#6 Mankind
Already an international star under the name Cactus Jack Manson, Mick Foley arrived in the WWE during the start of the Monday Night Wars. Initially, he was pushed as a heel and was allowed to have multiple, clean wins over no less than the Undertaker. This decision was made by management not only to get Foley over, but to 'humanize' the Undertaker, who had been billed as unstoppable.
The two men engaged in a number of contests, such as the first Boiler Room brawl, and the second Hell in a Cell. It was during the Hell in a Cell match that Foley showed his willingness to take the sickest of bumps.
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Mankind would eventually turn face, and feud with the Corporation for the WWE world championship.
Why does Mankind make the list, when he was only around for a few years before Foley retired the gimmick? Simply put, Mankind WON the Monday Night War for Vince McMahon, with an assist from Eric Bischoff's arrogance.
Since Raw was taped at the time, and Nitro was live, Eric Bischoff would often give out the results of their rival show. He once spoiled Shawn Michaels's WWE championship win by saying 'he beats the big guy (Sid Justice) with three superkicks.'
Later, Mankind won the WWE Championship on Raw. Gleefully, Eric Bischoff told the television audience they didn't need to flip over to the other show, since "Cactus Jack is going to win the world title. Yeah, THAT will put asses in seats!"
Bischoff severely underestimated how much wrestling fans loved, Mick Foley. In droves, they tuned into Raw to watch their hero capture the title, resulting in a ratings victory for the WWE. The momentum continued, and it was the beginning of WCW's doom.
Here's the moment that changed the course of the war: