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Britney Spears, Justin Timberlake
After making a big splash on the pop music scene with back-to-back hit albums …Baby One More Time and Oops! … I Did It Again, Spears and *NSYNC singer Justin Timberlake went public with their romance at the 2000 MTV Video Music Awards. They had a cute connection – they both appeared on “The All New Mickey Mouse Club” in the 1990s – and quickly became tabloid fodder as they dressed in matching outfits and had adorable pet names for one another. Their 2002 breakup (amid rumors she had cheated) apparently hit Spears hard. In the recent court case brought against the entertainer and her parents by her ex-manager Sam Lufti, an attorney for the Spears family said she was left depressed and angry from the split, which thrust her into a downward spiral.

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