Britney Spears didn’t just become America’s pop princess in the late ’90s — she also became half of the most-watched teen couple on the planet. Her romance with Justin Timberlake was pure TRL gold: matching denim at the 2001 AMAs, sugary PDA, and then heartbreak that fueled his megahit “Cry Me a River.
Speculation swirled that Britney had cheated, and though she stayed quiet at the time, her 2023 memoir later confirmed she strayed — with choreographer Wade Robson. Justin eventually apologized in 2021 for how he handled the breakup, but not before he milked the drama for his career.
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