10. Mike Tyson - $3.5 Million For WrestleMania 14
It isn't just wrestlers Vince McMahon has splashed out on, he's also spent significantly on non-competitive performers. Just months after telling Bret Hart he couldn't afford $1.5 million a year, McMahon went out and offered controversial boxer Mike Tyson $3.5 million for a role at WrestleMania 14. It would also involve a couple of Raw dates and a few promotional appearances, but it was pretty much money for the one big Mania date. Tyson ended up refereeing the main event between Shawn Michaels and Stone Cold Steve Austin. The investment paid off for McMahon, as Tyson's involvement put a lot of attention the WWF's way. The boxer's appearances are credited with being a big turning point in the WCW / WWF ratings war.