Britney Spears' Love Life

Justin Timberlake (1998-2002)

They seemed like a match made in Mickey Mouse Club heaven, but when Justin Timberlake and Britney Spears decided to pull the plug on their picture-perfect Hollywood relationship in 2002 after four years of dating, things didn't quite end on a sweet note. Timberlake would go on to write his hit "Cry Me a River," reportedly about Spears' infidelity, and the pair would drift apart over the years.

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