22. Britney Spears and Justin Timberlake at the American Music Awards in 2001
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Britney Spears and Justin Timberlake first met when they were 10 or 11 years old but when Timberlake toured with his band NSYNC and Britney opened, sparks flew and they dated from 1998-2002.
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In 2001, they hit the American Music Awards together in this…memorable matching denim outfit. I think it speaks for itself why this one will always be on this list.
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