4. Ashton Kutcher
Esquire magazine said that Ashton was once used as a front for the biggest sports betting syndicate in the US.
According to his public statements he said was earning as much as $750,000 in four weeks by betting on college football.
We have reasons to believe that he used to take 10% cut of those earnings. He was close to being charged with messenger betting, a practice that is illegal in the state of Nevada.
It seems that he was lucky, because no investigation was ever launched into his alleged activities.
He now enjoys his life next to Mila Kunis.