10 Worst Heel Turns In WWE History

5. The Undertaker (2001)

The Undertaker's November 2001 was one of the worst kinds in that it came completely out of nowhere. There was nothing preceding the turn that suggested The American Badass may be in for a change in character. He just up and appeared in the squared circle one night, interrupting Vince McMahon's induction of lead commentator Jim Ross in to the "Kiss My Ass" club. He did not, to the surprise of the Oklahoma fans, come to the aid of WWE's lead announcer. Instead, he went on a rant about respect and how he felt as though he had been denied it by fans, commentators and his fellow WWE superstars. In a sickening display, Undertaker forced good ol' J.R.'s face into the rear end of the Chairman of the Board, completing a most unexpected heel turn. Undertaker as a heel never really worked. He had built such a strong fan base for himself that even in feuds with The Rock and Ric Flair where he was doing things so totally despicable that one would assume he would generate jeers, major pockets of the audience still cheered him on. He was cool, an undeniable badass. At a time when Steve Austin was still recovering from his own ill-fated heel turn and The Rock had one foot out the door, Undertaker was an Attitude Era mainstay that they still had a strong belief in, regardless of whether he represented good or (Big) evil.
Contributor
Contributor

Erik Beaston is a freelance pro wrestling writer who likes long walks in the park, dandelions and has not quite figured out that this introduction is not for Match.com. He resides in Parts Unknown, where he hosts weekly cookouts with Kane, The Ultimate Warrior, Papa Shango and The Boogeyman. Be jealous.