The group would briefly reunite at the 2013 MTV Video Musixc Awards when Timberlake received the Michael Jackson Video Vanguard Award and at the 2019 Coachella Festival this time sans Timberlake who was finishing his 115-show Man of the Woods Tour.
Group member JC Chasez would later reveal during an interview with Lance Bass on March, 2020 that he discussed the possible performance with Timberlake over the phone and was given a positive response, stating Timberlake urged the group to perform without him and recounting that "Ariana (Grande) can sing my parts".
In August 2002, after months of recording "Justified", his debut solo album, Timberlake performed at the 2002 MTV Video Music Awards, where he premiered his first single, ""Like I Love You"," a sparse dance track produced by The Neptunes. The song reached number eleven on the "Billboard" Hot 100. Following the single, Timberlake released "Justified" on November 5, 2002. It debuted at number two on the "Billboard" 200 album chart, selling 439,000 copies in its first week of release. It eventually went on to sell more than three million copies in the U.S. and more than seven million copies worldwide. The album also received critical acclaim, thanks to its heavy R&B influence provided by hip-hop producers The Neptunes and Timbaland. It spun off hits throughout late 2002 and 2003, including the top ten singles ""Cry Me a River"" and ""Rock Your Body"." Timberlake supported the album by co-headlining the Justified/Stripped Tour with Christina Aguilera in the summer of 2003. At the end of the year, Timberlake recorded a song entitled "I'm Lovin' It." It was used by McDonald's as the theme to its "I'm Lovin' It" campaign. The deal with McDonald's earned Timberlake an estimated $6 million. A tour entitled Justified and Lovin' It Live was included with the deal as well. Timberlake was featured on Nelly's song, ""Work It"", which was remixed and included on Nelly's 2003 remix album.
In February 2004, during the halftime show of the Super Bowl XXXVIII broadcast on the CBS television network, 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. According to CBS, "both Jackson and Timberlake had confirmed they planned it 'independently and clandestinely' without informing anyone." Part of the costume detached, and Jackson's breast was briefly exposed. Timberlake later apologized for the incident, stating he was "sorry that anyone was offended by the wardrobe malfunction during the halftime performance of the Super Bowl..." The phrase "wardrobe malfunction" has since been used by the media to refer to the incident and has entered pop culture. As a result of the controversy, Timberlake and Jackson were threatened with exclusion from the 2004 Grammy Awards unless they agreed to apologize on screen at the event. Timberlake attended and issued a scripted apology when accepting the first of two Grammy Awards he received that night (Best Pop Vocal Album for "Justified" and Best Male Pop Vocal Performance for "Cry Me a River"). He had also been nominated for Album of the Year for "Justified", Record of the Year for ""Cry Me a River"", and Best Rap/Sung Collaboration for "Where Is the Love?" with The Black Eyed Peas.
After the Super Bowl controversy, Timberlake put his recording career on hold to act in several movies, having starred in a few feature movies earlier in his music career. The first role he took during this time was as a journalist in the thriller "Edison Force", which was filmed in 2004 and received a direct-to-video release on July 18, 2006. He also appeared in the movies "Alpha Dog", "Black Snake Moan", Richard Kelly's "Southland Tales", and voiced Prince Artie Pendragon in the animated movie "Shrek the Third", released on May 18, 2007. He also appeared as a young Elton John, in the video for John's song "This Train Don't Stop There Anymore". Timberlake was considered to play the role of Roger Davis in the movie version of the rock musical "Rent", but director Chris Columbus had insisted that only the original Broadway members could convey the true meaning of "Rent".
He continued to record with other artists. After "Where Is the Love?", he again collaborated with the Black Eyed Peas on the 2005 track "My Style" from their album "Monkey Business". When recording the 2005 single "Signs" with Snoop Dogg, Timberlake discovered a throat condition. Nodules were subsequently removed from his throat in an operation that took place on May 5, 2005. He was advised not to sing or speak loudly for at least a few months. In the summer of 2005, Timberlake started his own record company, JayTee records.
Timberlake made a cameo in the video for Nelly Furtado and Timbaland's single "Promiscuous", released on May 3, 2006.
Timberlake released his second solo album, "FutureSex/LoveSounds", on September 12, 2006. The album, which Timberlake created in 2005, debuted at number one on the "Billboard" 200 album chart, selling 684,000 copies its first week. It is the biggest album for pre-orders on iTunes, and beat Coldplay's record for the biggest one-week sales of a digital album. The album was produced by Timbaland and Danja (who produced a bulk of the album), will.i.am, Rick Rubin and Timberlake himself, and features guest vocals by Snoop Dogg, Three 6 Mafia, T.I. and will.i.am. A studio representative described it as being "all about sexiness" and aiming for "an adult feel".
The album's lead single, "SexyBack", was performed by Timberlake at the opening of the 2006 MTV Video Music Awards and reached number one on the "Billboard" Hot 100, where it remained for seven consecutive weeks. "My Love", the album's second single, also produced by Timbaland and featuring rapper T.I., reached number one on the Hot 100, as did third single What Goes Around.../...Comes Around Interlude. The song is reported to have been inspired by the break-up of his childhood friend and business partner, Trace Ayala, with actress Elisha Cuthbert. In October 2006, Timberlake said that he would focus on his music career rather than his movie roles, specifying that leaving the music industry would be a "dumb thing to do at this point". He was the special guest performer at the 2006 Victoria's Secret Fashion Show for being where he sang SexyBack.
In January 2007, Timberlake embarked on the FutureSex/LoveShow tour. "Summer Love/Set the Mood Prelude" was the fourth U.S. single off the album, and the next single in the UK was "LoveStoned/I Think She Knows Interlude". The song "Give It to Me", a Timbaland single on which Timberlake guests with Nelly Furtado, reached the Hot 100 number-one spot.
In February 2008, Timberlake was awarded two Grammy Awards. At the 50th Grammy Awards Ceremony, Timberlake won the "Male Pop Performance" Award for "What Goes Around...Comes Around", and the "Dance Recording" Award for "LoveStoned/I Think She Knows".