The Undertaker's 9 Weirdest WWE Rivalries

8. Vince McMahon

Vince McMahon's primary rivalry in WWE was of course with Stone Cold Steve Austin but his time with The Undertaker doesn't rank too far behind. As The Ministry of Darkness became bigger and badder in the late 1990s, The Undertaker set his sights on Vince as he looked to take control of the whole WWE. Taker would compete in an inferno match on Raw and have a small box delivered to McMahon where inside was a teddy bear. Vince, who was on commentary, would become very emotional at the sight of the bear before Taker set it on fire. During that same period, The Undertaker kidnapped Stephanie McMahon and planned to wed her in an €œUnholy Ceremony.€ Taker had her mounted on his 'T' symbol in the ring as the ceremony started before Stone Cold, of all people, came to her aid. This angle started to get a bit weird in the aftermath of the kidnapping. The Undertaker did this to torment Vince, or so it seemed€”but later it was revealed that he and Vince had been in cahoots the entire time. Stephanie and her mother Linda sided with Vince's nemesis Austin, and Vince responded by having the Undertaker kidnap Stephanie a second time. It's a wonder social services weren't called.
Content Producer
Content Producer

Video & written Content Producer for WhatCulture Wrestling. NCTJ trained journalist. BA Hons, Sports Journalism.