#1. WWE Hall of Famer 'Stone Cold' Steve Austin: Unhappy and regretful over his heel turn in WWE in 2001
It's believed that WWE's famous Attitude Era began at WrestleMania 14 in 1998, and concluded at WrestleMania X7 in 2001. The golden period began with 'Stone Cold' Steve Austin winning the WWE Championship, and it ended with the same result, but under different circumstances.
By 2001, 'Stone Cold' Steve Austin was bar none the hottest babyface in WWE. Both he and The Rock were megastars of their era, and despite his popularity, Austin feared that his babyface run was on the verge of getting stale.
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This resulted in the infamous WrestleMania X7 moment where Steve Austin turned heel during his match against The Rock in the main event. After winning the WWE title back, he shook Vince McMahon's hand - a moment that was supposed to be shocking.
However, what it actually led to was a lot of confusion. Austin quickly understood that he was wrong about his character getting stale. Nobody wanted to boo him, and even when looking back at the match, Austin was cheered heavily upon his victory.
Speaking to Chris Jericho on the Talk is Jericho podcast, Austin revealed that he quickly regretted the decision for him to turn heel:
“When I turned heel after WrestleMania 17 and I wish I would’ve never done it and I wish I would’ve called an audible but I was a heel. When I commit to something, I am in so I’m gonna go to the end of the world – even though nobody wants to hate me, I’m kinda John Wayne of the wrestling world. But I was gonna do everything I could to make you hate me. So I was committed to doing that,” said Austin. (H/T Inside The Ropes)
Ultimately, Austin transitioned from being an intense heel to a more comedic one, as he went on to have some iconic comedy skits with Kurt Angle, Vince McMahon, and many other superstars.
Austin revealed that the reason why he took a comedic heel approach was the fact that his initial heel turn didn't work, so he felt the need to be an entertaining bad guy.