10 Most Shocking Heel Turns In WWE

7. The Bearer Of Bad News

There was something not quite right about The Undertaker's original pairing with Brother Love, a fact that WWE seemed well aware of, as they soon switched him out for the much more appropriate figure of Paul Bearer. 

The ghastly duo were instantly iconic and fit like a pair of purple gloves. 

Under the guidance of Bearer, The Deadman flipped between heel and face and back again, achieving success as WWE Champion and quickly cementing himself as one of the company's strongest and most popular characters, regardless of whether he was a goody or a baddy. 

After five-plus years by each other's sides, a split in the summer of 1996 was not too surprising, but the manner in which it happened truly was. 

The turn took place at the end of Undertaker and Mankind's chaotic Boiler Room Brawl battle at SummerSlam, as they made their way into the arena and fought over possession of the mystical urn (you can't spell 'turn' with 'urn' after all). 

Bearer refused to hand it to his protege when he had the advantage and instead proceeded to help put the boots to the Phenom, switching allegiances to Mankind, much to the confusion of both 'Taker and the crowd in attendance.

There would be many more twists and turns in the Bearer/Undertaker relationship in the coming years, but this initial turn still ranks as one of the most shocking aspects of their storied association.