Single… Again: Hip-Hop And R&B’s 10 Messiest Breakups


The Hook Up: After meeting at the Soul Train Music Awards in April 1989, Brown and Houston dated for several years before settling down together in July 1992.

The Break Up: Their tumultuous relationship featured claims of spousal abuse and drug abuse and Houston filed for a legal separation in September 2006 before filing for divorce just one month later. The couple was officially divorced in April 2007.

The Mess They Left: If Bobby and Whitney couldn’t survive together, what R&B couple possibly could?!