8. The Undertaker vs The Big Bossman
https://www.youtube.com/watch?v=bJH-_uhC6Wk Going into 1999, the Undertaker had transformed from loveable caretaker of the dark world to satanic minister. He has re-aligned with Paul Bearer and after jumping through Vince McMahon's hoops in attempt to become WWF Champion, had settled in early 1999 to lead his Corporate Ministry. He vowed vengeance on Vince McMahon for all that he had done and set out to take the company from him. Going into Wrestlemania XV, Vince non-chalantly set up the Undertaker against Corporate-team member The Big Bossman in a Hell in a Cell match. While Bossman had been a serviceable heel for a time, he was nowhere near Undertaker's league. Even in a time where The Streak wasn't what it was, no one thought Bossman had a chance. Add on the Hell in a Cell and it made the match-up worse. Previous Cell matches featured barbaric action the likes fans had never seen before. The match was a snoozer. The buildup was all on Vince vs Undertaker rather than Bossman so the fans didn't care. It stayed in the cage and lasted under ten minutes. Undertaker won and then summoned the Brood from above. They lowered a noose into the cage and mock-hanged the Bossman from the cell as is raised back up. The image of Bossman hanging was widely pandered and the match was quickly forgotten from memory.