#1 David Flair
The career of the Nature Boy Ric Flair is the stuff of legend. From surviving a Plane crash, to winning 16 World Championships, the Nature Boy has risen past superstardom and is the only 2-time inductee into the WWE Hall of Fame.
So when his son David debuted in WCW in 1999, fans had high expectations. However, a confusing and pointless heel turn against his father left fans wanting to see less of the son of the Nature Boy. Trying to emulate his father, the younger-Flair wore robes and was awarded the US Title.
In WWE, Flair is best known for being a punching bag for the Undertaker in 2002, with his sister Charlotte being the much more successful of the two, with eight championships to her name, since making her in-ring debut in 2013.