Justin Timberlake, From Boy Band King to Bad Boy Headlines: Full Timeline

From boy band heartthrob to headline-making solo star, Justin Timberlake’s journey has been anything but quiet.
It all kicked off with *NSYNC in ’95 … hitting red carpets with Britney by 2000, and the group performing a now-iconic Super Bowl halftime show with her and Aerosmith in 2001.
After the band hit pause in 2002, so did his relationship with Brit — cue “Cry Me a River” drama. But he moved on quickly … dating Cameron Diaz, performing solo at the MTV Music Video Awards, followed by his own album release — before getting caught red-handed in the Janet Jackson Super Bowl scandal in 2004. He went on to date and later marry Jessica Biel, and made the jump into movies like “The Social Network.”
And since then, JT’s still making noise — think apologies, cheating rumors, a shocking abortion reveal from Britney … and a DWI arrest in 2024. Watch our full timeline for the breakdown.
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