#5 Ric Flair (2006)
The Nature Boy has done it all in the wrestling business. An astonishingly long and stellar career has made him the first ever two-time WWE Hall Of Famer. Ric Flair has done some pretty memorable things as part of the WWE, including his classic Royal Rumble 1992 performance, being part of Evolution, and completing the WWE triple crown by winning the Intercontinental Championship.
However, it is a surprising fact that Flair has also competed in a Money in the Bank ladder match. 57 years old at the time, Flair was part of the second ever Money in the Bank match at Wrestlemania 22 in 2006. He took a crazy bump when he was SUPLEXED from the top of the ladder, an unbelievable and unnecessary risk taken at his age. He still returned to try and win the briefcase later in the match, but was unsuccessful.
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Here's hoping that his daughter, Charlotte has more luck in this type of match in the future, as she is one of eight women to compete in the second ever women's Money in the Bank ladder match on June 17th.
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