Justin Timberlake, The Bachelor

Rolling Stone's 2003 cover story: before he was engaged to Jessica Biel, he was pop's Mr. Heartbreak

justin timberlake rs914
Herb Ritts
Justin Timberlake on the cover of Rolling Stone.
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A month to the day after the release of his solo album, Justified, which has sold more than 1 million copies, and ten days after the debut of his controversial ex-girl-friend-slamming "Cry Me a River" video, Justin Timberlake rolls himself out of bed inside the house where he grew up, near Memphis; hobbles downstairs in his shorts, yawning and bleary-eyed; greets his mom, Lynn Harless, who has been busy cleaning; greets the family dogs, Bearlie and Bella, who have been busy yapping; looks outside at the woods in his backyard and says, "Did I hear somebody say something about food?"

He's been home for three weeks, recuperating from a broken foot that forced him to cancel all Justified promo activities. Last night he went to an Aerosmith concert in town. A few days before that, he went out on a date with a local girl, an astounding thing for him. But, for the most part, he's just been vegging on the couch in the living room, playing video games (Halo, usually), expanding his stomach and letting his mom take a mom's good care of him.

"Here's what I want," he says at last.

"A Philly cheese-steak sandwich," she says, already knowing.

"Yeah. And a salad. And regular fries."

Timberlake bends down to mess with the dogs.

"The doggies are so glad to have him home," Harless says fondly. "They miss him. Actually, this is the longest time he's been home since he left, when he was fifteen."

Easing himself around the couch, Timberlake takes a seat and says that he's feeling pretty good and relaxed, with his album now out and its first two singles, "Like I Love You" and "Cry Me a River," mixing it up on the charts. Recorded with hip-hop and R&B kingmakers the Neptunes and Timbaland, Justified is a collection of loose and swinging dance-floor funk. At Timberlake's insistence, much of it was cut live in the studio, and its confident sound – a combination of Seventies atmosphere and '02 know-how, and about as far away from 'NSync's kiddie pop as you can get – confirms his sharp musical instincts.

"You know what?" he says. "I turned on TRL the other day, and I'm the old guy now. Avril Lavigne and B2K, they're the new little faces of teen pop, as much as they'd tell you to fuck off if you told them that. As for me, I'm somewhere in the middle, starting from zero, rebuilding my whole base. This year has been all about change. Big change. I ended a four-year relationship. I bought a house in L.A. I embarked on a solo career. And, on top of that, I did it all in front of the world, without losing my head. And now, for the past three weeks, I've been here, away from the world. It's been really good."

Of course, it hasn't been all good. His performance at the MTV Video Music Awards received a lot of flak, because he hit the stage dressed like Michael Jackson – gloves, cocked hat – and danced a lot like him, too. More recently, on a New York radio station, he came out and said he'd gone down on Britney Spears during their time together, a crass admission that led to much negative attention. Then there were all the tabloid reports surrounding his alleged romantic exploits with Janet Jackson, Christina Aguilera and Alyssa Milano. And now there's that new flap over the "Cry Me a River" video.

Just for a second, Timberlake thinks about sliding the video into the VCR. It's a peculiarly unsettling four minutes and forty-eight seconds of psychodrama, about a guy who gets even with his cheating girlfriend – a Britney-look-alike girlfriend – by making it with another woman, taping it and leaving the tape for the girlfriend to see. The video is full of Britney imagery – it's got her trademark newsboy cap, Porsche Boxster and sunglasses, and a fairy figurine similar to the one tattooed on her back. But then Timberlake decides that maybe now is not the right time to play the thing. Instead, he starts talking about Spears and about how, early on, he felt blamed for the breakup, when it wasn't his fault at all, and before long he's moodily saying, "I think I still have a lot of feelings, though I don't particularly know what they are."

The Timberlake home is located in an estate-type subdivision twenty miles outside Memphis. It's brick, of a goodly but not ostentatious size, and has a Tudor feel to it, with a neatly manicured front greensward. Inside, Harless has done the place up with statues on tables, comfy couches and a few framed photographs of her son, which he turns face down when she isn't looking and she turns face up when he isn't looking. Upstairs on a balcony is Timberlake's full-size Revenge From Mars pinball machine. Hogging space next to the landing is his gigantic suitcase, which he has yet to unpack. In the living room, two TV sets face each other, with two back-to-back easy chairs situated between them; this is where Timberlake and his lifelong best friend, Trace Ayala, play Halo on the Xbox they bought at the local Best Buy.

Timberlake's parents divorced when he was two; two years later, his mom, now forty-one, got remarried, to Paul Harless, a local banker, and together they raised what to them seemed like a very quiet child. "He always walked around with his head down, so you never saw anything but the top of his head," says Lynn, a trim, attractive woman. She remembers her son as a "perfectionist [who] couldn't stand anything on his shoes or his hands." The two were, and are, exceptionally close. She came up with the name 'NSync, and ever since his Mickey Mouse Club days, when it all got started, she's been his co-manager. Lovingly enough, Timberlake has a tattoo on his back of an angel holding a banner that bears his mom's initials.

One great thing about Timberlake is that, while he's no longer all that quiet, he's still as friendly and open as he must have been as a kid. Sure, much has changed since 'NSync began cranking out their four albums; but much is the same, too. Timberlake has given no thought to deep-sixing 'NSync; in fact, he and the guys are slated to start a new album in the fall. Plus, it's not like his family has uprooted itself, moved to Los Angeles, bought Bentleys, gone in for plastic surgery and fallen out with one another, lawsuits resulting. They've all stayed put, which is why Timberlake has a home to go to. He's comfortable here, resting up until he has to embark on a promo tour that will last until February, which will be followed by a club-date tour in the spring and an arena tour in the summer. So anything you want to talk to him about, you go right ahead. Pretty much, he's game.

He says that when he listens to Eminem, it makes him want to "beat the shit out of somebody – and if you can give me a feeling like that with a song, man, that's music," though he thinks Eminem probably wouldn't like Justified at all. He says that during his acne years, he was popularly known as Pizza Face and that, as a kid, he attended a nearby Baptist church with his folks but felt rejected by its frowning, judging elders and eventually found his own place with the Lord, no church required. "I can honestly say I am a Christian, but my spirituality has been developed on the road and is based on my experiences with God." He claims to never have been a frequent masturbator. "Definitely not frequent. Actually, I'm not a huge fan of it. I mean, it is what it is, a safe haven, there when you need it, and I don't feel guilty about it. But I always like to do everything at its best, and that just seems like settling, doesn't it?"

He says, often and without prompting, that he loves his mother very much. The two spend lots of time together away from home, too. (In fact, the tabloids reported seeing Timberlake and his mom before Christmas at the club Lotus in New York, sharing a joint.) "We have a very special relationship," he says. "She's been my best friend since I figured out who I wanted to be. She's great, and such a fun woman. She goes out with me and stays out later than I do. She's always been there beside me, and I think that's part of my problem with girls. You keep searching for somebody as good as your mother, and that's a losing battle."

It's been quite some journey for him, of course, an improbable slue to fame that seems to have left him kissed by blessings in all areas of life except one. And that one follows him around like a bad dream.

A few months ago – after attending the Mike Tyson-Lennox Lewis dust-up in Memphis and buying himself a new $115,000 V-12 493-horsepower Mercedes S600 ("It's pimp, so pimp!") – Timberlake checked in to one of the luxe rooms at the Trump International Hotel and Tower in Manhattan, went to see the Lakers whomp the Nets at New Jersey's Continental Airlines Arena and during the game had to deal with this older dude demanding to know if Timberlake was still seeing Spears, and what, exactly, was the story between them.

Timberlake squinted at him and said, "Do you realize how you sound right now? You're a grown-ass man – and you want to know about a twenty-one-year-old's so-called love life? Do you want me to repeat what you just said so you can know what an ass you sound like?"

The guy stuttered an apology.

"Don't be sorry," Timberlake said. "Just don't say stupid shit like that."

Being in the public eye, of course, stupid shit like this happens to Timberlake all the time, and he's learned to deal with it.

"If I was like, 'Well, people shouldn't say anything,' it would have driven me insane," he said the next day in his hotel room. "But when you know people are going to say stupid shit, you don't get emotional. I have to say something back, but I'm pretty clever, and I wait for the moment and then I make them feel dumb. By that time, the bodyguard has stepped in, and I'm on my way."

Chuckling, he moved to a window that faced Central Park. "I'm a very loving, caring person," he was saying, "and if I start dating you – you know, as a girl – it may take me a long time to give myself away to you, but once I do, that's it. You can have whatever you want. But I've had my heart broken plenty of times."

He pressed his lips together and fluttered a sad noise.

"Three times, actually," he continued. "I was fifteen the first time. She cheated on me, and I broke up with her. That's reason enough, right? 'Oops, sorry, see you.' I'd been going with her for a year. The second one I saw for a year and a half. And the third one" – and here he paused, thinking of Spears – "was for three and a half years. It was the same with her as with the first girl who broke my heart and the second. They've all gone down the same way. All of them. Three strikes, I'm out. I mean, she has a beautiful heart, but if I've lost my trust in someone, I don't think it's right for me to be with them. I'm not going to let my baggage with somebody else become my baggage with a new person. But I'll tell you, man, I have little, little hope. Three strikes. Little hope."

So that's the way it is with him. The girls he loves apparently cheat on him. It's an embarrassing thing, especially for a star of Timberlake's magnitude; but worse, it's a terrible personal tragedy, excruciating to the heart and a burden on the soul. But even that can't fully explain why he made something so publicly wounding as the "Cry Me a River" video, unless there's more to the hurt than he is fully able to admit.

After a while, Timberlake gets up from the couch, makes his way into the kitchen and begins working on his cheese steak, salad and fries. His mother is puttering around nearby and often appears out of nowhere, by her son's side. Timberlake is saying it's not as if he's not interested in other women besides Spears, because he is. He's interested in Shania Twain, for instance. "I met her in France recently, and she was wearing jeans and a low top, and she is one hot little number. Too bad she's married." And Natalie Imbruglia. "I'd like to start a rumor about me and her." And actress Shannyn Sossamon. "She's my latest crush. She just seems so unfazed. I'm scared to meet her. She's a nonconformist and looks intelligent. That makes her ten times hotter. She's too fine."

Though he claims never to have gone out with Christina Aguilera ("There was no Christina fling") and gets all coy when discussing an alleged make-out session with Janet Jackson ("A gentleman never tells," he says, tellingly), he does admit to dating Alyssa Milano. "It's still a fresh thing," he says, "and if I had to say, I'd say we are friends."

He dimples a fry into a puddle of ketchup, then lifts it into the air. "The whole girlfriend thing?" he goes on. "I'm into trying new things now. Like, I went on a date the other day. A regular date. The last time I did that, I was sixteen. It was somebody from around here. We went to dinner, came back to the house and watched a basketball game on TV. Usually, when I meet somebody, I'm always so skeptical, like, 'Why are they being so nice to me? What do they want?' But I felt I was relating to this girl on a human level. It was just fun, good twenty-one-year-old-I'm-on-a-date fun. I was like, 'This is so cool!' Actually, I think I'm in this zone where I don't want to be attached to anyone."

Then he stops talking about his date with the local girl and starts talking about Spears, though he is either unwilling, or unable, to refer to her by her name.

"When we were together it was bliss," he says, "like something from a damn fairy tale. But right now, I just don't see – it's just so hard. So hard. I'm the type of person, if I'm not exactly sure about something, then I'll wait it out and see. I may not ever get over her. That's why I'm kind of chilling. I'm waiting to see. I do have to come to the realization that I might never."

Suddenly he leans forward and says, "I think now, more than ever, everything is OK. But I still love her. I really do still love that girl."

After that, Timberlake leaves the table, goes into the other room and comes back with his Gibson, which he plays while explaining how it happened that, after much goading by the disc jockeys on Hot 97 radio in New York, he admitted to performing oral sex on Spears. "I thought, 'Well, maybe that's the sense of humor here.' But anybody who listened to that show has to know it's a joke. They were promising me spins on the radio, so I was just pimping spins. I thought it was funny as hell. That's just my sense of humor."

He returns to his guitar. Soon, his fingerpicking evolves into Kansas' "Dust in the Wind." "It's just a great song," he says, and then he begins to talk about the girls in Los Angeles and, again, his mom. "You go out to a club anywhere in L.A. and you're like, 'Damn!' But still, man, they can't hold a conversation, and if I can't do that with somebody, I really have no attraction. I want a girl who I can tell anything to and not worry about offending them. I've always been that way with my mother. We really converse well. We talk about everything, and I think I yearn for that."

Right around then, Lynn Harless, who is wearing a sweat shirt that reads be naughty, save santa the trip, comes into the kitchen and takes a seat. "I had Justin when I was twenty, and he seemed about twenty when he was born, so we've pretty much shared everything," she says, gazing at her boy. "We're weird like that. But there's a lot of stuff he starts telling me about that I tell him, 'OK, I think this is something you should talk to Trace about. Some things you are not supposed to say to your mother.' Sexual things. And his response is usually, 'Oh, Mom, just listen.' "

While his mom is saying this, Timberlake keeps on playing, smiling to himself. If, as he often says, he's looking for a woman just like the woman sitting opposite him right now, and if he thought he had found that woman in Spears, then Spears' betrayal of him must in some way feel as bad as if it were his mother betraying him. Actually, maybe nothing could be worse for a guy like timberlake, more damaging or less likely to heal.

A week later, he travels to manhattan to promote Justified on MTV, where his "Cry Me a River" video is already Number One on TRL. Timberlake steadfastly, and somewhat illogically, denies the video has anything to do with him and Spears. "I didn't make this video so I could sit around and talk about it," he says belligerently. "It's a video, and when you watch it, either you have a sense of humor or you don't. [The girl] doesn't represent anybody. She represents a female in the story line. I haven't gone public about my relationship."

He does say, however, that he's called Spears since the video's debut, "because when people blew it way out of proportion, I didn't want things to get misunderstood. She was cool. We're cool. I haven't spoken to her directly about it, because that's my career, and I don't speak with people in my personal life about my career, but I can tell you that we are cool. There's no hard feelings. What is all the fuss about? If anybody is the bad guy in the video, it's me."

And that's certainly true. If the Britney figure is a cheater, the Timberlake character is both a cheater and a creep. To exact his revenge, he breaks into his girlfriend's house, gets it on with some tramp on his girlfriend's bed, films it with his girlfriend's video camera, arranges it so his girlfriend will see the video and, upon his girlfriend's return from her own tryst, stalks her through the house and into the shower. It's weird, all right, and speaks of a guy with a mother-size hole in his heart who wants to get even and then some.

"What can I say?" Timberlake continues. "It's a good-ass video. I don't want anyone to come off smelling like roses. I don't like the smell of roses anyway."

This story is from the January 23rd, 2003 issue of Rolling Stone.

From The Archives Issue 914: January 23, 2003