10 Wrestlers So Good They Changed Vince McMahon's Mind

5. Shawn Michaels

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"That little son of a bitch? He'll never be a babyface in this company! Never bring that idea up again!"

As recounted by Bruce Prichard to Sam Roberts, Vince McMahon saw Shawn Michaels only as a cocky midcard heel.

Vince McMahon wasn't wrong, exactly; in 1996, following the realisation of the Boyhood Dream, Michaels struggled to play the role of top babyface with the grit required to get over with the hyper-masculine crowd. His work was spectacular. Rich. But his peacocking personality - "the stripper he must have been in a previous life," as Bret Hart wrote in his autobiography - repelled the MSG tastemakers, who booed him out of the building at Survivor Series. He was a natural heel. Being a little sh*t simply radiated from him.

Happily, Shawn badly injured his back, and missed the four most lucrative years in North American wrestling history, the pathos of which informed the emotion of his 2002 babyface comeback. Michaels evolved from brat-pack pill-head to grizzled babyface across the two chapters of his career. He looked like a warrior overcoming his wrecked back, which he sold impeccably. On a far smaller scale, Shawn's psychological brilliance echoed Steve Austin's WrestleMania 13 breakthrough.

It was impossible not to respect such badass endeavour.

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Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!