#1. X-Pac tears his anus
There is not better or nicer way to put it. While working a Jerry Lynn tribute show, X-Pac went to hit his signature Bronco Buster but after his opponent moved out of the way X-Pac slammed into the turnbuckle. It was a simple spot he had done thousands of times before and nothing had ever gone wrong.
X-Pac didn't notice anything until he finished the match and went back to the locker room. He had a huge puddle of blood in his singlet. He was taken to hospital in an ambulance. It turned out that he had torn his anus and required emergency sphincteroplasty.
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This is probably the weirdest injury that will ever happen to a wrestler. You know that when you have to question how somebody could even do something like that or if its even possible, that it is really unusual. X-Pac has said himself that there was no serious damage caused by the injury.