6. The Celebrity Gambling Ring with Your Stars Ben Affleck, Tobey Maguire & More. Talk about awkward times for celebrities! 2011 made life pretty horrible for Ben Affleck, Tobey Maguire, Matt Damon and a host of other stars when they were all sued for participating in an illegal gambling ring. Apparently it was quite the game of no-limit Texas Hold'Em with celebs acquiring huge amounts of debt. Ben denied the whole thing and especially the fact that he had lost $400,000 in the gambling ring. The whole thing caused quite the scandal. No we have to wait and see if any of the stars will come out and say if it's true. Obviously they'll all say it's false, so where's the fun in that?