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Britney and Justin spent their childhood together while working on The Mickey Mouse Club and both went on to become pop sensations. They began dating in 1999 though didn't officially confirm the relationship until a year later. In 2002, they parted ways amid rumors of infidelity on Britney's side (Wade f*cking Robson, seriously?), leaving us with multiple cryptic breakup songs and one of the most iconic red carpet fashion moments of the decade.