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Justin Timberlake, The Bachelor

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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.

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Song Stories

“Try a Little Tenderness”

Otis Redding | 1966

This pop standard had been previously recorded by dozens of artists, including by Bing Crosby 33 years before Otis Redding, who usually wrote his own songs, cut it. It was actually Sam Cooke’s 1964 take, which Redding’s manager played for Otis, that inspired the initially reluctant singer to take on the song. Isaac Hayes, then working as Stax Records’ in-house producer, handled the arrangement, and Booker T. and the MG’s were the backing band. Redding’s soulful version begins quite slowly and tenderly itself before mounting into a rousing, almost religious “You’ve gotta hold her, squeeze her …” climax. “I did that damn song you told me to do,” Redding told his manager. “It’s a brand new song now.”

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