8. Missing Out On WrestleMania 2000
The Undertaker missed out on WrestleMania 2000 due to injury. That was a real shame for him, as it was the biggest WWF PPV in history at the time and would have handed him a huge pay day. But it isn't just the money that was a missed opportunity, it was also losing out at competing in an event that represented the WWF's peak. Yes, there have been bigger buyrates since, but Mania 2000 was really the peak of the late 90's wrestling boom. It was a legacy opportunity to work at a moment in time when the WWF was at unprecedented heights of mainstream popularity. It was 'cool' and the event transcended the usual Mania buzz.