10 DUMB WWE Heel Turns (We Didn't Want To Admit Were GENIUS!)
2. Steve Austin (2001)
Ask the man himself about it today, and Steve Austin will tell you he should've hit a kick, wham, stunner combo on Vince McMahon at WrestleMania X-Seven. 'Stone Cold' thought he needed a fresh wrinkle by April 2001, so he "shook hands with the devil" after beating The Rock in the 'Mania main event and turned heel for the first time since 1997.
That's roundly considered a mistake, but was it so bad? Austin's turn certainly fit the story the WWF had been telling since his late-2000 return. He grew desperate and wanted to reclaim top spot as World Champ again, and even told Rocky that he "needed" to beat him "more than anything else in the world".
The warnings were there.
Going heel let Austin explore other aspects of performance too. He dabbled with comedy (skits with McMahon, Debra and Kurt Angle were laugh out loud hilarious), and proceeded to experiment with the thought that he'd been losing his mind anyway. Cracks appeared in early-2001, then everything came to a head on the biggest show.
Austin's heel turn wasn't popular, but it was worth trying on.