9. Tom Brady
Famous (alleged) WAGs: Gisele Bundchen, Bridget Moynahan, Tara Reid
Another example of somebody just winning at life, Tom Brady does his thing on and off the field to the tune of a blackbook boasting actresses and models. We all know about his current ride or die wife Brazilian model Gisele Bundchen, but some forget his past relationship with baby mommma Bridget Moynahan and rumors of a fling with Tara Reid. Could Tom Brady partly be the cause of the Tara Reid trainwreck once he dumped her?