#9. Bobby Brown
Bobby Brown lost his daughter, Bobbi Kristina Brown, just three years after the tragic loss of his first wife and long-time lover, Whitney Houston. Mimicking the fatal overdose of her famed and troubled mother, Bobbi Kris was found unresponsive in a bathtub in January 2015. In a medically-induced coma, she was reported to be brain dead before they pulled the plug on her in June of the same year at the age of 22.