Number of kids: 10+

This list is as much a fucked-up tribute to father's on Father's Day as it is a PSA to wear a rubber or, if you don't have one, watch a movie or go out for ice cream or something. Seriously dude, consequences can await if you frequently feed into the desires of your ding dong. Enter: Jason Caffey, a Bulls reserve who won two rings and earned $29 million dollars on a pair of '90s Chicago teams. Not soon after his career dried up, so did the money. When the money dried up, the legal problems hit. When the legal problems hit, a judge dismissed his bankruptcy filing. When that happened, the mothers of his children (which at last count was eight) sought back child support that added up to several hundreds of thousands of dollars.