1. Losing The 21 Year Streak To Brock Lesnar At WrestleMania 30
This was by far the most shocking WTF moment in The Undertaker's WWE career. Few ever imagined that he'd ever lose his 21 year WrestleMania undefeated streak. It had became so associated with his character and legacy. But then on April 6, 2014, the unthinkable happened. In New Orleans, at WrestleMania 30, Brock Lesnar pinned The Undertaker. Clean. The reaction of the crowd was stunned silence, followed by confused murmuring. The looks on peoples faces said it all - what the f**k!
