From the ashes of desperation came WWE’s “Attitude Era”, a time period of amplified storytelling and degradation that spanned from 1997 to 2001. With Eric Bischoff at the helm, WCW was on the verge of conquering Vince McMahon and the WWE with programming primarily focused on wrestling icons that once called WWE home. After losing wrestlers such as Hulk Hogan, “Macho Man” Randy Savage, Scott Hall, and Kevin Nash, WWE (then WWF) carried on with their new generation consisting of Bret Hart, Shawn Michaels, The Undertaker, “Stone Cold” Steve Austin, among ample more. Although there was talent present to showcase, WWE was falling flat creatively after trying to get cartoonish, sophomoric characters to generate with their maturing crowd. As the late, great Owen Hart would have said, “Enough was enough, and it was time for a change.”

This change came in the form of an era that took the former’s prayers and vitamins, set them aflame, and replaced them programming that took full advantage of its TV-14 rating. Network executives may have been upset, but fans were jubilant each and every week as their new brand of wrestling hero spat in the face of authority, rather than respecting it. Now, as we continue to enjoy the “New Era” WWE has given us, let’s take a look back at fifteen matches that defined the “Attitude Era”.

15 15. Bret Hart vs. “Stone Cold” Steve Austin - WrestleMania 13

This “I Quit” match should be considered the one that kicked off the hellacious run of “Stone Cold” Steve Austin, the flag bearer of the Attitude Era. With WCW having their guns aimed towards Stanford, Connecticut, WWE would have been a distant memory if it were not for Austin.

Bret Hart was the WWE’s grizzled veteran, having survived an era completely engulfed by red and yellow smoke. Not nearly has squeaky-clean as Hogan, Hart’s character became confused and bitter about the fans beginning to cling to the villainous Austin (also to his degenerate arch-rival, Shawn Michaels), disregarding that the “Excellence of Execution” was the spokesman of sportsmanship and honor within the wrestling business.

What made this match so important to the Attitude Era was the shifting of roles between Hart and Austin during this match; Hart transitioned into the lead heel of the company, as Austin became the rebellious fan favorite that would go on to be one of the biggest stars in the history of professional wrestling. Hart won the match, but Austin won the hearts of fans everywhere by passing out to Hart’s Sharpshooter rather than choosing to quit.

14 14. Shawn Michaels & “Stone Cold” Steve Austin vs. Owen Hart & The British Bulldog - May 26, 1997: Monday Night Raw

At this point, Steve Austin had developed into a clear fan favorite. He and “The Heartbreak Kid” Shawn Michaels were assumed to be the two lead fan favorites to lead the WWE into the new, more risqué era (later to be dubbed “The Attitude Era”). However, the two were also feuding, which would soon force fans to pick one or the other.

Owen Hart and “British Bulldog” Davey Boy Smith represented The Hart Foundation, the last great faction constructed before the “Attitude Era” would gain its legs. The group’s leader, Bret Hart, was the last representative of traditional professional wrestling. He would determine that the sacrilegious transition into what would be dubbed the “Attitude Era” was representative of America’s core value, inciting civil war within WWE between Canada and the United States. This made this tag team match a pure symbol of new attitude facing the old regime.

In the end, Austin and Michaels would win, gaining the WWE Tag Team Championships. Their reign would not last long, as both men could not co-exist, setting the tone for a path that would soon end the following April at WrestleMania XIV.

13 13. Bret Hart vs. Shawn Michaels - Survivor Series 1997

Regardless of the amazing creative highs (or lows, depending on who was watching) hit by the WWE during the “Attitude Era”, the lasting iconic image of the era will forever be the ringing of the bell at the end of this match, forever to be known as the “Montreal Screwjob”.

Shawn Michaels was the Godfather of the “Attitude Era”. “Stone Cold” will forever be its face, but Michaels and Degeneration-X kickstarted lewd, perverted acts that the time period would be known for. To incite the Montreal crowd, Michaels shoved the Canadian flag down the crotch of his tights, showing not only disrespect to Canada, but to the traditions Bret Hart stood for.

Bret Hart simply did not fit in the “Attitude Era”. The traditions he took seriously (far too seriously at times) were the antithesis of what the next four years would be about, most likely a large reason why Hart was destined for WCW following Survivor Series.

Vince, along with Michaels and Triple H, conjured up a plan to get the belt off of Bret, something Bret was not willing to creatively in an event taking place in Canada. Bret would go on to flounder and have his head blown off by Goldberg, while Michaels would terrorize WWE with Degeneration-x. However, it was in creation of another character that makes this match iconic within the annals of the “Attitude Era”.

In the following weeks, Vince McMahon would become “Mr. McMahon”, starting with his “Bret Screwed Bret” interview. Mr. McMahon was a money-hungry tyrant, willing to do anything to make it known that at the end of the day, he gets what he wants. Dispatching a future Hall of Famer in Bret Hart would be the exposition of a corrupt legacy that would develop in the coming years.

12 12. Steve Austin vs. Shawn Michaels - WrestleMania XIV

At WrestleMania XIV in Boston, the “Godfather” of the “Attitude Era” would pass the torch to the new face of the WWE.

The Attitude Era does not happen without Shawn Michaels. As he said during an in-ring promo when he returned in 2002, he was “’Attitude’ before it was a catchphrase.” Unfortunately, he was the poster boy for attitude both in and out of the ring. On top of being on painkillers much of the time, Michaels was also dealing with bulging disks in his back due to a bump off of a coffin sustained at the Royal Rumble. During the match, his face was definition of distress, making it obvious to the viewers that his back was in no condition to be participating in a match. The injury was so severe that this would end up being his last televised match until Summerslam 2002. Although his moveset was somewhat limited due to his injury, Michaels would show is pitbull-like tenacity and work through the pain.

Even though HBK showed guts few others can, this was Stone Cold’s show. For over a year prior, Austin had been gaining momentum, climaxing during his in-ring altercation with Mike Tyson weeks before this match.

By the time WrestleMania XIV had arrived, Austin has been receiving crowd reactions not heard since The Beatles. After reversing Sweet Chin Music and turning it into a Stunner, Austin pinned Michaels to win the WWE Championship, cementing Austin is the rightful king of the Attitude Era.

11 11. Undertaker vs. Mankind - King of the Ring 1998

“Good God almighty! Good God almighty! He killed him!

Jim Ross’s iconic line is forever stamped to this theater of the insane. In the waning days of the Monday Night Wars, Mick Foley’s body crashing through the Spanish announcer’s table signified the beginning of the end of WCW.

There was no psychology. There was little story being told. On June 28, Mick Foley went to the ring and single-handedly announced that WWE was the superior brand. While WCW was featuring stars of yesteryear, WWE proved that they were willing to provide controversial thrills that no wrestling organization not named ECW was willing to provide.

WCW was never able to duplicate the action seen in this match, and would only claim seven more Monday night ratings victories after this match. WWE truly proved in this match that they were able to provide “attitude” that WCW simply wasn’t.

10 10. Val Venis & Taka Michinoku vs. Sho Funaki & Dick Togo – August 3, 1998: Monday Night Raw

There was nothing scientific or creatively brilliant about this match. Rather, this match was representative of the extreme levels WWE was willing to go to during The Attitude Era.

Val Venis was a character that came to the WWE after a career in the porn industry with a mission to wrestle and get laid. After making rather derogatory comments about Mrs. Yamaguchi-san, her husband declared to Venis that he would “choppy choppy (his) pee pee.” Venis’s first career was most certainly at stake.

This match was brief, seeing Michinoku turn on Venis and join the opposition (which would soon be named Kai En Tai). After the match, Venis was dragged to the back. As Funaki and Togo held up a dazed Venis, Yamagucki-san, samurai sword in hand, approached Venis. The camera panned away to the sound of Venis screaming in pain, implying that his member had been dispatched.

Not much was done with this storyline after this night, and rightfully so. However, WWE was still in the midst of the Monday Night War. This match showed that WWE was willing to do anything to survive their war with WCW.

9 9. Triple H vs. The Rock: SummerSlam 1998

The battles that took place between “Stone Cold” Steve Austin and The Rock providing lasting images that are commonly thought of when one thinks of the Attitude Era. However, many forget that The Rock had his fair share of wars with Triple H as both men rose to the top of the WWE.

This match found both wrestlers in transition periods. The Rock was leading The Nation of Domination, but gaining main event heat from fans thanks in part to the verbal lashings his dispersed on whomever he pleased. Triple H was the leader of Degeneration-X, a position he assumed upon the departure of Shawn Michaels after WrestleMania XIV. Now, he would be competing for the Intercontinental Championship in a ladder match, a match his best friend made famous years prior.

At WrestleMania X, Michaels and Razor Ramon (mostly Michaels) put on a bit more of an athletic display in their match. However, this matchup between Triple H and The Rock provided vicious, brawling action the Attitude Era was known for. In the end, Triple H would prevail, continuing his ascension to the top of the WWE, as The Rock would move on to the main event, a spot that he would never relinquish.

8 8. The Rock vs. Mankind – January 4, 1999: Monday Night Raw

The Rock and Mankind had infamous, brutal matches that spanned throughout much of the Attitude Era. The classic wrestling documentary, Beyond the Mat, featured Foley taking repeated violent chair shot in front of his children. During halftime of Super Bowl XXXIII, both competitors competed in a revolutionary empty arena match for the WWE Championship. However, none of their matches were as polarizing as the one that produced Mick Foley’s first, and unprecedented, WWE Championship reign.

Foley’s long climb to the top of professional wrestling had been showcased in weeks leading up to this episode of Monday Night Raw. His underdog story gained the affection of fans, an affection that blossomed further the more the McMahons attempted to hold him down. After assistance from “Stone Cold” Steve Austin, Mankind pinned The Rock for the belt, resulting one of the biggest crowd pops in WWE history.

This match would live in further infamy, as Eric Bischoff’s habitual revealing of Raw results on WCW Monday Nitro would blow up in his face. After Tony Schiavone sarcastically revealed Foley would win the belt, stating “That should put some butts in the seats”, Nitro viewers almost immediately, in unison, switched over the Raw. The beginning of the end was near for WCW.

7 7. “Stone Cold” Steve Austin vs. Mr. McMahon - St. Valentine’s Day Massacre

Fans will forever remember the iconic battles between Austin and The Rock.

Make no mistake, however. The headlining feud during the Attitude Era was “Stone Cold” Steve Austin vs. Vince McMahon.

For years, McMahon ran the company while only appearing on screen as a color commentator. He began to receive more attention as owner during the initial Degeneration-X run, when Shawn Michaels and Triple H projected the infamous Madison Square Garden “Curtain Call” for Kevin Nash and Scott Hall, infuriating McMahon on screen. Then, he called for the bell during the “Montreal Screwjob”. McMahon was advertised as a corrupt boss unwilling to utilize flexibility as the content within the business changed. Thus, Mr. McMahon was born.

There was no bigger spearhead for the Attitude Era than Steve Austin. This created obvious disconnect for Mr. McMahon’s character, causing McMahon to begin a years-long siege to cease the pop culture juggernaut that was “Stone Cold”.

This came to a head at St. Valentine’s Day Massacre, a violent, bloody match that basically saw Austin beat the tar out of Vince. Halfway through the match, Vince took a bump off of the side of the cage and through the announcer’s table, showing that he was truly ready to do whatever was necessary to ensure his company’s success. He would later draw Austin back into the ring after trying to escape the cage by issuing multiple middle fingers, showing that McMahon has completely crossed over to the dark side.

This match also saw the debut of Big Show, formerly “The Giant” in WCW, one of the first notable cross-overs from WCW to the WWE.

6 6. Bart Gunn vs. Butterbean – WrestleMania XV

More often than not, the creative liberties taken by WWE creative writers paid off. The “Brawl for All” tournament was not one of those times.

For weeks, a legitimate boxing tournament was held on episodes on Monday Night Raw involving inexperienced WWE wrestlers. Participants have since called this the worst idea of the Attitude Era, as multiple injuries came as a result of this tournament. In the end, Bart Gunn won the tournament, and his reward was to face Butterbean at WrestleMania XV. The result of this would be a quick knockout of Bart Gunn, ending the Attitude’s Era’s greatest creative dud.

5 5. Gerald Brisco & Pat Patterson vs. The Mean Street Posse (Loser Leaves the WWE) – May 10, 1999: Monday Night Raw

The popularity of Vince McMahon’s former “stooges” was a prime example of how the Attitude Era awarded creativity more so than in-ring work.

Patterson’s and Brisco’s sole purpose was to create comedy during the Attitude Era. They competed in evening gown matches, and Briscoe even soiled himself in the ring. Their unique brand of entertainment caught fire with the fans after they left the side of Mr. McMahon.

Mr. McMahon’s former stooges began a feud with Shane’s, The Mean Street Posse. This match drew what is rumored to be the highest television rating not only of the Monday Night Wars, but of professional wrestling as a whole. The end result of the match was even better than the rating, as Patterson and Brisco were victorious, allowing fans to no longer be subjugated to the unorganized ring work of The Mean Street Posse.

4 4. Triple H vs. Cactus Jack - No Way Out 

Not only was the envelope pushed during the Attitude Era in regards of taste, but also in regards of violence. Mick Foley, in all of his incarnations, is the poster boy for violence during the Attitude Era. However, the chair shots and dangerous falls took their toll on Foley, and this match served as the official torch passing between he and Triple H.

Sensing that the end was near, Foley, appearing as Cactus Jack, decided to put his career on the line. Despite his immense accomplishments, Foley had yet to headline a Wrestlemania. After years of physical abuse, Foley knew that his body had just about expired, giving him one last shot at the ‘Mania main event.

This match is Mick Foley at his finest. His world-renowned tolerance for pain was put on full display through violent whips into the cell and chair shot, giving Triple H the shine was a rightful heir to Foley’s mantle of aggression.

The climax of this match would once again find Foley on top of Hell in Cell. First he would fall through the announcer’s table after dangling from the side of the cell. After making his way back to the top of the cell, Foley would set his barbed wire 2x4 on fire and use it as a weapon. Finally, after taking a backdrop from Triple H, Foley crashed through the top of the cell and then through the ring, allowing Foley to have one last defining moment of violence before walking off into the sunset.

3 3. Triple H vs. Chris Jericho – April 2, 2000: Monday Night Raw

The Attitude Era was a time in which the WWE created many new stars. After being cast aside for older talent in WCW, Chris Jericho arrived in the WWE ready to make an impact. This night in April of 2000 would serve as Jericho’s first of an infinite number of iconic moments in his WWE career.

The McMahon-Helmsley Era was in full effect, and Jericho was not playing nice, especially with Stephanie (with some of the greatest insults professional wrestling has ever seen). Egging Triple H on by saying that it would impress Stephanie, Chris Jericho convinced Trips to put his WWE Championship on the line to open the show.

This match had a plethora of “Attitudinal” moments, including fans chanting “slut” at Stephanie, and “Shane’s a pu…” Well, let’s just say in was not flattering.

What makes this match so “Attitude Era” is the multiple plot lines that were present in this match. Jericho had been verbally terrorizing the McMahon-Helmsley regime. Triple H and Stephanie were in their embryotic stages of keeping everyone under their proverbial boot. Jericho hired the APA as an insurance policy in the event of tomfoolery taking place during the match. Finally, Senior Referee Earl Hebner had been bullied by the McMahon-Helmsley regime in weeks, and provided the fast three count to give Jericho the win and the title in the match (providing one of the biggest pops in Raw history).

Jericho was not able to keep the title due to Hebner’s fast three count, but a true rebellious superstar was born in Chris Jericho, a perfect addition to the Attitude Era, and who would grow to become a legend in the annals of the WWE.

2 2. Edge & Christian vs. The Hardy Boyz vs. The Dudley Boyz –WrestleMania X-Seven

In an era that was ruled by a select number of superstars, this match may be the one fans remember most that did not take place in a cell.

The three teams in this match carried with them a fan following that came close to challenging anyone in the main event scene. Edge and Christian were heels, but acquired fan admiration due to their hilarious and creative segments (many of them being “five seconds” long). The Dudley Boyz were willing to destroy everyone, including Mae Young, and brought a loyal ECW fanbase to the WWE. The Hardy Boyz had, at a minimum, bi-nightly highlight reel performances, and a female manager that received fan pops bigger than their own. All three popular teams would revolutionize the industry in this match.

All competitors were proven to be innovative mad scientists in this match. Barely a moment went by that didn’t find a competitor being decimated, but all moments were impactful to the match, even the interferences from Spike Dudley, Rhyno, and Lita.

The climax of the match would involve the most picture-perfect spear of Edge’s career. As Jeff Hardy was dangling from the belt apparatus without a ladder under him, Edge jumped from a top of a ladder and speared Hardy about fifteen feet to the mat. Thank to this moment, among many others in this match, all teams were winners, as each career was partially defined by being associated with it.

1 1. “Stone Cold” Steve Austin vs. The Rock - WrestleMania X-Seven

After all of the wars these two fathers of the Attitude Era, one may ask, “Why does this one make the list?”

The answer is simple. When “Stone Cold” Steve Austin shook hands with his arch-nemesis, Mr. McMahon, at the end of this match, he put the final death nail into the coffin of The Attitude Era.

The rivalry between Austin and McMahon headlined The Attitude Era. If this list would have covered “The 15 Defining Moments of the Attitude Era”, those two would have conquered at least half the list. However, this list is not about moments, but about matches, and this Austin/Rock war was the most impactful of all of them.

From the beginning of the bell, there was not a second to be spared for fans to get pictures taken, as the two rivals begin swinging as soon as the bell rang. This back-and-forth exchange would continue, until Vince McMahon would shockingly interfere on behalf of Austin. After stunners and chair shots, the lopsided onslaught became too much for The Rock, as Austin would go on to win his WWE Championship.

After a handshake between Austin and McMahon, it was clear that the WWE would never be the same again. After a four-year plight against almost everything “attitude”, McMahon would prove that the McMahons always win, even bringing the Attitude Era’s great rebel “Stone Cold” Steve Austin over to the dark side. That handshake signaled the end to not only to one of professional wrestling all-time great rivalries, but the “Attitude Era” that was an orchard creativity and boundary busting that may never be seen again.