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Remember those “Which would you rather . . . ?” games, where you’d have to choose between two equally unappealing options? For some reason, I’ll always remember this one: “Would you rather watch a porn film with your parents, or one starring your parents?” I hated those games, even though they did fit pretty well into my line of thinking. For me, every decision already consists of two wrong choices—it’s only a matter of which is the path of least regret.

But what about those situations where there are only right choices? A few weeks ago, as we were out celebrating his recent med school exam, my friend Gabe appeared to have identified one: who would I rather be, Kobe Bryant or Justin Timberlake? It was no accident, this pairing; you can’t set foot in a bar these days (at least not in Lincoln Park, Chicago) without running into the handiwork of the two on plasma screens and sound systems, often at the same time. In fact, it’s almost the perfect quandary, given that they are both heirs apparent to the world’s most famous Michaels: Bryant, the NBA’s oft-despised successor to Jordan, and Timberlake, this generation’s closest thing to Jackson.

I don’t think I ever answered the question. I won’t say it’s the wrong question to be asking…celebrity worship is nothing new, and the time to lecture would’ve been before I “borrowed” my neighbor’s US Weekly. I’ve just never really been drawn to outsized personalities like these. My taste has always been for the underappreciated stars, the ones I could somehow relate to. To this day, my favorite basketball player is Mitch Richmond, mainly because like me, he never could do much but shoot from the outside. It’s something like how guys gravitate towards Natalie Portman or some other girl-next-door-hot type celebrity—she seems attainable, even if she’s really not at all. But I realize most people allow themselves to think bigger, and why not? The Playboy Mansion would be pretty cool. So I’ll put aside my dreams of a life on the fringes, and tackle the question on every MTV and ESPN-addled mind: Kobe or JT?

1. Girls
I had a friend in high school who I’m pretty sure only learned to play guitar because it helped him impress the opposite sex. He even came up with back stories for his songs about some ex-girlfriend who cheated on him, or how he helped his little cousin learn to read (ok, I’m just mad because I never had the same success with the trumpet). It worked beautifully, of course. Girls love the sensitive musician, and they love the jock nearly as universally. Though attracting females is a less commonly accepted motivation for getting into sports than it is for music, no one grows up hoping to become A.C. Green.

Kobe has only been linked publicly to two women since high school: Vanessa Bryant (his wife since 2001) and Katelyn Faber, the then 19 year-old Colorado hotel employee who accused him of raping her. Beyond Karl Malone, who’s impressed with that list?

Timberlake, on the other hand, has the kind of history you brag to your grandkids about—you know, if you talk about that sort of thing. In addition to a close relationship with Britney Spears when she was at the height of her choreographed powers and a starring role in Janet Jackson’s wardrobe malfunction, he’s spent time with Poison Ivy goddess Alyssa Milano and Amazon woman Cameron Diaz.

This would be an open-and-shut case, except for this: About five years ago, I was driving through the suburbs of Philly with a friend, searching in vain for a dorm at Bryn Mawr College. Somehow, our trip took us right to the doorstep of Lower Merion High School, Kobe Bryant’s alma mater. As I sat there taking in the sleepy surroundings, I pictured a young Bryant, that cocky grin plastered on his face, parting the crowds during lunch period. The guy owned that school from the moment he stepped on campus, and he knew it. There could be some Chamberlain potential from junior year alone.

Still, Alyssa Milano.

Edge: Timberlake

2. Talent
On the final night of the freshman orientation program I was involved in during college, all of the counselors would perform a dance of some sort as entertainment for the incoming students.  In my first year as a counselor, we decided to model our choreography on *NSYNC’s “Dirty Pop” video. After a couple weeks of grueling 1am practices (the co-chair was a Dance minor, I think), we actually pulled it off. I’m not saying we were perfect, but at least we didn’t get laughed out of the building. My point? Dancing can be taught. Some people are more natural than others, but replicating Justin’s moves (which, arguably, have gotten a whole lot better since his days as a marionette) is possible. His voice, not as much. Dude’s got skills, no doubt—and he is showing a bit of acting prowess, too—but get a few drinks in me and I’d say I’m 65 percent there.

No one’s mistaking me for Kobe on the basketball court—just ask the teams full of angry med students who line up to play my aptly-named basketball team, the Free Agents, every Sunday evening. Every time I miss a lay-up or throw a pass into the hands of a former prep school benchwarmer, I realize how much of a gap there is between me and Kobe, a gap that no amount of practice could ever close. There’s not much he can’t do on the court, a fact even his biggest detractors have to admit. I’ve always believed the ability to dunk would drastically change my life (the large number of broken Nerf hoops in my basement is evidence of my frustration); being able to do so in traffic and over seven-footers is almost too much to ask. 

Edge: Bryant

3. Past
It’s easy to reduce a person to a two-dimensional picture that includes only his current accomplishments and standing when making a decision like this. In fact, there’s much more that makes up any life, even one filled with fame. The question is, which is worse: rape allegations or boy bands?

Actually, I think it’s more a question of what each person has done to make us forget about his worst moments. When he takes us through the book of his life, Kobe will have a lot of accomplishments to point to—he was the first guard ever drafted directly out of high school; he has three championship rings; he almost got away with hitting Manu Ginobili in the face.

Justin has a couple of platinum albums to his credit outside those *NSYNC years, but he’s also got his time as a member of the Mickey Mouse Club and a countrified appearance on Star Search to explain away. All this fits into the Michael Jackson story pretty well, rising from the ashes of child celebrity to become a serious adult star. Of course, we all know what happens in that story, and I think it’s too early to say JT’s past won’t catch up to him. You know, what goes around…

Edge: Push

4. Personality
Let’s just put it this way: Kobe won’t be hosting the Kids’ Choice awards anytime soon. Although to be fair, I hear that JT doesn’t like to look waitresses in the eye.

Edge: Timberlake

5. Lifestyle
If it’s money I’m after, there’s really no wrong choice here. Both have overflowing coffers, nice cars, and no problems securing a private jet if need be. Both also have to put in quite a bit of work for their pay: Kobe with a tough 82-game schedule, plus practices, offseason work, and endorsements; Justin with an ambitious tour, constant collaborations, appearances, and a hell of a lot of time at the tailor.

I am nothing if not a lazy man, so both of these sound like a lot to handle. But unless Phil Jackson has instituted some new rules, I don’t think Kobe gets a private dressing room. Plus, as much as I’m eager to know what really goes down on the team plane, I have a sinking feeling I’d find little more than some medium-stakes card games between Kwame Brown and Andrew Bynum (loser has to sit next to VladRad). I’d rather take my chances on a night on the town with Timbaland and T.I., thanks.

Edge: Timberlake

6. Intangibles
One of my fondest memories of freshman year of college was the quarter I spent playing Kobe Bryant’s NBA Courtside for Nintendo 64 (the last video game I was ever consistently good at) while listening to Jurassic 5’s Quality Control on repeat. Not coincidentally, this was also the worst quarter I ever had. Though Kobe might’ve been “phased out” of many of his endorsements since his legal troubles, his animated doppelganger is nothing but a perfect gentleman in my mind. Add to that his quality nickname (“Black Mamba”), and this one’s not much of a contest…until you remember the “Dick in a Box” from Saturday Night Live.

Edge: Kobe

So, it looks like Timberlake’s my choice. Hey, I was once told that I look just like him (a refreshing change from the usual chants of “Stiffler!”) so maybe this makes sense. I never could see myself in purple and gold, anyway. But I bet Justin could. I saw him take on Tim McGraw and Nelly at the 2003 celebrity All-Star Game, and it was clear he’d welcome a few Kobe moves in his repertoire; I wouldn’t be surprised if he dreams about bringing the finger roll back.  Because no matter how big you get, there’s always another level you can reach. At a certain point, though, you’ve got to realize that there’s no perfect life to aspire to, no end-all-be-all of existence, no matter what the TV tells you. You can’t be everything you want. Well, unless you’re Shaq.

Ben is a writer, editor and partly reformed music snob living near Boston. He has a website, like everyone else.

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