#4 Paul Bearer turns on the Undertaker (1996)

When the Undertaker debuted in 1990 for the WWE, he was initially managed by Brother Love. Fortunately, this arrangement didn't last long, and Undertaker would be assigned a new, far more apropos manager; Paul Bearer.
By coincidence, Bearer had actually worked as a mortician before joining sports entertainment. His chilling appearance, creepy delivery, and full dedication to his character made him a great companion to Undertaker's monolithic presence.
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For six years, Undertaker and Paul Bearer were inseparable. That all changed in the shocking moment from SummerSlam 1996. During the infamous Boiler Room Brawl against Mankind, Paul Bearer would turn on his long time ally and aid Mankind in getting the victory.
No one in the WWE has a better win/loss record against the Undertaker than Mick Foley, and Paul Bearer is a big reason for that.