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Justin Timberlake is very popular, but has he ever done anything of substance?

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As the teenage pop rocket of the late '90s sputtered toward the new millennium, the record industry wanted to keep zooming. But who already among their proven ranks could age well and sell? Who could be counted upon?

They were covered with the women; the continued careers of Christina, Britney and Beyoncé mostly seemed to be sure things. But who from the boy band boomlet could last? Nick Lachey, JC Chasez and Nick Carter got boxier by the second, aging into figures better suited for reality TV shame than Tiger Beat frames. But there was Justin Timberlake, the multitalented lead cutie of 'N Sync and alumnus of the Mickey Mouse Club. He seemed to be the only viable choice. It was an early right-place, right-time break in a career consistently built less on quality than serendipity and canny positioning.

Unlike his still-boyish face, Justin's first solo work has aged poorly. 2002's Justified took the non-risky approach of emulating Michael Jackson's beloved early records. For a record supposedly patterned after Off the Wall, the dopey-ballad-to-actual-banger ratio is inexcusably high. It is particularly labored, too, the singer stuck in a talent-show falsetto that seldom seems to be anything more than carefully performed. He's a kid playing Casanova, ignorant of most under-the-sheets specifics.

More than a decade later, the one song that still leaps from the speakers is the Britney-done-me-wrong anthem, "Cry Me a River." The single was a creep move, anyway, a public chiding of a childhood friend and first love as their career trajectories traded shapes. Shame sells, though, and this song and its salacious nature cemented Timberlake's place as a solo star.

Though Timberlake's personal life might have been vital to the song's success, his voice was hardly irreplaceable. The things that make "Cry Me a River" so timelessly curious are quirks of Timbaland's production at a career peak—the pocket rain cloud that starts the track, the embedded shaman chants, the rhythmic stutter. It's full of stuff more interesting than its singer, a consistent thread throughout Timberlake's career.

That "Cry Me a River" ensured Timberlake's easy ascent from non-threatening boy band kid to lip-licking adult heartthrob speaks to the sexism ingrained into our pop culture machinery, the double standard of our collective expectations. All he had to do was age with a minimum of awkwardness, put on an expensive suit and defrost his tips. No one's ever branded sweet Justin a ruinous role model for young men everywhere. (Hello, Britney.) No weepy open letters were penned blasting Timberlake's role in his own exploitation. (Hi, Miley.) When he ripped Janet Jackson's top off during the Super Bowl halftime show, she was practically run out of the business. His role was barely mentioned.

To his credit, Timberlake never cracked publicly, but neither has Taylor Swift. Still, the likable and male JT never served as a shit magnet for the comparable string of famous singers, models and actresses he dated. It's his right as a famous young playboy, right?

By the time Timberlake built Justified's follow-up, 2006's Futuresex/Lovesounds, his voice had deepened a bit, and he'd toughened up. That album, his best to date, is hornier, works better in the club and depends upon self-consciously "adult" swagger. "Bitch" and "motherfucker" wormed their way into his (irrevocably) clunky rhymes. But even on his most hip-hop-centric album, he often gets upstaged by more talented guests—will.I.am, Three 6 Mafia, T.I., even Timbaland's halting anti-flow. The center seemed empty even as he occupied it.

Timberlake's reputation benefitted greatly from a critical softening toward pure pop in the early '00s. The buy-in to this record was near universal. Elite praise probably didn't add much to his bottom line. To wit, critically beloved Toronto group Junior Boys did similar work around the same time, with more skill and nuance, to a fraction of the sales. Still, the combined sales and the critical laurels of Futuresex/Lovesounds (more than 10 million copies worldwide, and No. 28 on the Village Voice's Pazz & Jop poll) sealed Timberlake's place as a universally liked artist.

Timberlake took a break from music after Futuresex, gaining acclaim as a multifaceted entertainer by leaning back toward an acting career. As with his music, his talent in this arena has been overstated. With typical fortuity, his one-note performance as Napster's founding douche Sean Parker in The Social Network gets far more attention than the garbage pile that is the bulk of his filmography. He's been a big part of spectacularly bad movies such as The Love Guru, Southland Tales, Trouble With the Curve and Yogi Bear. Friends With Benefits suggested that playing an affable romantic lead role was actually beyond his skill set.

His favorable reputation as a thespian can be cut into a handful of amusing Saturday Night Live stints and assorted publicity appearances on other late-night outlets."Mouseketeer reads cue cards with panache," offer the reduced headlines of the morning's celebrity sites. "Watch the video!"

Timberlake returned to music this year with the two-volume 20/20 Experience, billed as a benevolent attempt to give the people what they've demanded and not as a fallback option in the face of overestimated box-office potential. Apparently what the people want is the same underwhelming stuff, now cloaked in conspicuous luxury. The first, better volume is only another telegraphed claim for enhanced artistic maturity. The low end is muted and the run times bloated. String sections swathe everything, like high-thread count sheets that cover a lumpy hotel mattress.

Timberlake remains as lyrically awkward as ever, peppering his lover-man patois with formal-wear appreciation and tons of ill-sitting drug metaphors. It's not unpleasant music, exactly, but it trades the techno snap of Futuresex's singles for ponderous ambling. Every idea is stretched into emaciation. Dance with Mr. Timberlake! He finds you attractive! A second volume released later in the year reinforces that flaw to the point of self-parody.

But no one really seemed to notice: He's Justin Timberlake, after all, the universally loved charm-bot. It's a brand that's built to last.

This article appeared in print with the headline "Light power."

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