When: 2008 – Present

Chris Brown and Rihanna were pretty much royalty as far as popular culture was concerned when they took their romance public in 2008. However, the fairytale union came to an abrupt ending when Brown roughed up Rihanna on the way back from Clive Davis’ pre-Grammy celebration in February 2009. Have no fear, though. An opportunistic Drake was there to pick up the pieces and offered a shoulder for Rihanna to cry on. The rumor is Drizzy and Rih hooked up, but neither have spoken explicitly about their history together.

Just when you thought the saga was over, the drama picked back up, only this time subliminal shots were taken in the form of song verses and subtweets. Simpin’ ain’t easy, but someone’s gotta do it.