10. Usher & Chilli
We know this couple does sound a little dated, but their break up story is still epic, and one of the most controversial ever in the music biz! In 2003, word around the industry began to spread that the R&B couple were splitting after a radio interview where Chilli told the disc jockey that Usher did something that she could just not forgive. The interview left everyone wanting answers to what he could have possibly done, and bam! The 2004, diamond-selling album, Confessions dropped, revealing that Usher supposedly got another woman pregnant while the two were together, making their break up one of the most soap opera-like break ups of all time. Unfortunately, it was revealed years later that the narrative of Usher impregnating another woman was false and the album was actually based on Jermaine Dupri‘s actions. In reality, Chilli and Usher had just grown apart but not before tricking the world into thinking that Usher was a sleaze ball.
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