2.“Stone Cold” Steve Austin: WrestleMania 17
The next heel turn on this list is arguably the most stunning conclusion in WrestleMania history, while also standing as one of the most shocking heel turns in WWE. It involved “Stone Cold” Steve Austin at WrestleMania 17, toward the end of the main event bout against The Rock for the WWE Championship.
As the match escalated in brutality during a ferocious No Disqualification bout, Austin grew increasingly desperate. Just as his longtime enemy Vince McMahon arrived ringside, McMahon, rather than attacking Austin, handed him a chair that Austin would then use to throttle The Rock with, leading to his win. Following his victory, Austin shook hands with the now former CEO, in what was described by fans as “shaking hands with the devil himself.”
This heel turn was so shocking because for the better part of four years, Austin and McMahon had been engaged in a violent, bitter feud that defined the Attitude Era. Houston fans were desperate to see their hometown hero, Austin, win the WWE Championship, and to see him transform into a villain and align with McMahon was the ultimate gut punch.
While many fans debate the long-term success of having the “Texas Rattlesnake” as a heel because fans didn’t want to boo him, the moment of Austin teaming up with McMahon is the wrestling equivalent of Batman aligning with the Joker.