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..
[That was] the first time I ever really felt the confidence to do it.
and debuted at number two on the Billboard 200 with first-week sales of 439,000 copies, fewer than previous 'N Sync releases. Later that year he recorded a song "I'm Lovin' It", used by Mc Donald's as the theme to its "I'm Lovin' It" campaign.
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.
Often cited as a pop icon, Timberlake is the recipient of numerous awards and accolades, including ten Grammy Awards, four Emmy Awards, three Brit Awards, and nine Billboard Music Awards.
From 2008 through 2012, Timberlake focused on his acting career, effectively putting his music career on hiatus; he held starring roles in the films The Social Network, Bad Teacher, Friends with Benefits, and In Time.
Timberlake resumed his music career in 2013 with his third and fourth albums The 20/20 Experience and The 20/20 Experience – 2 of 2, exploring neo soul styles, partly inspired by the expansive song structures of 1960s and 1970s rock.
His other ventures include record label Tennman Records, fashion label William Rast, and the restaurants Destino and Southern Hospitality.
He has two half-brothers, Jonathan (born September 12, 1993) and Stephen (born August 14, 1998), from Charles' second marriage to Lisa Perry.