#2: Owen pranks the Boss
Though he spent much of his career as a cowardly heel, when it came to pranking, Owen wasn't afraid of anyone, not even his own boss, Vince McMahon. After the boss booked a Hogpen match between Henry Godwinn and a young Triple H in 1995, Owen vowed to make the boss pay, though we're not quite sure what it had to do with him.
The day of the match, a large truck containing various barn animals arrived, and when the driver asked where the animals needed to go, Owen 'kindly' offered to show him the way. Instead of taking them, Owen directed the driver and his animals to Vince's office, whereas you can imagine, all hell broke loose. Leaving the boss' office a manure ridden tip, it's amazing that the Canadian wasn't punished for this.