42. Britney Spears
Cheater: Kevin Federline
Date Of Affair: April 2004 - November 7, 2006
Years of Britney Spears' erratic behavior has maybe caused some to forget that she came between male dancer Kevin Federline and his girl Shar Jackson, formerly of the TV show Moesha, who just so happened to be expecting the LFO prancer's second child at the time he and Brit basically went nuts for each other. OK, maybe not, you all remember that shit. Yup, the ample-bottomed pop singer responded to critics by covering Bobby Brown's F-U anthem, "My Prerogative." This is all before we found out how crazy homegirl really, really was.