#2 Bischoff challenges Vince
Eric Bischoff was one of the shrewdest promoters in all of wrestling, second only to Vince McMahon. During the peak of the Attitude Era, Bischoff came out on an episode of Nitro and challenged Vince McMahon to a match at the upcoming PPV, Slamboree.
The match was heavily publicized, with a WCW security officer showing a picture of McMahon to the fans during the PPV, asking whether they had seen the man! A separate dressing room was made for Vince in case he did show up.
Eventually, Vince made the right decision and didn't show up to answer Bischoff's challenge. If Vince had shown up to fight, this would have resulted in a huge rating boost for WCW, no matter who won. It would probably have resulted in the demise of WWE. Bischoff was awarded the match after Vince failed to show up, and he bragged about the "win" for days to come.