Pro athletes and beautiful women go together like Based God and positivity. When you have young multimillionare men that people across the world adore for their talents in their respective sport, you're going to have groupies galore. Over the course of history there have undoubtedly been athletes who've taken the sports stary lifestyle to a whole new level. You've got the legends in the game like Wilt Chamberlain and James Hunt who did it pre-Twitter, new school guys like Mario Balotelli and J.R. Smith who show little regard for anything outside of having a good time, and of course you got your vets who've slowly built up their stat line in Derek Jeter and Cristiano Ronaldo. In honor of Wilt Chamberlian's birthday, here are the 20 Biggest Playboys in Sports History.