Even if some critics panned him for mimicking the King of Pop (the Los Angeles Times called the number "a wan evocation"), Timberlake is "embarking on something critical," he told PEOPLE in May. Stepping away from 'N Sync—and his ex-girlfriend Britney Spears—he'll release his first solo CD, Justified, on Nov. 5. The response so far has been overwhelmingly positive: The disc's "well-drawn R&B-leaning songs" said Billboard, "are notable for their decidedly earthy, often retro tone—a sharp, mature shift from 'N Sync's more glossy teen-pop output."
Of the five in the boy band, which has sold more than 27 million records since it formed in 1995, Timberlake is "the whole package," says 'N Sync creator Lou Pearlman, who has since parted ways with the group. "He can go all the way." But will he leave his bandmates behind? No, Timberlake told TEEN PEOPLE; for now, he just wants to "do my own thing" with music that, says Justified engineer Andrew Coleman, has "more of a rock vibe."
His maturing sound has plenty of emotional roots. Eight months after the four-year romance with Spears, 20, ended, fans are still wondering why. "Everyone was interested," says Bobbye, "even people my age. I think it's just because they were like the little bride and groom on top of the wedding cake, a little Ken and Barbie." Rumors flew, but the pair—who first met on The Mickey Mouse Club in 1993—have stayed mum. "I love Britney," Timberlake told the U.K.'s Heat magazine last month. "I just think our timing was off." Yet his new song "Cry Me a River" seems to imply that Spears cheated on him, a charge that she has denied: "You don't have to say what you did/I already know..."
Since the split, he has found solace in his new $8 million Spanish-style Hollywood Hills home and a string of reported flings, including with 'N Sync backup dancer Jenna Dewan, 21, and Janet Jackson, 36. ("They have seen each other," says Bobbye. "Justin has had a crush on Janet since he was very small") Since August Timberlake has been dating Charmed star Alyssa Milano, 29, whom he takes to L.A. clubs and visits on the set of her show. "They are not all over each other," says Allan Davis, co-owner of A.D. and the Lounge, where the duo hang out at least once a week. "They make a nice couple." Adds a close friend: "Right now they are not boyfriend and girlfriend. They are just having a good time."
That goes for his posse too. Not a boy, not yet a man, Timberlake loves to duel pal and mentor R&B singer Brian McKnight, 32, on Xbox and PlayStation—when they're not tooling around in their sports cars (Timberlake drives a Dodge Viper and Cadillac Escalade). "We're just like little boys," says McKnight.
But Timberlake, a Memphis native, also speaks to his mom and comanager, Lynn Harless, 41, every day and flies home to Millington, Tenn., every few months to see her and his dad, building contractor Randy, 43, who split with Harless when Justin was 5 and is now remarried with two sons. And yes, Justin and his mom have talked about Britney. Says his mom: "When he calls and says his heart is broken, we try to console him."
Beverly Keel in Nashville, Pamela Warrick and Frank Swertlow in Los Angeles, Steve Helling in Orlando and Theresa Crapanzano and Ansley Cichy in Virginia Beach, Va.