10 Most Painful-Looking Wrestling Matches Ever

2. Shawn Michaels Vs. Stone Cold Steve Austin - WWF WrestleMania XIV

Aja Kong
WWE Network

Think about how much of a prize ar*ehole Shawn Michaels was at the dawn of the Attitude Era.

This was a man who thought nothing of destroying career after career; in fact, he laughed about it with his Kliq buddies, and turned into an even uglier person when he was without them at the midpoint of 1996. He completely derailed plans to return the biggest favour ever paid to him by a fellow professional by refusing to drop the WWF Heavyweight Title back to Bret Hart at WrestleMania 13, while having the audacity also to seek sympathy. He had lost his smile. Most would have been happy to see it wiped off his face, were it actually. It wasn't. He cried crocodile tears.

And still, equipped with that knowledge, one couldn't watch his belated Title loss to Steve Austin at WrestleMania XIV without a degree of the empathy Michaels himself once lacked entirely. His back mangled following the Royal Rumble '98 casket bump once thought to have ended his career, he fought through searing pain to wrestle a match that by his standards was somewhat subpar. It was still very good, but it was more than that: it was a karmic rebalance in which he endured physical agony as penance for the psychological warfare he had waged against the locker room. Just look at that propulsive, thunderous bump in the above GIF, knowing the state his back was in.

If you don't wince, you're either inhuman, or Bret Hart.

Contributor
Contributor

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!