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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.

Timberlake began to adopt a more mature image as an artist with the release of his debut solo album, the R&B-focused Justified (2002), which yielded the successful singles "Cry Me a River" and "Rock Your Body", and earned his first two Grammy Awards.

His critically acclaimed second album Future Sex/Love Sounds (2006), characterized by its diversity in music genres, debuted atop the U. Billboard 200 and produced the Hot 100 number-one singles "Sexy Back", "My Love", and "What Goes Around... Established as a solo artist worldwide, his first two albums both exceeded sales of 10 million copies, and continued producing records and collaborating with other artists.

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.

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".