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You Spoony Bard
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Sharpshooter and Liontamer because they've both been applied to me when I was younger. They hurt like hell.
 

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Too many to mention as they all look like they hurt when you are younger surely?

As for now? Finn Balor jumping stomp from the top rope is insane. That's a rib breaker right there.
 
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Batista Bomb. Legit hurt, can tell you that.
 

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We need to be differentiating between physical hurt and work incompacitation. I'm fairly sure Yoko landing on one's chest was quite painful even when guarded against right. He was no small man.

A properly executed Jackknife powerbomb looks like it could damage the lower back in work. We've seen the effects of it used when it shouldn't be, and that's real hurt. Even pulled off to a T I'd be willing to bet it more than stings when making that mat contact.
 

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yokozuna banzai drop I just don't understand how that doesn't hurt..

Got to give some rep for Wrestlemania the arcade game.


To answer the question, The Razors Edge
 

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It wasn't a finishing maneuver but every time I saw Bad News Brown drive his knuckle into the throat of his opponent I would cover my throat and wince.

Also Sid's powerbomb. I legit cringed especially when the jobber leaned forward after impact with his face in pain before falling back onto the mat.
 

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The Fresh Prince Is Back On His Throne!
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The Boston crab, at first I thought it looked simple and it wouldn't hurt but then I had it applied to me. Seriously painful.
 

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I got speared into a tree once and it rly hurt
 

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When Jericho was doing the Liontamer on the small cruiserweights , it looked like he was litterally breaking them in half .
The other one would be the piledriver that Scott Steiner used to do , it looked like he killed the motherfucker .
 

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Getting molested by Bill DeMott
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I broke a classmates nose putting him in the crippler crossface from a standing position when I was younger. Not my proudest moment....
 

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Liontamer looks legitimately painful
 
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