Timberlake co-starred in skit titled The Barry Gibb Talk Show alongside comedian Jimmy Fallon, where the duo portrayed Bee Gees brothers Barry and Robin Gibb.
It marked the beginning of a long-running friendship and collaboration with Fallon.
For his live performances, including the eponymous concert tour for the albums, he began performing with his band The Tennessee Kids, composed by instrumentalists and dancers.
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!
In its lifetime, NSYNC was internationally famous and performed at the Academy Awards, In late 1999, Timberlake appeared in the Disney Channel movie Model Behavior.
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.
The garment collapsed and her breast was accidentally revealed." Timberlake and Jackson were threatened with exclusion from the 2004 Grammy Awards unless they agreed to apologize on screen at the event.
Their second album No Strings Attached (2000) sold 2.4 million copies in the first week, and included a No. NSYNC's third album Celebrity (2001) was also financially successful.
Upon the completion of the Celebrity Tour, the group went into hiatus in 2002.
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.
The former became the best-selling album of the year in the US with the largest sales week, and spawned the top-three singles "Suit & Tie" and "Mirrors", while the latter produced the top-ten song "Not a Bad Thing".