Timberlake pulled off a successful crossover from ‘NSync boy band idol to solo artist with his album Justified. Even more impressively, his music has not only sold well, it’s critically acclaimed.
In 1995, Timberlake formed ‘NSync with friends, including MMC costar Chasez. The band’s 2000 album No Strings Attached was the fastest-selling album of all time.
In 2002, Timberlake’s solo album Justified began his transformation from a clean-shaven boy to an edgy, dangerous man, and improbably, the transition worked. His second solo album FutureSex/LoveSounds, which debuted in 2006, cemented his reputation as a top-selling sensation.
In 2004, the record producer accidentally exposed Janet Jackson during their performance at the Super Bowl halftime show, which became a major scandal. Timberlake later noted that he had privately reached out to Jackson about the incident.
Timberlake’s first public courtship was a four-year relationship with Britney Spears, however, after rumors surfaced that Spears was unfaithful, the couple split. The Tennessee native received backlash for the way he handled the aftermath of the breakup when the Framing Britney Spears documentary was released in 2021. At the time, Timberlake released a public apology to Spears and mentioned Jackson again as he addressed inequality in the entertainment industry.
In early 2006, Timberlake officially parted ways with longtime love Cameron Diaz, whom he started dating after they met at the Nickelodeon Kids’ Choice Awards three years prior.
The songwriter started dating Jessica Biel in 2007 and they briefly called it quits two years later. After getting back together, the duo got engaged in 2011 and had a wedding ceremony in Italy the following year. They welcomed son Silas in April 2015 and son Phineas in July 2020.