#2 WWE legend The Undertaker
When The Undertaker first debuted his American Badass persona in WWE at Judgment Day 2000, it took some fans a while to get used to. His new look and presentation was a stark contrast to the Deadman character that had been haunting WWE for the last ten years at the time.
If you were having trouble processing the Undertaker’s new look at the time, his choice of ring gear for the 2000 Survivor Series certainly didn't help matters.
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The Undertaker was scheduled to challenge Kurt Angle for the WWE Championship.
Urban legend has it that the airport lost some of The Undertaker’s luggage, including the usual black leather pants that he would wear in the ring. So on the night of Survivor Series, The Undertaker had to borrow a pair from his good friend The Godfather. This would explain the striking snakeskin pattern that was definitely not a design choice usually akin to the Phenom.
Thankfully, The Undertaker wore these pants for one time only at Survivor Series 2000 and never after.