4. Tobey Maguire
Unlike other celebrities, Maguire has prospered greatly as a poker player for which he is popularly known for. However, he acquired all his wealth in underground games organized by Poker Princess, Molly Boom. He was coached by the Canadian poker legend Daniel Negreanu. He has earned millions in winnings but he can be an ass despite winning these Hollywood high-stakes games. Sometimes, a host is forced to beg for a tip from his winnings.