10 Most Toxic Hollywood Relationships Ever (2 of 6)

Miley Cyrus and Liam Hemsworth

Miley and Liam met on The Last Song and promptly turned their relationship into a multi-season soap opera. They dated, broke up, got back together, broke up again, got engaged, faced cheating rumors, split, reunited, and eventually married—all that only to divorce once more. By the time Miley dropped “Flowers,” we had a playlist and a timeline of their entire emotional journey.

Chris Brown and Rihanna

Chris Brown could have been his own category after all his bad relationships. He and Rihanna went from pop power couple to cautionary tale overnight. On the eve of the 2009 Grammys, a brutal argument left Rihanna visibly injured and the world horrified. Years passed. In 2012, Chris apologized, leading people to believe he had changed, and the two decided to give their relationship another chance. The second try did not last long, however, as they split up once again shortly after the reunion.