Justin Timberlake Covers T The New York Times Style Magazine!

He sings, he dances, he acts, and he’s not afraid to get silly in self-mocking comedy shorts. Drawing a line from Frank Sinatra to Jay Z, Justin Timberlake has become this generation’s master of ceremonies.

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JUSTIN TIMBERLAKE IS PLAYING the long game. He’s the Kasparov of showbiz. He has survived far longer than most artists, tracing an arc from pop-culture absurd — first appearing on the Mickey Mouse Club at age 11 — to pop-culture sublime, a solo career that has triumphed at a time when entertainment, and celebrity, have become more disposable than ever. “I’m 32,” he says over coffee this summer in downtown Manhattan. “I know that I’m still young, but I’ve been in this business two-thirds of my life and you just learn that some things are accepted the way you hope and some aren’t.”

Justin Timberlake, now 32, has spent years building on his eminent charm in music, film, and even comedy to revive the idea of the all-around entertainer for a new generation. More…

To a remarkable degree, across multiple disciplines, they have been: his band ’N Sync’s success, at its time, rivaled that of the Beatles; teeny-bopper adulation could’ve been a velvet coffin, as it was for other members of his group and that of the other ’90s phenomenon, the Backstreet Boys. But Timberlake methodically worked his way out of it, rebranding himself as a dapper solo artist, a picker of modest but choice acting roles (most notably as Sean Parker in “The Social Network“) and as a master of this generation’s gift to comedy, the viral short. The digital shorts he created with the music-comedy trio the Lonely Island, and his “Saturday Night Live” skits, centered largely on parodies of oversexed ’90s R&B stars. They also served to gently distance him from his teenage self, less oversexed than, say, the members of Jodeci, but perhaps similarly mockable. He also, smartly, knew when to shut up, going AWOL from music for almost seven years, absent some key collaborations, before returning this spring with a complex, densely produced best-selling album, “The 20/20 Experience.”

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“You get to this point, which I’ve done in the last five or six years, where you become less worried about success and failure,” he says, speaking of “20/20,” which is filled with eight-minute rave-ups and signature Timbaland trance-outs. He may be only in his early 30s, but he has taken on the philosophical aspect of someone a generation older. “I’m sure there’s some self-help cheese-ball book about the gray area,” he says, “but I’ve been having this conversation with my friends who are all about the same age and I’m saying, ‘Y’know, life doesn’t happen in black and white.’ The gray area is where you become an adult . . . the medium temperature, the gray area, the place between black and white. That’s the place where life happens.”

Others spend years in obscurity, carving off pounds of credibility for meager dollops of fame. Timberlake was more or less born famous, disposably so, and then fought his way to something more real and lasting. And he has done it over a two-decade span that has been marked by rapid-fire cultural churn, building up and tearing down artists at a manic pace. You jump on the party bus only to see it crash in a ditch moments later. Timberlake’s secret has been to remain detached from these hyper-accelerated comings and goings of fad, trend, in, out. “If you can answer the question of why you’re doing it, it’s the right thing to do,” he says in Mr. Miyagi mode, describing his decision to put out his first album since “FutureSex/LoveSounds” in 2006, a gap in content production that would have spelled doom to a lesser talent. “To answer the question ‘Why?’ for the first time in my career, is: because I wanted to.”

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This year, among other things he wants to do, is put out the second part of “The 20/20 Experience,” which he describes intriguingly as the “hotter, older evil twin sister” of “20/20,” and then, even more intriguingly: “If you could imagine you’re 16 and she’s everything you thought. She’s Marilyn Monroe and then you meet her older sister; everything that’s dark and wrong about her at that age is why you become infatuated with her.” Hot, older “20/20″ will be supported by a major arena tour this fall.

This, after he headlined a sold-out stadium tour this summer with Jay Z, an intermittently awkward and thrilling pairing of two very different showbiz traditions, or at least two people who learned very different things watching Frank Sinatra. Jay Z took Sinatra’s suit-and-tie phlegmatic self-confidence, merged it with hip-hop’s swagger and created a model for the 40-plus black artist/businessman that is unprecedented in the genre. Timberlake took from the crowd-pleasing Sinatra, bringing back the idea of the “performer”: the all-singing, all-dancing entertainer, whose craft didn’t interfere with showing the fans a good time. Along the way, thanks in part to the growing amount of time spent collaborating with Jay Z, he has modeled a new kind of postracial, postmacho white male.

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