#1 Randy Orton
One of the most jaw-dropping moments that blurred kayfabe and reality in recent times in WWE was the match between Randy Orton and Brock Lesnar at SummerSlam 2016. The brutal match saw Lesnar landing vicious elbows to Orton's head, which busted him open.
The very graphic image of a bloodied Orton was a surprise considering how WWE had moved away from blood and gore. The Legend Killer revealed in an interview that he was happy with the outcome of the match and how much "buzz" it created, but was unhappy at how he suffered a concussion.
"I think with Lesnar, it’s always going to be him coming in every few months as a monster who destroys guys who work 200 days a year. There is a tendency for that to get old. I could have looked a little better that night and that would have helped me a lot regardless of the finish and not hurt Brock’s character at all. But the fact that you’re asking me about it three-four months later, means we created a buzz. But the fact that I had a concussion and was out for three weeks and wasn’t able to do anything pissed me off."
Randy Orton also showed his displeasure a year after that match when he retweeted a tweet mocking Lesnar, showing that he was still not over how brutal that match was.
There was a huge uproar backstage after the match as well, as Chris Jericho was worried about the health of his friend, Randy Orton, and Jericho and Lesnar butted heads after The Beast came backstage.