“Justin Timberlake entered the industry as a kid on Disney’s New Mickey Mouse Club, he went on to front the hugely popular boy band ‘N Sync and gained lots of media attention for his supposedly chaste romance with Mickey Mouse castmate Britney Spears.
For Justin, launching a successful solo career meant exiting the boy-band space occupied by white crooners like the Backstreet Boys and 98 Degrees and entering one dominated by black R&B and hip-hop artists.
With production by Timbaland, The Neptunes and P. Diddy, Timberlake’s solo debut, “Justified,” thrived on his novelty: He was the white boy with the bleached blonde fade and vague hip-hop swagger who could really sing the black music he unabashedly recorded. Image-wise, he picked, chose and performed suave and often provocative black masculinities embodied by the likes of James Brown, Michael Jackson, and Prince. For that he was richly rewarded; the album sold more than 7 million copies worldwide and he won two Grammys, ironically for Best Pop Vocal Album and Best Male Pop Vocal Performance.
But when shit hit the fan after the 2004 Super Bowl when he exposed Janet Jackson’s nipple on live television, he was able — after making a public apology on CBS — to easily revert back in the public’s imagination to the wholesome white boy who made pop songs for teenage girls. And that’s what becomes tricky with Justin, that his whiteness acts as both an entryway into a popular culture and a buffer against its criticisms. Janet’s career, on the other hand, stagnated. (Black comedy legend Paul Mooney famously dubbed the scandal her “n*a wakeup call.” And Chris Rock blamed her exposed “40-year-old breast” for creeping censorship in American television.)
Justin wouldn’t likely have that musical freedom without his work in very white Hollywood. Despite early, notable flops (“Black Snake Moan,” “Alpha Dog”) he’s been able to build a movie career, generating Oscar buzz by playing Sean Parker in the “The Social Network,” doing raunchy, satirical comedy opposite Cameron Diaz (“Bad Teacher”), and straight-ahead romantic comedy opposite Mila Kunis (“Friends With Benefits”). Without Hollywood, his wedding to Jessica Biel might not have landed them both the cover of People magazine. He’s also hosted “Saturday Night Live” five times, a testament to his comedic chops and a larger-scale Hollywood visibility that he wouldn’t likely have access to without his whiteness.”"
— Jamilah King, “The Trouble With Justin Timberlake’s Apprporiation Of Black Music,” Colorlines 3/22/13