4. Don’t restrict yourself to one genre
Actually, we’re getting ahead of ourselves. After Justified and that whole Super Bowl thing, Timberlake waited a few years to release a follow-up album, instead focusing his attention on acting. His first film, Edison, where he was surrounded by Morgan Freeman and Kevin Spacey, went unnoticed, while his second, the Sundance-screened Alpha Dog, got “meh” reviews, but Timberlake’s performance as a kidnapper was well received. And so it went, with Timberlake never settling on one genre of film; he’s done live-action comedies (The Love Guru), kids movies (Shrek the Third), whatever the hell Southland Tales was (Southland Tales), romantic comedies (Friends with Benefits), science fiction (In Time), and Sorkin (The Social Network). It showed he had range, as did his performance hosting SNL in 2003, and if the movie bombed, people could just say, “Hey, acting’s not his day job…”
5. Make a legitimately great album.
“…making music is,” and FutureSex/LoveSounds is a sexy pop masterpiece. On the 2006 album, Timberlake does the best Prince impression a white boy has ever done/will ever do, while also wisely going for an off-the-cuff, slick sound, which, unlike Justified, allows FutureSex to be remembered outside the context of when it was released. It sounds timeless and, most importantly, “cool,” the greatest compliment you can give to a top-40 artist.
6. Play against your image.
He’s also — please forgive the obviousness of this statement — really funny. Timberlake’s self-deprecating, possesses excellent comedic timing, has a knack for impressions, and is gung-ho for any sketch idea, like the time he put a cardboard box over his penis. He already had music fans in his pocket after FutureSex, but “Dick in a Box” — a brilliant spoof of Timberlake’s sexy image that made him perform the most awkward seduction act ever — won over comedy nerds, too, who couldn’t help but like him. It’s one of the rare things the 40-year-old slouched guy in the corner and the perky 16-year-old girl have in common, except for a shared attraction to 16 year olds. On top of all that, Timberlake hasn’t oversaturated the market with his image (consider him the Anti-Pitbull), he has an unassuming, boring personal life despite hobknobbing with the likes of Jay-Z, and overall, and perhaps most simply of all, he doesn’t seem like a douche, especially when he’s accompanying Marines to balls before it was cool.
7. The Hair
Forget everything I just said. JT’s successful because he ditched the ramen hair. The end.