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18. 2002: Britney Spears & Justin Timberlake
Let's all take a deep breath before we drive down this memory lane. The two met as tweens on The Mickey Mouse Club and officially started dating in 1999. Their relationship came to an abrupt end in 2002 and Timberlake released his video for "Cry Me A River" not long after, hinting that Spears had been unfaithful to him.