#4 David Flair

Though his sister Charlotte has had an objectively much more successful career, it was David Flair who was the first child of the legendary Nature Boy to enter the squared circle. As part of WCW, David would constantly be in his father's shadow, and even feuded with the Dirtiest Player in the Game at one point in his tenure. To his credit, David is a former WCW US Champion.
After a stint in WCW, Flair would eventually make his way to the WWE, though would only have a handful of appearances. After The Undertaker entered a feud with David's father, the heel Deadman made things personal by beating down the younger Flair, and would similarly eviscerate him in a match on the March 14, 2002 edition of SmackDown, just three days before the Deadman would give a similar beating to Ric at WrestleMania 18.
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His final match in 2008 saw him team with his younger brother, Reid Flair in a tag team match against the legendary Nasty Boys in what was actually Reid's in-ring debut as a performer, and David hung up his boots for good aged 29.