7 Most Heartless Celebrity Breakups - Page 5 of 9

Rihanna and Chris Brown

This brutal, abusive relationship has been discussed over and over again, but it will never be okay to forget it. Right before the 2009 Grammy ceremony, Chris Brown, in a fit of jealousy, beat his girlfriend of two years, Rihanna, right in the car. The singer screamed, called for help, tried to escape, but Chris hit her in the face, head and then started choking her. Rihanna ended up in a hospital and filed a lawsuit against Chris. As a result, Brown was sentenced to six months of community service and a suspended sentence of five years.