memories and one of the great moments of the Attitude Era.

July 9, 2001 (Raw)

The WCW invasion of WWE in 2001 fizzled out miserably from the outset, thanks to a lack of star power and a disastrous first main event between Booker T and Buff Bagwell.

Sensing the high-profile, hotly anticipated storyline needed an injection of excitement to keep it relevant, WWE Creative revived another promotion: ECW.

On the July 9 episode of Raw, a faction of former ECW stars betrayed their WWE brethren and beat them down, introducing a third brand to the war for company supremacy. What the Superstars of WWE never imagined was that an unholy alliance between WCW and ECW had been forged by their owners: Shane and Stephanie McMahon.

An attempt to get back at their father and prove they were able to do what no other promoter could by beating Vince once and for all, they banded together to provide the greatest threat to WWE's existence ever.

At least for a few weeks, that is.

Still, the inconsistency and disappointment of the Invasion storyline did not take away the genuine surprise and excitement that surrounded the introduction of the extreme company and its unforeseen union with WCW.

February 17, 2002 (No Way Out)

Driven to madness by his co-owner of WWE, Ric Flair, Vince McMahon vowed to destroy his own company by injecting it with a "lethal dose of poison."

That poison? The New World Order of Hulk Hogan, Kevin Nash and Scott Hall, the same trifecta of Superstars that nearly destroyed WCW from the inside.

At the February pay-per-view, No Way Out, the trio made its long-awaited return to the company that made them household names. Showing fake sincerity, they addressed the WWE fans, claiming to be interested only in contributing and making the company better.

By night's end, a screwjob of Steve Austin would prove otherwise while simultaneously setting up one of their major rivalries ahead of WrestleMania X-8.

The moment was surreal. The idea that McMahon would lean on the star power of Hogan, Hall and Nash to revive television ratings despite the issues they caused in WCW was fascinating.

Although the backstage controversies did not accompany them this time, though, they never really proved to be the difference-makers the company had hoped.

December 9, 2001 (Vengeance)

The conclusion of the Invasion storyline left WWE with two distinct world titles: its own and the WCW Championship.

With no need for them, the company announced the Vengeance pay-per-view would crown the first-ever undisputed champion of WWE.

The Rock, "Stone Cold" Steve Austin, Chris Jericho and Kurt Angle would vie in three matches to crown the new titleholder.

Austin downed Angle in the first match of the trio, while Jericho capitalized on outside interference from Vince McMahon to defeat The Rock.

Y2J, still battered from the near 30-minute bout against The People's Champion, battled Austin for the right to etch his name in the history books.

Thanks to more interference, this time from Booker T, Jericho won the match and forever earned bragging rights as not only the first undisputed champion, but also the only man to beat Rock and Austin on the same night.

April 1, 2001 (WrestleMania X-7)

"I need to beat you, Rock. I need to beat you more than you could ever imagine."

"Stone Cold" Steve Austin warned the world of what was to come at WrestleMania X-7 when he challenged The Rock for the WWE Championship in the night's star-studded main event.

Austin, headlining his first Showcase of the Immortals after missing a year of action while rehabbing his neck, was hellbent on leaving Houston with the championship he once called his own.

Few could have expected the depths to which he would go to make his goals a reality.

Late in the bloody battle with The Great One, Vince McMahon made his way to the squared circle, clearly intent on interfering. No one could have imagined he would side with Austin, working hand-in-hand with The Texas Rattlesnake to beat, batter and pummel The Rock into oblivion before Stone Cold could win the title.

A stunned Jim Ross would exclaim Austin was "shaking hands with Satan himself," as the two revealed their plan to the world.

While Austin's heel turn would largely be considered a failure, there is no denying the impact of that moment. The Attitude Era as we knew it, born from Austin's rage against the political machine in WWE, had come to an end when he made his deal with the devil. 

We would have Austin vs. McMahon many times after, but it lacked the same impact of the years-long rivalry that preceded the shocking conclusion to the best WrestleMania of all time.

October 12, 1998 (Raw)     

A week after attacking Mr. McMahon in hospital, "Stone Cold" Steve Austin rolled into Raw looking to add insult to injury.

Driving a cement truck into the arena, he stopped just shy of McMahon's prized Corvette and proceeded to fill it with hundreds of pounds of concrete.

The billionaire owner of WWE watched in horror as the windows of his vehicle exploded under the weight. The crowd popped at the blatant sign of disrespect and rebellion, as Austin again got one over on the boss man.

November 15, 1998 (Survivor Series)

Arguably the greatest tournament in WWE history took place at the 1998 Survivor Series. The company's heavyweight title had been held up after a controversial finish to a match between Undertaker and Kane to crown the new champion.

Over the course of the Survivor Series pay-per-view, Superstars vied for the opportunity to win the title, but the tournament setting also allowed Vince McMahon and Vince Russo to tell numerous stories over the course of the evening. Everything from Goldust's ongoing rivalry with Val Venis to McMahon's newfound issues with The Rock took center stage.

It was the feud with Rock and the outliers that dominated the evening.

First, McMahon promised Mankind he was the hand-picked champion. Then, he proved it by screwing Steve Austin out of the title in the semifinals. All the while, he put obstacle upon obstacle in The Rock's path, only to watch The Great One emerge victorious each time.

When the tournament came down to Rock and Mankind, it appeared fairly certain the latter would win in yet another Survivor Series screwjob.

At least part of that assumption was right.

Rock trapped Mankind in the Sharpshooter, and McMahon called for the bell. For the second year in a row, a beloved Superstar was screwed out of the title by a conspiracy headed by The Chairman.

Vince stood in the center of the ring and engaged Rock and son Shane McMahon in a group hug, the trio proud of their actions and happy with the plan's execution.

No longer was The Rock the self-proclaimed "People's Champion." Instead, he was the "Corporate Champion," a selfish heel worried only about himself and his own career advancement.

He was also the villain around whom WrestleMania plans would be booked and the top bad guy in the cross hairs of a vengeful Mankind and Austin.

January 30, 2000 (Raw)

Like Chris Jericho just months earlier, the creatively and professionally frustrated Chris Benoit, Perry Saturn, Dean Malenko and Eddie Guerrero opted to leave Ted Turner's company for the new pastures of WWE.

The January 30 episode of Raw saw the quartet appear at ringside during a match between The New Age Outlaws and Steve Blackman and Al Snow, and they wasted no time making their presence felt. They attacked Road Dogg and Billy Gunn when antagonized, swarming upon the tag team champions.

It was an announcement to the wrestling world that things had changed: They were no longer willing to sit back and wait their turn.

They made an immediate impact on their first night with the biggest wrestling promotion in the world and would continue to star for WWE, particularly Benoit and Guerrero, who would become world heavyweight and WWE champions, respectively.

October 17, 1999 (No Mercy)

Never before had a woman won a men's championship in professional wrestling when Chyna entered the Good Housekeeping Match at No Mercy 1999. Her opponent that night was the chauvinistic intercontinental champion, Jeff Jarrett.

After weeks of listening to the loudmouthed Jarrett decry the role of women outside of the kitchen, Chyna sought to silence him and accomplish a goal Vince McMahon Sr. could never have imagined when he brought the title into existence.

She did just that, overcoming attempted interference from Miss Kitty to capture the coveted IC title.

That accomplishment alone makes Chyna a credible Hall of Famer. That she won the title one more time, less than a year later bolsters the idea.

As for her place in the Attitude Era, she was a member of D-Generation X, stood by Triple H's side as he won his first world title and then became a major crossover star in her own right, which catapults her up the list of that period's greats.

January 7, 2002 (Raw)

Eight months. That's how long Triple H spent on the sidelines, rehabbing diligently from a torn quadriceps muscle that could have cost him his career.

As his return drew nearer, video packages set to U2's "Beautiful Day" aired, detailing the rigorous rehabilitation he went through to get back in the ring.

The excitement for The Game's comeback built with every passing week until it was announced that he would return on the January 7 episode of Raw, emanating live from the most famous arena in the world, New York's Madison Square Garden.

As the opening chord of Motorhead's "The Game" exploded over the PA system, the fans in MSG erupted with one of the loudest sustained ovations in WWE history.

Once the most hated man on the roster, Triple H made his way to the squared circle, amped up over the realization that the fans had not forgotten him.

"I am The Game and you can bet your ass I'm back!" he exclaimed. The crowd popped and all was right with WWE.

March 26, 2001 (Raw)

There are few moments that can be considered milestones in wrestling history, but the March 26, 2001 episode of WWE Raw is one of them.

In a simulcast also airing on TNT as part of WCW Nitro, Vince McMahon announced to the world that the entire wrestling industry was in his hands after he purchased Ted Turner's company, effectively ending the Monday Night War.

The braggadocious McMahon strutted to the ring and addressed both companies, leaving the fates of several top stars up to the fans. So egotistical, he claimed he would have Turner come to the ring at WrestleMania X-7 and sign the contract. 

Of course, such a claim suggested the contract had not yet been signed, something we would learn quickly wasn't the case.

Amid a personal rivalry with his father, Shane McMahon appeared in Panama Beach, Florida, at Nitro and revealed he had bought the company out from underneath his father.

The segment would add significant heat to a feud between the two men that already had several layers and elements surrounding it while providing an unforgettable angle to a hugely historic event.

October 5, 1998 (Raw)

After enduring a brutal and vicious assault at the hands of Undertaker and Kane that left him hospitalized with a broken ankle, Mr. McMahon appeared on the October 12 episode of Raw, live from his sickbed.

Irritable and difficult, he insulted nurses and doctors until Mankind visited with Yurple the Clown and something that would become a major element of his performances for the remainder of his career, the debuting Mr. Socko.

The exclamation point on the vignettes came when Steve Austin popped up, clad in medical scrubs, and attacked McMahon. He bashed him over the head with a bed pan and proceeded to shove a thermometer where the sun doesn't shine.

It was another example of Austin getting one over on the boss in hysterical fashion, all while introducing the world to the surprisingly over sock puppet.

June 7, 1999 (Raw)

The Undertaker's formation of The Ministry of Darkness forced enemies to become allies in 1999, most notably Steve Austin and Mr. McMahon.

After two years of hostility, they found themselves on the same side of a battle with The Deadman and his minions. Austin even saved McMahon's daughter, Stephanie, from marrying Undertaker in a dark ceremony.

When it was announced The Greater Power behind Undertaker's actions would be revealed, the wrestling world wondered who could possibly be so evil as to dictate his every move.

Maybe it was Jake "The Snake" Roberts? Perhaps it was some WCW star defecting from that company and debuting in WWE? Whatever the revelation, it was sure to be awesome, right?

The Higher Power made his way to the ring and removed his hood to reveal...McMahon.

It was all a ploy to screw with Austin, to lure him into a false sense of security and take the WWE Championship. It worked until it cost McMahon his role as CEO, which was awarded to The Texas Rattlesnake by Linda and Stephanie McMahon.

An unforgettable Attitude Era moment, the reveal still ranks among the greatest disappointments in wrestling history.

August 9, 1999 (Raw)

For weeks, the millennium clock ticked down, inching closer to zero as fans wondered what the grand reveal would be when it did. They found out on the August 9, 1999 episode of Raw as pyro exploded atop the entrance ramp and the name "Jericho" appeared on the Titantron.

The fans erupted as Chris Jericho, formerly of WCW, made his WWE debut, interrupting The Rock's in-ring promo.

The newcomer promised to save the fans from the monotony of the WWE product, including The Rock. The loudmouthed Y2J spewed verbiage until The Great One shut him down and not-so-warmly welcomed him to the company.

Even though it may not have ended as he imagined, Jericho's debut ranks among the greatest of all time. From the moment he set foot on Raw, he was perceived as a star worthy of sharing the screen with Rock.

Given the fact that he was deemed not big enough in WCW, in stature nor star power, his arrival in WWE was a monumental one that made the Winnipeg native a star on his first night, and his work from there on kept him at the top for the entirety of his 18-year run with the company.

November 19, 1999 (Raw)

After weeks of storyline stalling due to the departure of head writer Vince Russo, the long-awaited wedding of Test and Stephanie McMahon finally took to the squared circle on the November 19, 1999 episode of Raw.

Prior to the nuptials, vignettes aired throughout the evening recapping Stephanie's bachelorette party, where she was served a drink by a cocktail waiter. Later in the night, as the pomp and circumstance of the ceremony commenced, a sense that a major twist would occur hung over it like a dark cloud.

Then it happened.

Just as the preacher was poised to announce the newlyweds, Triple H interrupted and aired a video from the previous weekend, in which he wed an unconscious Stephanie at a drive-thru ceremony in Vegas.

With the bride in tears, the antagonist called Vince McMahon "dad," much to the boss' chagrin, and ended by stating, "Not did we, but how many times did we consummate the marriage?"

While it took a long time to get there, and the creative leading up to it was suspect (amnesia, really), the angle it all culminated with remains one of the best heel moments of all time and instantly elevated Triple H's stock within the company.

Without it, and the ensuing relationship with Stephanie both on and off the screen, who knows if we would have be celebrating his 25th anniversary with the company.

March 30, 1998 (Raw)

On the heels of Shawn Michaels' loss to Steve Austin at WrestleMania XIV and his subsequent departure from television as he sought to recover from a serious back injury, D-Generation X was left in limbo.

This rude, crude and lewd faction formed by Michaels and Triple H had become such a significant part of programming that it simply couldn't fade to obscurity, right?

Just 24 hours after the biggest show of the year, The Game assumed leadership of the stable and introduced the returning Sean Waltman (X-Pac) as its newest member. Later in the broadcast, they joined The New Age Outlaws in a brutal beatdown of Cactus Jack and Chainsaw Charlie, signaling the addition of "Badass" Billy Gunn and "Road Dogg" Jesse James to the team.

That group, along with Chyna, would go on to define DX and run roughshod over WWE throughout the Attitude Era—both as babyfaces and heels—en route to achieving Hall of Fame notoriety in 2019.

March 29, 1998 (WrestleMania XIV)

"The Austin Era has begun!" Jim Ross exclaimed on commentary as Stone Cold scaled the ropes and threw his arms up in the air, with the WWE Championship in his hands.

It was the perfect call and visual to represent the passing of the torch from New Generation star Shawn Michaels to the man who would define the Attitude Era in WWE.

Austin had overcome an injured neck and uncertainty surrounding his ability to return to the ring and achieve his goal of capturing the top prize in Vince McMahon's empire.

That he was able to do it standing side-by-side with Mike Tyson only ensured he would be front and center in every newspaper and on every telecast, elevating his star beyond wrestling and making him a household name.

In terms of the Attitude Era as a whole, it was the coronation of its face and the Superstar who would lead WWE to unprecedented success.

January 4, 1999 (Raw)

It wasn't unusual that the Monday Night War brought with it pointed barbs between WWE and WCW's commentary teams.

It began in 1995 with Eric Bischoff reading off the taped results of Raw and continued over the years, with WWE's Jim Ross rarely missing an opportunity to knock the opposition's rather aged main event scene.

The January 4, 1999 episode of Raw was taped, and WCW looked to redirect that show's audience to its own. Through a headset, Bischoff encouraged Tony Schiavone to spoil the company-altering conclusion to that night's main event, in which Mankind would defeat The Rock to capture the WWE Championship.

Schiavone did just that, throwing in, "Ugh, that'll put a lot of butts in seats" for good measure.

As it turned out, 600,000 viewers switched over to Raw to witness the historic title change, giving Vince McMahon's company the victory in that night's ratings battle.

It also highlighted how poorly executed Nitro's main event (the dreaded Fingerpoke of Doom) was and spelled the end for Ted Turner's company.

As Mankind celebrated the realization of his lifelong dream, sprinting around the ring and exclaiming, "Big daddy-o did it," WCW could not have realized the fatal blow it had dealt itself, making the moment as memorable for the historical significance as it was for Foley's triumph. 

April 13, 1998 (Raw)

After 83 weeks on the losing end of the Monday Night War between WWE Raw and WCW Nitro, Vince McMahon stepped inside the squared circle as an active competitor for the first time.

His opponent? "Stone Cold" Steve Austin, the rebellious WWE champion who basked in every attempt The Chairman made to make him the corporate champion in his image. After weeks of mounting tensions, the two agreed to settle their differences in the ring.

Eager to witness the anti-authority badass get his hands on the smug businessman owner of WWE, fans flocked to the USA Network to see the epic encounter.

Of course, it wound up being a bad case of bait-and-switch as McMahon ordered Austin's hand tied behind his back and then watched as the returning Dude Love brutally assaulted the champion, but it still provided the company with an idea of just how appealing the Austin-McMahon feud was.

June 28, 1998 (King of the Ring)

The rivalry between The Undertaker and Mankind, and its physical nature, would lay the groundwork for the style adopted by many throughout the Attitude Era.

At the 1998 King of the Ring, they would rekindle their program in a match that promised brutality and violence the likes of which WWE fans could never have imagined.

Undertaker, working on a broken foot himself, scaled the cage and met Mankind up top to start. The two rivals brawled up there before The Deadman sent his opponent sailing off the roof and through the announce table some 20 feet below. His body mangled and punished, and his shoulder dislocated, it appeared as though Mick Foley's night would end before it ever got started.

But that is where the legend of Foley begins.

With one arm, he climbed back to the top of the cage and continued the fight. This time, Undertaker grabbed him by the throat and delivered a chokeslam, sending him crashing through one of the roof panels and to the mat below in a spot that wasn't intentionally part of the layout.

Despite attempts by his best friend, Terry Funk, to get him to call it a night, Mankind continued to fight...right up through Undertaker slamming him into a bed of thumbtacks. The Tombstone would put him down for the count but the loss mattered not.

All that mattered was the newfound respect the fans and his peers had for Foley. No longer an afterthought who was overshadowed by the likes of Steve Austin, he was a cult hero for the punishment he was willing to take in the name of entertaining the masses.

No one could imagine it beforehand, but that night in Pittsburgh and the performance by Foley would define his Hall of Fame career forever.

April 27, 1998 (Raw)

The newly formed D-Generation X, determined to fire the strike first in the war with WCW, invaded the company's Monday Nitro taping at the Norfolk Scope in Virginia.

Arriving on the scene in a jeep, complete with a cannon, the faction insulted the opposing company at every turn, even getting fans to reveal they got their tickets for the show free of charge.

The surreal sight of WWE Superstars actually invading WC, and airing it on their television show, was unlike anything fans had seen before. It would not be the last time DX made their presence felt at the competition's expense.

In the weeks that followed, footage would air of the Triple H-led group invading WCW offices and CNN headquarters in Atlanta. The controversy of it all fit the faction's attitude and proved that nothing was sacred as WWE fought back in what had been a one-sided ass-kicking by WCW in the Monday Night War.

It was at that point that the wrestling world knew that in terms of WWE's newfound attitude and approach to professional wrestling, there were no rules.

January 19, 1998 (Raw)

Just 24 hours after the 1998 Royal Rumble, former heavyweight boxing champion Mike Tyson came face-to-face with "Stone Cold" Steve Austin.

The Texas Rattlesnake interrupted Mr. McMahon's announcement regarding the boxer's role at WrestleMania and cut a scathing promo that concluded with him flipping Iron Mike the middle finger.

A pull-apart shoving match ensued, and within hours, every major media network and sporting news outlet had video of the scuffle on air. Suddenly, people who had no desire to watch wrestling were intrigued by the idea of the loudmouthed Texan going toe-to-toe with the most recognizable badass in the boxing world.

The publicity made the angle worthwhile and created the most buzz for a WrestleMania event since Lawrence Taylor squared off with Bam Bam Bigelow.

"You ruined it, damn it!" Vince McMahon could be heard yelling as company officials pulled Austin to the arena floor and away from the guest of honor.

It was yet another hint at the rivalry between Stone Cold and McMahon that would engulf the Attitude Era and lead WWE back from the brink of extinction in the Monday Night Wars.

March 22, 1999 (Raw)

Just six days before WrestleMania XV, Stone Cold interrupted a promo by WWE champion The Rock, Vince and Shane McMahon by driving an enormous beer truck down the aisle. Standing atop the cab, he vowed to roll into Philadelphia and burn the SmackDown Hotel to the ground.

From there, he produced a hose and proceeded to douse The Great One, the chairman and the prodigal son in beer.

What was already memorable was made even more so by Vince breaking out the freestyle and swimming in the booze.

Of all the vehicles driven into the arenas across the country by Austin and all of the humiliation dished to his rivals, the beer truck remains one of the most blatant, in-your-face examples of attitude courtesy of the company and its rebellious face.

Stay tuned to B/R throughout the week for more WWE Attitude Era content as we celebrate the wildest, most unpredictable, and out-of-control period in WWE history.