Chilli

Even though everything looked peachy-keen from the outside, Chilli and Usher were going through some hard times. Needless to say it shocked everyone when they split up in 2004. "He portrayed himself as faithful, and he wasn't," she told People. "I could never be with him ever again." We really thought this R&B couple was a match made in music heaven, but we knew it was over for real when Usher debuted Confessions and spilled all his dirty little secrets.

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