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Billboard’s Greatest Pop Stars of the 21st Century: No. 14 — Justin Timberlake

Justin Timberlake is our No. 14 Greatest Pop Star of the 21st Century for how he set the standard for pop excellence for most of the 2000s.

What should have been a victory lap for the newly minted solo star turned into a world-famous nightmare when Timberlake accidentally exposed Jackson’s breast in front of 140 million TV viewers (just as he sang the “Rock Your Body” lyric “better have you naked by the end of this song”), later coining the infamous phrase “wardrobe malfunction” in his apology. His comments were prompted by the February 2021 release of the documentary Framing Britney Spears, which put his post-breakup behavior in a new light and led to renewed criticism over the double-standard at play following the Super Bowl controversy, and Timberlake’s failure to properly support Jackson over the blowback she’d faced at the time, which he’d since expressed regret over. After all, while he’s surely picked up fans along the way who weren’t around for his *NSYNC heyday – whether they were too old to be invested in a boy band or too young to understand (or not even alive for it, for that matter) – the bond formed from watching someone at age 12 on Disney Channel to following along on their boy-band journey to seeing their ascension to the top of the pop pyramid is impossible to replicate.

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