#4 The time he choked out Kurt Angle
Now, this is a story narrated by Kurt Angle himself in his autobiography It’s True, It’s True and is said to have happened on a plane from Europe back to the US after a tour. Angle apparently liked to constantly assert himself as the toughest guy in the locker room, with good reason perhaps, since he did win an Olympic Gold Medal with a broken freakin' neck!
On the plane ride, in a conversation with Angle, Vince McMahon apparently jokingly pointed out that he had once taken Kurt Angle down, which led to Angle jumping the boss and pinning him to the ground, all in jest. While the rest of the people on the plane that whatever was happening was not serious, The Undertaker was asleep and woke up with a start due to the commotion.
As soon as he woke up, seeing his boss being pinned down by Angle, The Deadman apparently got a hold of the Olympic Gold Medallist and choked him unconscious! Once it became clear that the whole thing was just a misunderstanding, he is said to have apologised to Angle, who took the whole incident sportingly.