1. Vince McMahon announces the Attitude Era, 1997
Mr. McMahon kicked off one of the WWE’s most iconic eras with the force of a steel-toed boot to the head, announcing violence, cursing, and beer-swilling anti-heroes in the stead of the circuit’s formerly family friendly vibe. It was the end of an age, and the beginning of a revolution.
2. “The Montreal Screwjob” at the Survivor Series, 1997
Undoubtedly the Attitude Era’s most controversial moment, this infamous bout is largely thought to be a rare intersection of real-life and on-screen drama. Tensions were already tangible between on- and off-screen rivals Shawn Michaels and Bret Hart, but when the dastardly Mr. McMahon ordered the match cut short and the Championship awarded to Michaels, the strife between the two skyrocketed and the match’s notoriety was sealed.
3. The Undertaker’s brother, Kane, makes his debut at In Your House: Bad Blood, 1997
Fans had been restlessly anticipating the wrestling debut of the Undertaker’s long-lost brother, but nobody could’ve prepared themselves for when the real-deal was revealed. The masked Kane swaggered into his half-brother’s Hell in a Cell match, and in a flurry of fireworks, felled the Taker with his own signature move.
4. Steve Austin packs heat against Vince McMahon on RAW, 1998
When the Texas Rattlesnake pulled a pistol on his nefarious nemesis — live on TV, no less — it wasn’t so much a stunt as a proclamation: the black-and-white good guys and bad guys of yesteryear are no more. Antihero Steve Austin was at the fore of this bold new era; a bona fide badass that effortlessly straddled the line between heel and face.
5. The Undertaker kidnaps and almost marries Stephanie McMahon on RAW, 1999
Sure, the Attitude Era got a little soap-y every now and then, but theatrical drama bombs like the almost-wedding between the Undertaker and Stephanie McMahon still glued an entire nation to their TV screens.
6. Mick “Mankind” Foley wins the WWE Championship at RAW, 1999
Of all the wrestlers that rocked and socked the WWE’s Attitude Era, it was scraggly superstar Mick Foley and his bevy of split personalities that may have most often entranced and entertained audiences. When the portly, masked performer’s most manic personality claimed the WWE Championship, it was a landmark moment in Foley’s decades-spanning career.
7. The return of Cactus Jack on RAW, 2000
And speaking of Foley, few of the portly pugilist’s stunts shook audiences more than this pre-match transformation into the Hardcore Legend’s most savage personality: the devilish Cactus Jack. It was worth it just to see the look on competitor Triple H’s face.
8. Mike Tyson and Steve Austin duke it out on RAW, 1998
It takes some serious brass balls to sass the “Meanest Man on the Planet” in front of a live arena audience, but if there’s one thing Stone Cold Steve Austin is lacking in, it sure as hell isn’t audacity.
9. Triple H crashes Stephanie McMahon’s wedding on RAW, 1999
The heiress to the McMahon dynasty may have narrowly ducked trading vows with the Undertaker, but heel supreme Triple H was the one that swooped in and sealed the deal, for better or for worse. Interrupting McMahon’s in-ring ceremony with his trademark ‘tude, the Game let it slip that he’d wed the Billionaire Princess with a quickie wedding in Las Vegas the week before. Mr. McMahon was less than thrilled.
10. WWE acquires WCW on RAW, 2001
Professional wrestling fans had long been split between the feuding WWF and WCW, but when prodigal son Shane McMahon made an unannounced appearance on Monday Nitro — announcing ownership of both factions — it was the eye-popping end to the circuit’s most chaotic, cruelest, and coolest era, and the beginning of an Invasion.