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He played Jason Sharpe, a model who falls in love with a waitress after mistaking her for another model. The rise of his own stardom and the general decline in the popularity of boy bands led to the dissolution of NSYNC.Band member Lance Bass was openly critical of Timberlake's actions in his memoir Out of Sync.The idea of going solo was strengthened a year earlier. Could we do, like, 'N Sync featuring Michael Jackson', or 'Michael Jackson featuring 'N Sync'?Timberlake originally wrote the single "Gone" around 2001 for Michael Jackson, but he turned the song down, and was instead recorded by NSYNC. Timberlake declared in a later interview that the first time he felt confident to go solo happened after that conversation: [He] called me on the phone and said that he wanted to cut the record ("Gone"), but he wanted it to be a duet between himself and I. And he was very absolute about the fact that he wanted it to be a duet between himself and I..Upon the completion of the Celebrity Tour, the group went into hiatus in 2002.
His other ventures include record label Tennman Records, fashion label William Rast, and the restaurants Destino and Southern Hospitality.
In February 2004, during the halftime show of the Super Bowl XXXVIII broadcast on the CBS television network from Houston, Timberlake performed with Janet Jackson before a television audience of more than 140 million viewers.
At the end of the performance, as the song drew to a close, Timberlake tore off a part of Jackson's black leather costume in a "costume reveal" meant to accompany a portion of the song lyrics.
Timberlake, who cried during the episode, later admitted to being under the influence of cannabis when he was pranked.
Three episodes later, he set up Kelly Osbourne to be "punk'd", thus making him the first celebrity to appear on the show more than once.
Timberlake voiced the lead character in Dream Works Animation's Trolls (2016), which soundtrack includes his fifth Billboard Hot 100 chart-topping single, "Can't Stop the Feeling!