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#4 Stone Cold Steve Austin
When Stone Cold Steve Austin turned heel at WrestleMania X7, it was perhaps the most confusing heel turn of all time. Many in the arena thought Vince McMahon had turned face and throughout his run as a heel, fans simply didn't boo him.
When Stone Cold realized this, he relied a lot more on comedy, stating that he needed to entertain the fans in some way. This resulted in a lot of memorable comedic segments, particularly between him, Vince McMahon and Kurt Angle.
He would turn face soon after the Invasion Angle ended in 2001 and stay that way till his retirement.
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