Justin Timberlake is preparing to serenade me.

    Sitting in the kitchen of producer Timbaland's Manhattan recording studio 24 hours after his amped-up appearance on the MTV Video Music Awards, the 21-year-old pop star tunes an acoustic guitar between sips of tea. Clad in a white track suit, he seems relaxed and focused on the task at hand. "I'm not no Hendrix or Santana [sic]," he says with a bashful smile. "I took [guitar] lessons for about three weeks and got so bored with it I just figured I'd teach myself."

    He strums a few tentative chords, then launches into the 'N Sync hit "Gone," which he wrote for Celebrity, the group's 2001 album. "There's a thousand words that I could say/To make you come home," he sings in a honey-dipped falsetto. "Seems so long ago you walked away/Left me alone..."

    Thoughts flood the mind: How many kazillion teenage girls would barter their weekly allowances in perpetuity to be here right now? Just how much would a bootleg recording of this intimate moment be worth? Most important: Is this really a song one straight guy should be singing to another?

    Actually, Timberlake's mini-concert isn't intended as any kind of touchy-feely sensitive-male bonding ritual--he's just demonstrating that, contrary to the opinions of naysaying critics, he's a real musician, one for whom the creative process comes naturally. "A lot of people want to act like songwriting is brain surgery," he says. "It's not. It's as easy as"--he plonks a chord cluster--"that."

    Well, maybe. It remains to be seen if Timberlake's present endeavor--launching a successful solo career outside the heretofore comfy confines of the 'N Sync mother ship--will prove so simple.

    Timberlake's debut solo album, Jusified, is due Nov. 5. It's not your little sister's pop music. To give it street cred and that state-of-the-art, club-friendly sheen, he's enlisted the aid of some of hip-hop's hottest producers--Pharrell Williams and Chad Hugo of the Neptunes, Timbaland, Andre Harris and Vidal Davis, P. Diddy. The hope is that dazzling big production numbers like "Senorita" and "Cry Me a River" will decisively distance Timberlake from the sort of treacly teen pop that catapulted 'N Sync to stardom. "The bubblegum sound is old," says Timberlake, whose personal tastes run to current rap and classic soul. "That's obvious. You can't do 'Bye Bye Bye' twice."

    'N Sync manager Johnny Wright (who comanages Timberlake with the singer's mother and stepfather, Lynn and Paul Harless) agrees, going so far as to admit that "the traditional five-member, male pop vocal group is starting to fizzle." Wright thinks that Timberlake can both retain his core teen audience and attract new fans with Justified.

    "As your musical tastes open up, at some point what you personally like and want to do might not be in the best interests of the group," says Wright. "So, when you have that passion, you have to step out and present it, and that's what Justin did. All he wanted to do was go out and put some music on CD that was in his heart and get a reaction from fans one way or the other. This is all about the passion and the music inside of him."

    Timbaland, who produced and cowrote four songs for Justified, gives his young charge credit for trying to branch out sonically. "At first, I was like, He's coming from 'N Sync, I'm coming from my urban world--how we gonna mesh?" he says. "But when we got together, everything was perfect. We worked real good together. It's hard coming from 10 million sales to switch up styles on your fans and do something different, but he's just being him. I'm down with taking chances 'cause I'm a chance-taker myself."

    Williams said he bonded with Timberlake from their first meeting at the New York City nightclub Spa, and welcomed the opportunity to work with him. "This is not Justin from 'N Sync's solo album," he says. "There's a difference. The guy is talented. He's a dope individual. He knows what he likes and he knows what he wants, and he was very easy to work with. I think it's his moment."

    Indeed, it seems logical for the ambitious young pop idol to bust a new career move. In reality, it may be as much a matter of necessity as choice. Let's face it: All those 12-year-old chickadees who scarfed up 'N Sync's self-titled 1998 debut and its two megaplatinum follow-ups, No Strings Attached (2000) and Celebrity (2001), are that much older now. Many have graduated to more challenging musical fare: Eminem, the White Stripes, Jay-Z, the Hives. And with his bandmates all chasing various rainbows--Lance Bass trying (and thus far failing) to blast off into space, Joey Fatone starring in the Broadway musical Rent, Chris Kirkpatrick seeking to become a fashion maven, and JC Chasez dabbling in electronica--a fourth 'N Sync album doesn't seem to be topping anyone's list of priorities (although Wright says he anticipates there will be a new CD in the fourth quarter of 2003).

    Timberlake had his official coming out party as a solo artist at MTV's VMAs. He performed his new single, "Like I Love You," which he cowrote with the Neptunes. While he judges his performance a success--"I didn't fall down and bust my ass on stage. That was good"--the spectacle seemed to generate more bemusement than excitement. The song itself, Timberlake's pop-locking dance moves, even that black hat slung low over his brow were all eerily evocative of Michael Jackson--so much so that some came away thinking the entire production was a de facto Jacko homage. (Rendering the proceedings even more surreal was birthday boy Jackson's brief onstage appearance at the VMAs in the company of ex-Timberlake squeeze Britney Spears.)

    "It's obvious he was really just copying Michael, and I don't think that's necessarily the best way to go," says thirtysomething fan Stephen Roderick. "He really needs to find his own style, something more original."

    Wright begs to differ: "In reality, there was no thought about [copying] Michael Jackson. [The idea for] the hat actually came from Frank Sinatra, but nobody even thought about Justin vibing on Frank Sinatra. You can't grow up in the era of Michael Jackson...without having some of that imbedded in your soul. But there wasn't a thought in his mind to go out there and try to be Michael Jackson."

    Timberlake readily admits to the Jackson influence but thinks he brought something more to the table than recycled Thriller moves: "Anytime someone comes out and dances and does something with choreography, they say, 'Well, that's inspired by Michael.' The responses I've been hearing are that [my performance] was reminiscent of Michael, but at the same time, I did my thing."

    As it happens, Timberlake's solo strike coincides with that of a rival, Backstreet Boy Nick Carter, who just released his first single, "Help Me," and whose own pop-rock-flavored album is due Oct. 29.

    "It's almost like Survivor on TV, but in the musical business," says Paul "Cubby" Bryant, music director of New York radio station Z100. "The boy-band phenomenon is over, now who's gonna break out and be successful? It's like a cycle that happens every 10 years when the boy bands break up and you wonder who's gonna emerge victorious."

    What Bryant doesn't mention is that there's virtually no precedent for prefab teen idols sustaining significant careers once the kiddies lose interest. From Peter Tork, Bobby Sherman, and David Cassidy to Marky Mark and the Funky Bunch and the Spice Girls, yesterday's Tiger Beat pinups almost invariably end up as footnotes.

    Yet Timberlake--long considered the most charismatic 'N Syncer--is ready to buck the odds. "I don't know what some 15-year-old is gonna think about [my album]," he admits. "I don't know what a 30-year-old is gonna think about it. But I'll know soon. I really didn't change my formula too much. It's not like I was trying to be Rob Zombie or someone I'm not. I didn't talk about anything that I don't know about--like thuggin' in Harlem."

    "I met Eminem for the first time ever last night [at the VMAs]," says Timberlake, pride and excitement commingled in his voice. "We passed each other in the hall at Radio City and I said, 'Congratulations on your awards, I really think you deserve [them].' He said, 'Thanks, man, I appreciate it,' and gave me a five and kept walking. To me, it was like a mutual respect. I'm such a big fan of his."

    While it's as likely as not that the pair's encounter may afford Eminem fodder for a derisive lyric down the line, Timberlake's delight at genuflecting before this particular hero is telling. He may be the youngest member of 'N Sync, but at 21 he's certifiably a man, eager to put away childish things. Earlier this year, he ended his relationship with Britney Spears, whom he had first met back in 1993 when the two starred in the variety series The Mickey Mouse Club. Recent reports have linked the ex-Mouseketeer with Janet Jackson, 36, with whom he recorded a song "Take Me Now," for Justified. Aside from adding an interesting dimension to his apparent Jackson family obsession, the Janet/Justin rumors are particularly tabloid-friendly given the age difference between them.

    But if Timberlake has converted to the older-women-make-better-lovers school of thinking, he won't cop to it.

    "I love Janet to death," he says. "I know her very well. She's a sweetheart. 'N Sync opened for her when she did the Velvet Rope Tour. I've been linked [romantically] to so many different people, and it's retarded. I know Janet, she knows me. We're friends, and there's nothing in the world that would change our friendship. The same thing with me and Britney. We're still friends. If we part ways on our terms, that was on our terms, and it's nobody else's business."

    Timberlake describes himself as single, and says he's "definitely enjoying" his freedom: "I feel like I can look and really figure out [what I want]. I'm definitely a one-woman type of dude. But I have this whole theory on dating. You know how you go on a job interview and you meet the secretary and she's beautiful and she's sweet and she looks like she's having such a good time doing what she's doing? And then you finally get in to meet the boss, and he's an ass.... I feel like [with dating], you go through four to six weeks of the secretary, and then you meet the boss."

    Hmmm. Sounds like somebody has grown up. And with a legion of metaphorical secretaries and bosses--not to mention critics, gossip columnists, and curious onlookers--clocking his every move, only time will tell just how well Timberlake's working sabbatical pays off.

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