The 20 Icons of The Attitude Era

The 20 Icons of The Attitude Era

What is “Attitude”? For countless members of the WWE Universe, the word is synonymous with the most contentious, chaotic and controversial time period in all of WWE history. But which Superstars truly defined The Attitude Era? Who can rightfully claim responsibility for WWE’s triumph over WCW in the so-called “Monday Night War” of the 1990s? Who gave Mr. McMahon more headaches, D-Generation X or “Stone Cold” Steve Austin?

Delving into the age of Stunners, five-second poses, marker-smeared sock puppets and eyebrow-raising behavior, lists off the 20 icons who truly brought “Attitude” to The Attitude Era.

#20 The Acolytes Protection Agency (APA)

The 20 Icons of The Attitude Era

Former members of The Undertaker’s Ministry of Darkness, Acolytes Faarooq & Bradshaw would later offer their uniquely brutal skill set to any Superstar who needed protection from harm — for the right price, of course. Going into business as The Acolytes Protection Agency, or APA for short, Faarooq & Bradshaw became cigar-chomping, beer-swilling mercenaries, enlisted by their fellow Superstars to serve as bodyguards whenever they weren’t pulverizing opponents in the ring (or at the poker table).  Among the hard-hitting mercenaries’ diverse clientele were Crash Holly, Mae Young, Kaientai and even The Mean Street Posse. Yes, that Mean Street Posse.

Trashing Superstars and barrooms alike, The APA is remembered as one of the most feared tandems of The Attitude Era, earning three World Tag Team Championships and competing in hellacious clashes with the likes of The Dudleys, Edge & Christian, The New Age Outlaws and the buttoned-up critics of all things Attitude Era, The Right to Censor.


#19 Shane McMahon

The 20 Icons of The Attitude Era

“I don’t listen to you anymore.”

With that in-ring proclamation to his father, Mr. McMahon, on the Oct. 26, 1998, edition of Raw, Shane McMahon cemented himself as his own man while the entire WWE Universe looked on. Stepping out of his father’s imposing shadow, Shane was determined to forge his own path, even going so far as to team up with his sister Stephanie to challenge their father for control of WWE in the WCW/ECW Invasion of 2001. Despite their differences, however, Shane and The Chairman did see eye-to-eye on occasion, with Shane’s Royal Rumble 1999 training sessions with dear old dad bringing the WWE Universe some of The Attitude Era’s most laugh-out-loud moments.

Shane was nothing to laugh about in the ring, however, displaying incredible athleticism and the cat-like reflexes befitting his sports-entertainment upbringing. Spectacularly putting his body on the line against some of WWE’s most formidable Superstars, Shane-O-Mac would earn victories over X-Pac, Big Show, Kurt Angle and Steve Blackman, capturing the European and Hardcore Titles in the process.


#18 Goldust

The 20 Icons of The Attitude Era

If you weren’t the least bit creeped out by Goldust during The Attitude Era, you must not have been paying attention. Flummoxing opponents with his strange attire and freakish, unpredictable behavior, this gold-and-black–hued horror show used his twisted mind games to earn an impressive 11 championships in WWE, including the Intercontinental, Hardcore and World Tag Team Titles. Much of Goldust’s early success was attributed to a little maneuver he called “Shattered Dreams,” and … you know what? It’s painful just thinking about that one, especially if you possess a pair of “golden globes.”

Even more head-turning than The Bizarre One’s in-ring accomplishments were his extracurricular activities, which included “filmmaking,” a very public relationship with his “director” Marlena and his outrageous pairing with the demented Luna Vachon.


#17 The Dudley Boyz

The 20 Icons of The Attitude Era

We’ve never been to Dudleyville, but if Bubba Ray & D-Von are any indication of its populace, we won’t be vacationing there anytime soon. With unnerving, faraway stares behind their taped, thick-rimmed glasses, the brothers from different mothers ventured from ECW in South Philadelphia to WWE in 2000. With the Dudleys came the savage, hardcore tendencies that made them the most dangerous tag team in The Land of the Extreme — namely their penchant for driving their opponents through tables.

Despite their heinous behavior, the take-no-prisoners duo would eventually become fan favorites, sending the WWE Universe to its feet in anticipation whenever Bubba would exclaim, “D-Von, get the tables!” The pine-splintering impact that followed would send crowds around the world into a frenzy.

Not long after debuting in WWE, the Dudleys found themselves at the center of a tag team renaissance in WWE, clashing with Edge & Christian and the Hardys in the first-ever Tables, Ladders & Chairs Match at SummerSlam 2000 and an explosive rematch at WrestleMania X-Seven.

#16 Bret “Hit Man” Hart

The 20 Icons of The Attitude Era

The landscape of WWE began to shift drastically in 1997 thanks to the bold actions of gritty, hard-edged Superstars like “Stone Cold” Steve Austin, and Bret “Hit Man” Hart was perhaps the most vocal critic of what the WWE Universe would come to know as The Attitude Era. Surprisingly, WWE Universe members continued to gravitate toward the irreverent Texas Rattlesnake and the flamboyant Shawn Michaels, a trend Hart viewed as an affront to his more traditional values.

“Hit Man’s” relationship with rebellious American crowds would continue to sour, as an aggravated Hart touted the ethical superiority of his Canadian countrymen over fans in the United States and around the world. Suddenly, the ring general once applauded for his technical abilities became notorious for his scathing commentaries on the loose morals of his fellow Superstars and the crowds that admired them. Hart’s frustration with WWE even prompted “Hit Man” to shove Mr. McMahon to the canvas during an in-ring confrontation on the March 17, 1997, edition of Raw — six months before a Stunner to The Chairman ignited the iconic Austin-McMahon rivalry.

As Hart vented to millions around the world on Monday Night Raw, The Excellence of Execution became the subject of controversy behind the scenes as news of his contract dispute with WWE and his impending jump to WCW came to light. This conflict would reach a boiling point at Survivor Series 1997, where a plot orchestrated by WWE Chairman Mr. McMahon ensured Hart would not leave Montreal with the WWE Title.


#15 Kurt Angle

The 20 Icons of The Attitude Era

After winning a gold medal at the 1996 Summer Olympics — with a broken neck, no less — celebrated amateur wrestler Kurt Angle would find his way to WWE in late 1999. Clad all in red, white and blue, Angle attributed his success to his “Three I’s” (intensity, integrity and intelligence), all the while lambasting members of the WWE Universe who did not live by his example.

Standing in stark contrast with The Attitude Era’s popular renegades like “Stone Cold” Steve Austin, D-Generation X and The Rock, the earnest, self-congratulatory “American hero” didn’t exactly connect with the WWE Universe at the time, but he excelled despite the disapproval of crowds around the world. Capturing both the European and Intercontinental Titles in February 2000 — making him a “EuroContinental Champion”— Angle went on to win the King of the Ring Tournament and the WWE Championship to round out one of the most impressive rookie years in WWE history. 

Though often not on purpose, Angle was frequently responsible for some of the most humorous moments of the time, including his association with Edge & Christian (as a member of “Team ECK”), strumming the ol’ guitar with Austin and his Texas Rattlesnake–esque milk truck assault on The Alliance in 2001.

#14 Team Xtreme

The 20 Icons of The Attitude Era

Few Superstars put their bodies and careers on the line during The Attitude Era quite like Matt & Jeff Hardy. Risk-takers who would do anything it took to reach the apex of WWE’s burgeoning tag team division, the six-time World Tag Team Champions continuously broke new ground during The Attitude Era (not to mention new tables, ladders and chairs).

Entering WWE under the tutelage of ring veteran “Fabulous Freebird” Michael “P.S.” Hayes, the Hardys combined a devil-may-care attitude with stunning aerial proficiency that put themselves firmly in the hunt for the World Tag Team Championship. The highfliers’ omnipresent desire for greatness put them at odds with Edge & Christian and The Dudley Boyz, with whom the pair had several innovative tag team collisions.

Rounding out Team Xtreme was the stunning and awe-inspiring Lita, a risk-taker in her own right who would use her kinetic high-flying arsenal to capture the Women’s Title an impressive four times.


#13 Stephanie McMahon

The 20 Icons of The Attitude Era

There are few power players of The Attitude Era quite like Stephanie McMahon, who transformed from doe-eyed ingénue to cold-hearted manipulator in the blink of an eye in December 1999 when she married Triple H to lay the foundation for The McMahon-Helmsley Regime. The group, comprised of D-Generation X and remnants of The Corporation, ran roughshod over WWE throughout much of 2000, targeting The Rock, Mick Foley, the Hardys, Kane and anyone else who opposed its rule.

With the help of her McMahon-Helmsley compatriots, “The Billion Dollar Princess” captured the Women’s Championship from Jacqueline on the March 28, 2000, edition of SmackDown. Lita would put an end to Stephanie’s title reign and the regime dissolved in late 2000, but Mr. McMahon’s only daughter never lost her thirst for absolute authority. Colluding with her brother Shane, Stephanie helped orchestrate yet another companywide takeover, forming a massive coalition of WCW and ECW competitors known as The Alliance.

Business savvy, a taste for power and a tendency to mix it up in the ring now and then? Well, you know what they say about apples and trees.


#12 Big Show

The 20 Icons of The Attitude Era

They say it’s all about first impressions, and few Superstars have introduced themselves to the WWE Universe quite like Big Show did during St. Valentine’s Day Massacre in 1999. Tearing through the ring canvas to attack “Stone Cold” Steve Austin during The Texas Rattlesnake’s Steel Cage Match with Mr. McMahon, the goliath shockingly tossed Austin into the side of the unforgiving cage with such force that the entire panel gave way, inadvertently granting “Stone Cold” a victory by freeing him from the structure.

Despite technically failing in his initial task to aid The Chairman, the former WCW World Heavyweight Champion was quick to earn a reputation as a near-unstoppable angry giant, performing such imposing feats as pulling down the TitanTron and chokeslamming The Undertaker through the ring to the arena floor. Any Superstar foolish enough to make things personal with Big Show — as The Big Bossman did by mocking the juggernaut’s deceased father — would pay dearly.

Despite being perceived as a monster throughout much of The Attitude Era, The World’s Largest Athlete displayed a penchant for entertaining the WWE Universe, lampooning WWE Legends and fellow Superstars with less-than-flattering imitations like “Showkishi,” “The Showster” and “The Big Showbowski.”


#11 Edge & Christian

The 20 Icons of The Attitude Era

Whether rolling with the vampiric Gangrel, racing to the ring through the crowd or holding classic five-second poses “for the benefit of those with flash photography,” Edge & Christian continuously reinvented themselves both inside and outside the ring.

But even if you take away Edge & Christian’s ridiculous(ly cool) sunglasses, pompous posedowns and their unique ability to “reek of awesomeness,” what you’re left with is one of the most technically sound tag teams to ever compete in WWE. Mixing mat-based proficiency and high-impact aerial attacks, the pair flourished in the intensely competitive tag team division during The Attitude Era, historically winning WWE’s first two Tables, Ladders & Chairs Matches at SummerSlam 2000 and WrestleMania X-Seven, respectively.


#10 Chris Jericho

The 20 Icons of The Attitude Era

With his flashy attire, irreverent demeanor and a complete lack of verbal restraint, WCW expat Chris Jericho fit right in when he debuted on Raw during the height of The Attitude Era on Aug. 9, 1999. Boldly interrupting The Rock (more on him later), The Ayatollah of Rock ‘n’ Rolla introduced himself as a “new hero” and the “party host” of the WWE Universe, even having the brass to call The Great One an “idiot.” Needless to say Y2J incurred the wrath of The Brahma Bull that night.

But Jericho’s ability to get under just about anyone’s skin made him stand out in an era defined by microphone masters, with Jericho laying waste to his opponents with acidic insults more than a decade before CM Punk dropped his first “pipe bomb.” Some of the worst recipients of Jericho’s rapier wit were Kurt Angle and Stephanie McMahon, who received a particularly unflattering and long-winded nickname from Y2J that we can’t publish here.

In the ring, Y2J was equally impressive, making WWE history by becoming the first-ever Undisputed Champion at Vengeance 2001 when he defeated both “Stone Cold” Steve Austin and The Rock in a single night.


#9 Kane

The 20 Icons of The Attitude Era

Through hellfire and brimstone, Kane made his explosive WWE debut at Badd Blood: In Your House in 1997, attacking his brother The Undertaker during the first-ever Hell in a Cell Match pitting The Phenom against Shawn Michaels. With that bold statement — which included tearing the door off the Cell itself — The Big Red Monster set the tone for his destructive WWE career.

Seeking retribution against Undertaker, who allegedly started a funeral home fire that left him physically and psychologically scarred, Kane would go on to lash out against the entire WWE roster. The unhinged psyche of The Devil’s Favorite Demon made him an immediate challenger for WWE’s most elite titles. In a memorable First Blood Match with “Stone Cold” Steve Austin at King of the Ring 1998, Kane captured his first-ever WWE Title.

The WWE Universe would soon learn Kane was far more than a demented monster, however, as Kane found allies in D-Generation X. The Big Red Monster struck up a bizarre kinship with the degenerate X-Pac, and the duo went on to win the World Tag Team Titles twice. Kane’s other bizarre and humorous Attitude Era team-ups included an alliance with the massive Rikishi, the super heroic Hurricane, the high-flying Rob Van Dam and even his estranged brother. 


#8 The New Age Outlaws

The 20 Icons of The Attitude Era

“Oh, you didn’t know?!” Thanks to the weekly in-ring proclamations by “Road Dogg” Jesse James and Billy Gunn, the WWE Universe was always well-informed during The Attitude Era. A former “roadie” and a “Smoking Gunn,” respectively, Road Dogg and Gunn reinvented themselves as the rough-and-tumble New Age Outlaws after joining forces on Shotgun Saturday Night in 1997.

The pair would gain notoriety after defeating Legion of Doom for the World Tag Team Titles on the Nov. 24, 1997, clinging to their titles by bending the rules in a manner befitting their “outlaws” moniker. It was this gleeful disregard for the rules that cemented The New Age Outlaws as the most influential tag team of The Attitude Era.

Not long after controversially and memorably locking Cactus Jack and Chainsaw Charlie in a dumpster and tossing it off the entrance ramp, The New Age Outlaws were welcomed into a new iteration of DX on March 30, 1998. This all-new DX roster — consisting of Gunn, Road Dogg, X-Pac and Triple H — brought a true sense of fun to Monday nights, hilariously lampooning rival factions such as The Nation of Domination and The Corporation. Perhaps The New Age Outlaws’ most memorable DX moment, though, was when the rebellious faction — equipped with an army tank — invaded WCW’s live Monday Nitro television broadcast and brought a new, literal meaning to “The Monday Night War.”


#7 The Undertaker

The 20 Icons of The Attitude Era

The Undertaker was already a two-time WWE Champion and undefeated at WrestleMania by the time The Attitude Era truly began picking up steam, but The Phenom would nevertheless continue breaking new ground throughout the late 1990s and early 2000s.

The Undertaker’s harrowing, wince-inducing Hell in a Cell Match with Mankind at King of the Ring 1998 quickly became the stuff of legend, and his sibling rivalry with Kane captivated the WWE Universe as the brothers battled in hellacious grudge matches, including the first-ever Inferno Match at WWE Unforgiven in 1998.

Not content with championship gold or other in-ring conquests, The Undertaker would make the ultimate power grab in 1999, when he formed The Ministry of Darkness and held Mr. McMahon’s daughter for ransom. The Phenom’s demand? Complete and total control of WWE. Although “Stone Cold” Steve Austin played countless mind games with The Chairman throughout The Attitude Era, The Undertaker truly hit Mr. McMahon where it hurt.

Speaking of hitting people where it hurt, The Undertaker would continue to dominate in the ring throughout The Attitude Era, with and without his Ministry. The Deadman would forge successful tandems with Big Show and even his brother, and would play an instrumental role in defending WWE from the WCW/ECW Alliance in 2001.


#6 Shawn Michaels

The 20 Icons of The Attitude Era

From forming the rebellious D-Generation X alongside Triple H to playing an (unwitting) role in the shocking incident at Survivor Series 1997 to his alignment with “Iron” Mike Tyson at WrestleMania XIV, Shawn Michaels’ proximity to controversy throughout the 1990s makes The Showstopper one of the founding fathers of The Attitude Era. And if you’re not down with that, we’ve got two words for ya …

Well actually, we’ve got a few more words than that. Although Michaels was absent during a sizable portion of the Attitude Era due to a debilitating back injury, the 2011 WWE Hall of Famer’s impact was felt throughout the years “Stone Cold” Steve Austin and The Rock were raising hell and eyebrows, respectively.

HBK’s over-the-top and brash persona paved the way for so many other Superstars prone to bucking the establishment, while his earlier high-flying collisions with the likes of Bret Hart and Razor Ramon set the bar high for an entirely new generation of risk-takers.


#5 Mr. McMahon

The 20 Icons of The Attitude Era

Not so fast, D-Generation X. WWE Chairman Mr. McMahon enthralled the WWE Universe during The Attitude Era with two words of his own:


Our fans were more than familiar with seeing and hearing Vince McMahon on WWE broadcasts — including Raw — but it was The Chairman’s storied rivalry with “Stone Cold” Steve Austin that made Mr. McMahon an unforgettable part of Monday nights. A devious authority figure that opposed the rebellious Texas Rattlesnake at every turn, Mr. McMahon was arguably just as crucial to Austin’s meteoric rise during The Attitude Era as the finger-gesturing, beer–guzzling, “Stone Cold” Stunning Superstar himself.

When he wasn’t lamenting the loss of his prized Corvette, wringing the beer out of his custom-made suits or putting ice on the bedpan welts on his head — all of which could be attributed to The Texas Rattlesnake — Mr. McMahon was focused on overseeing the ascent of his “Corporate Champion” The Rock (you might have heard of him), training for the 1999 Royal Rumble (which he won) and even winning the WWE Championship from his future son-in-law, Triple H.

Oh and remember how WCW’s Monday Nitro was trouncing Monday Night Raw in the 1990s? Mr. McMahon would celebrate a definitive victory over Ted Turner’s rival organization in March 2001, when WWE purchased WCW.


#4 Mick Foley

The 20 Icons of The Attitude Era

During The Attitude Era, you might have known him as the unhinged Mankind, the barbaric Cactus Jack or the tie-dyed lothario Dude Love. Today, however, we salute Mick Foley for his myriad contributions to sports-entertainment during the 1990s … and that doesn’t just include being able to withstand a 20-foot drop off Hell in a Cell at King of the Ring 1998.

Competing in legendary clashes with The Undertaker, Triple H and The Rock, “Mrs. Foley’s Baby Boy” utterly captivated the WWE Universe, overcoming seemingly insurmountable odds and putting his body on the line in an effort to fulfill his lifelong dream: to become WWE Champion. Foley would accomplish that lofty goal on the Jan. 4, 1999, edition of Raw.

On that night, Foley defeated The Rock to earn his first WWE Title — a victory he would later dedicate to his children. The occasion not only represented a personal triumph for The Hardcore Legend, but also a victory for WWE itself. On that night, WWE turned the tide in its longstanding battle with WCW’s Monday Nitro, doling out a debilitating ratings blow from which the Atlanta-based organization would never recover.

Outside the ring, Foley became a New York Times best-selling author with the 1999 release of his first autobiography, “Have a Nice Day: A Tale of Blood and Sweatsocks,” and was solely responsible for a surge in sock puppet popularity with the debut of his questionably odored ally, Mr. Socko.


#3 Triple H

The 20 Icons of The Attitude Era

Refined, ceremonial and just a tad bit obnoxious, “The Connecticut Blueblood” Hunter Hearst-Helmsley was utterly despised by the WWE Universe when he debuted in 1995, promoting the proper “etiquette” he honed growing up in posh Greenwich, Conn. Witnessing Helmsley parade himself down the entrance ramp to Handel’s “Hallelujah Chorus” in luxurious robes before arrogantly bowing in the ring, the WWE Universe could hardly imagine this pompous competitor would one day become synonymous with “Attitude.”

Embracing his inner rebel, Helmsley, now known simply as Triple H, joined up with his “Kliq” cohort Shawn Michaels to form D-Generation X — perhaps the most controversial faction in sports-entertainment history. After HBK left WWE due to injury in 1998, Triple H became DX’s leader, bringing X-Pac and The New Age Outlaws into the degenerate fold as the group caused chaos in WWE, raising the ire of Mr. McMahon and anyone else unfortunate enough to assume authority during WWE’s most rebellious era. Triple H even led a DX invasion against Monday Nitro, literally bringing “The Monday Night War” to the rival organization’s doorstep.

Triple H’s own aspirations would supplant his desire to rebel, however, as he would ultimately assume authority in WWE when he married Mr. McMahon’s daughter, Stephanie. With the formation of The McMahon-Helmsley Regime, The Game took ownership of the illustrious WWE Title throughout much of The Attitude Era, battling fellow icons like The Rock, Mankind, Chris Jericho and “Stone Cold” Steve Austin. In fact, it was Triple H who masterminded an automobile attack on The Texas Rattlesnake that took Austin out of action for a year. Cerebral Assassin, indeed.


#2 The Rock

The 20 Icons of The Attitude Era

Everyone smelled what The Rock was cooking during The Attitude Era. The grandson of “High Chief” Peter Maivia and the son of Rocky Johnson, The Rock was seemingly destined for in-ring greatness from birth … but few could have anticipated the heights “The Most Electrifying Man in All of Entertainment” would someday reach.

The smiling, tassel-wearing Rocky Maivia attracted a great deal of attention at Survivor Series 1996, where he was the sole survivor of his squad, and was applauded for his Intercontinental Championship victory over Triple H the following year. Despite his clean-cut appearance and positive outlook, it wasn’t until The Rock lashed out at the WWE Universe in frustration that crowds truly began to gravitate toward him.

It was that signature gift of gab that would not only cement The Rock as one of the most captivating in-ring performers in any era — Attitude or otherwise — but also a fixture in popular culture. The Brahma Bull’s clashes and begrudging partnership with Mankind as The Rock ‘N’ Sock Connection were endlessly entertaining, as was his persistent berating of Michael Cole, his affinity for fine lodging (the SmackDown Hotel, at the corner of Know Your Role Blvd. and Jabroni Drive) and his well-documented love of pie.


Pastries aside, The Rock wasn’t just a force on the mic, bringing to the ring unmatched intensity in classic bouts with “Stone Cold” Steve Austin, Triple H and even Hulk Hogan.


#1 “Stone Cold” Steve Austin

The 20 Icons of The Attitude Era

“Austin 3:16 says I just whooped your a**!”

With that proclamation at King of the Ring 1996, “Stone Cold” Steve Austin set into motion a veritable revolution that would forever change the face of sports-entertainment. At the center of that revolution over the next several years was The Texas Rattlesnake himself, whose clashes with authority and take-no-prisoners approach to, well, everything inspired an entire generation of Superstars to speak their minds and take charge — the very essence of The Attitude Era.

There was nothing complicated about Austin, whose true passions never seemed to extend beyond raising hell and a few celebratory cold ones to his lips. But what Austin lacked in flashy ring gear and theatrics he more than made up for in personality, which oozed from The Texas Rattlesnake like venom whenever he entered an arena. When the sound of breaking glass heralded the arrival of “Stone Cold,” the WWE Universe knew that, as Jim Ross would say, “business was about to pick up.”

When thinking back on The Attitude Era, “Stone Cold’s” frequent battles with Mr. McMahon immediately spring to mind, and for good reason. The Bionic Redneck’s ability to get under The Chairman’s skin kept WWE Universe members glued to their TV sets each and every week as we all waited to see what Austin would do or say next.

Whether he was driving down the entrance ramp in a Zamboni, dousing The Corporation with beer or battling the likes of Shawn Michaels, The Rock and Triple H for the WWE Title, “Stone Cold” personified what it meant to be a WWE Superstar during The Attitude Era … and that’s the bottom line.


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