29. Michael Phelps
The most successful Olympian of all-time, Phelps is a United States icon. His 18 gold medals are a world record and he was a consummate professional throughout his swimming career. Apart from the time he lost several sponsors after pictures emerged of him smoking a bong, of course. That was the first hint that Phelps likes to embrace his dark side sometimes but it’s not the only time.
After his retirement, Phelps hosted a massive party in Las Vegas, Nevada, where hundreds of people were in attendance. These included friends, family, as well as a host of celebrities. There was a giant pool, lots of expensive alcohol, and dozens of bikini-clad women. Phelps pulled out all of the stops. Meanwhile, he allegedly won $100,000 playing blackjack that night.