Chris Brown and Rihanna
Chris and Rihanna already had a horrible breakup in 2009 when Chris attacked Rihanna, but the dysfunctional decided to give their love another chance last year after Chris dumped Karrueche Tran to be with Rihanna. However, Chris and Rihanna ended up breaking up again earlier this year as Rihanna blasted Chris several times on Twitter and Instagram.