Here at NextRound we’ve long been mystified by Justin Timberlake.

The guy’s uncanny ability to maintain serious street cred, renowned likability, and undeniable panty dropper status despite being kind of a little bitch and the former effeminate front man of a boy band is the sort of thing that keeps us up at night.

So we decided we’d sit down with him and ask a few questions to try and clear the matter up once and for all. We imagine it went something like this:

NextRound: Justin, hey. How’s it going? Good to see you. (Attempt to shake hands.)

Justin Timberlake: What up, playas? (Morphs our gesture into complex handshake ending with a half hug. It is awkward.)

NR: Seriously dude, lose the playa stuff. We’re white guys.

JT: Oh, OK. Whatever. Just trying to keep it real…So, what did you fellas think of the big HBO special the other night? I felt really good about it. Everyone keeps telling me it was off the chain.

NR: HBO special, what HBO special?

JT: My concert special. On HBO. Last weekend.

NR: Dude, do you really expect us to sit down and watch one of your concerts on television? How long is it, like 3 hours?

JT: Something like that.

NR: That sounds brutal. Any straight guy that sat down and watched you sing and dance on television when college football was on better have gotten laid for it. If not, they have some self evaluation to do.

JT: (Silent.)

NR: What we really want to talk about is your overwhelming popularity and how the hell you manage to pull it off. We have some serious conflicting feelings on whether you should be considered cool or not. For starters, there’s the pop music and dancing stuff that we’re pretty much against, but then you do stuff like “Dick in a Box”, which we are all for. And then there’s the whole “JT Theory”, which is such a strange phenomenon because it’s kind of cool yet bullshit at the same time, but…

JT: What “JT Theory”?

NR: You know, the theory about how you leave all the chicks you date mangled and ravaged and shells of their former selves. Like how Britney became a tub of white trash cheeto eating goo after you finished with her.

JT: Yeah, she has been hurting. But I don’t know that has anything to do with me. What about Cameron? Same can’t be said about her.

NR: Are you fucking kidding? If anything, she was beat down and past her prime before you got with her. What the hell were you thinking anyway? You squandered like three years of your ass-closing prime to hang out with that creepy old bag. What a shame. Please tell us you two weren’t exclusive and you were able to take advantage of what a lucky bastard you are.

JT: No. I never cheated on her. She meant a lot to me.

NR: Dude, that is weak. That’s about as weak as being in a boy band. (Chuckle to ourselves.) Speaking of being in a boy band, did you have that part of your life just completely singed from your memory? Can those other guys even look you in the eye anymore? Bet they can’t. Well, Lance Bass probably can. They must have all drank themselves into a coma watching your HBO special.

JT: We’re actually all still really close. They’re great friends. I support them in their own personal endeavors. They’re some really talented guys.

NR: C’mon. Can the bullshit. You were carrying those guys and you know it. You might as well have just set up trust funds for them. You know it’s true. Admit it.

JT: Well, there’s probably a little truth to that…

NR: Holy shit! We didn’t think you’d actually admit that. Wow. That’s a pretty self important claim you just made.

JT: Hey, wait…

NR: Man, that’s kind of bullshit that you’d go and crap on your old band like that. Especially to some dudes from a subpar website. Doesn’t that break some band code? Even if it is a no-talent boy band who doesn’t really fill the requirements of an actual band. You better watch out. You’re in line for a Lance Bass eye gouge the next time you see him.

JT: C’mon, that’s ridiculous. You’re putting words in my mouth.

NR: Don’t worry about it. We won’t tell anyone. Back to some more serious questions. Was Diaz just a minx in the sack or something? Or did she just perpetually rufee you? We can’t get our heads around that whole debacle. We get the whole Britney thing. She was the tits a few years ago. And we definitely get Jessica Biel. Now that is a respectable accomplishment. Give us some details on that one. You’re not planning on ruining her too are you?

JT: Man, get over the Cameron thing. It was what it was. And as far as Jessica goes, things are going well, but I’d rather not comment.

NR: Do you ever just wake up next to Biel and have to resist the urge of snapping camera phone shots to send to your buddies with captions like “Another one bites the dust” or “One way ticket to Poundtown”?

JT: No.

NR: Yeah, well, with buddies like Lance Bass guess that’s not much of an option. OK, next question. There’s no way that you’re 6′1″. We read that somewhere. We’re guessing you’re more like 5′7″, a buck forty. You wouldn’t be remotely intimidating if we passed you on the street.

JT: I’m 6′1″, 180.

NR: No way. Stand up. (We stand up.)

JT: This is fucking stupid. (Stands up. Is exact same height.)

NR: (Pissed off that JT is same height. Look down at JT’s shoes.) Dude, those stilettos you’re wearing add like ten inches. Take ‘em off.

JT: No way. This is the dumbest shit ever. (Sits down.)

NR: OK then. Fine. We stick with our 5′7″ assessment.

JT: Whatever. Do you guys have anything else you want to talk about? I’ve got some places I’ve got to be.

NR: We can’t let you leave without asking you about the whole Janet Jackson thing.

JT: What about it?

NR: How about how fucking gross it was. We totally agree that you must not have known about her having nothing on under there, because nobody would have put themselves in that close of a vicinity with such a gnarled nipple. How’d you keep yourself from vomiting or having a panic attack?

JT: It’s all kind of a blur.

NR: We buy that. It probably goes into your vault of vanquished memories where you keep the N Sync days.

JT: Yeah, whatever. Seriously, I got to go. I’ll catch you fellas later.

NR: Sure thing, playa. (Slap hands with JT). One. (Butt chests.)

JT: (Confused.) Playa?

NR: Just fucking with you. We would never talk like that. You keep it up though. Seems to be good for your street cred. And just so you know, you’re coolness is still up in the air with us. We’ll reevaluate again in ‘08.

JT: Thanks. I think. (Walking away.)

NR: And do us a favor. Tell Biel we said that next time we’ll be ready to commit. She’ll understand.

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