Question
Nsync star JUSTIN TIMBERLAKE in 2002

Which singer is Justin Timberlake's "Cry Me a River" about?

Last updated: January 11, 2026

A satisfying breakup song requires commitment. You need lyrics that leave no doubt who wronged you and ideally a music video starring someone who looks suspiciously like your ex. Justin Timberlake's "Cry Me a River" checked every box when it dropped in 2002 and helped launch his post-*NSYNC solo career. He spent nearly a decade refusing to confirm what everyone already knew. Which singer is "Cry Me a River" about?

Correct Answer: Britney Spears

(Source)

Not even full-body, matching denim outfits could save this relationship. Timberlake and Britney Spears broke up in early 2002, and after one particularly heated phone call with his ex, he stormed into Timbaland's studio and wrote "Cry Me a River" in about 90 minutes. The music video cranked the pettiness up even higher. The director said there was an unspoken rule to treat Spears' name like Voldemort on set, but that didn't stop Timberlake from handpicking a blonde look-alike specifically because she resembled Spears.

The track peaked at number three on the Billboard Hot 100 and won a Grammy, which is a solid return on 90 minutes of heartbreak. Years later, Spears revealed she had only kissed someone else after finding out Timberlake cheated on her first. Funny how that detail never made it into the Grammy acceptance speech.

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