4. Diesel (1996)
After his loss to Bret Hart in late 1995, Big Daddy Cool gained a new edge, but still walked the line between good guy and bad guy. By early 1996, however, there was no question that Diesel was a full-fledged heel, and a terrific one at that. In a situation very similar to Michaels' aforementioned heel turn, Big Daddy cool had spent the year prior to his turn as the company's number one babyface. Turns out, however, that Kevin Nash makes a better bad guy than a good guy. During the final months of his WWE tenure, Diesel engaged in some behavior that up until that point wrestling fans had never seen the likes of. He threw his leather jacket at Vince McMahon's face, and at a time when it had hardly been done before, he powerbombed his former best friend, Shawn Michaels, through the announcers' table. Nash may have left WWE in May of 1996, but his time as a top heel in wrestling was far from over. Upon arriving in WCW, Nash, along with good buddy Scott Hall, joined up with a certain someone else on this list to form arguably the greatest heel group in the history of professional wrestling.