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Why Is Justin Timberlake The Only Youngster Who Can Stand Up To Sting?

If Sting wins a Grammy for Best Pop Male Vocal Performance this year, it will be the fourth time he will have had the honor bestowed upon him since 1992. Eric Clapton didn’t release a studio album in 2003, but if he had, you could wager with confidence that he’d be up for the award too, having won three times since 1992.

As usual, most of the Pop Male Vocal playing field this go-round is dominated by old-timers: Sting, Michael McDonald, Warren Zevon, who died of lung cancer last September, and George Harrison, who died of cancer in 2001.

One artist in the pack, however, conspicuously defies the dinosaur stereotype: Justin Timberlake, for “Cry Me a River.” Granted, each year one or two under-30 crooners get an obligatory nod. Craig David and Brian McKnight were nominated in 2002, Ricky Martin and Marc Anthony in 2001, and Eagle Eye Cherry and Shawn Mullins in 1999. But this year Timberlake’s got a good shot at claiming the prize.

“Cry Me a River” isn’t just a youthful pop song or a traditional love ballad. It’s a confessional lament that resonates with sincerity and soul. “Like I Love You” may have bought Justin credibility in the hip-hop community, but it was “Cry Me a River” that marked his transformation from doe-eyed teenypopper to pained and relevant singer/songsmith.

The number was written about the dissolution of Timberlake’s romance with Britney Spears, and the personal subject matter lent the song poignancy. “It was easy for us to capture a vibe in the studio because there was meaning behind it,” said Scott Storch, who worked on the track with Timberlake and producer Timbaland.

Grammy voters aren’t quick to praise even the most heartrending efforts of young ‘uns. Teen pop stars’ sentiments are often considered shallow or insincere. To rise above that bias, a singer has to deliver a top-notch performance that’s both emotionally genuine and musically exceptional, which Timberlake pulled off.

“Justin sounds great on that song,” Storch said. “He has a passion for classic soul music, and he’s learned lots of tricks from back in the day that he’s applying to modern music. He’s sort of a return to blue-eyed soul. I’d compare him to Daryl Hall in terms of so much soul coming from a white guy.”

Timberlake clearly has a voice to match his charm and dancing ability, but it’s unclear why more young white guys lack similar skills. Perhaps being a convincing singer requires life experience. While Clapton and Sting have lived through divorce, addiction and depression, and channeled their feelings into emotion-laden songs, the same can’t be said of Nick Carter, Nick Lachey or O-Town. Maybe losing the girl he thought he’d spend the rest of his life with made Timberlake’s voice so vulnerable and affecting.

“I was feeling angst in the form of heartbreak, and it was eating me alive,” Timberlake said shortly after the record’s release.”[Recording] it was like a whole big spa treatment. I just got better and better, and at the end of the record I was like this person who had just let it all go and said, ‘Wow, I’m over it. I’m past this. I’m in a good place.’ ”

To build a patio, though, you’ve got to have the right tools. Timberlake has listened to classic R&B from an early age and can reference the vocal inflections and tonal structures necessary to make “Cry Me a River” a real tearjerker.

“Part of the soul Justin has comes from his upbringing and personal taste in music,” Storch said. “He definitely started on the right path when he was young, and that’s why he can touch on some real singing and really soulful things. It’s rare to hear that ability in guys. You’ve heard it more from females like Christina Aguilera, but he definitely has incredible ability.”

“People recognize that it’s not contrived at all,” Timberlake added. “I grew up on Stevie Wonder and Marvin Gaye and Al Green, and that stuff’s still with me.”

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