I realized recently that I don't know what "cool" is anymore. Remember when you were in middle school/high school, how concerns about "being cool" took up a disproportionately large share of your mental energy? Now I don't even care about being cool, if only because I don't know what it is anymore. I have no benchmark to shoot for. No northern star to guide me. My thoughts on the current "being cool" situation can best be summed up in two points:
1. Everyone who I think is cool is to some extent (or at least once was) a dork.
2. Everyone else is boring.
Let's look at some real-world examples. Justin Timberlake is probably the coolest guy I can think of. If I could be one other man, it would be Justin Timberlake. But Justin is clearly a dork. If anything, he sings and dances for a living.
Will Smith is another person I think is cool...but he makes way too many sci fi movies to not be a dork. And his rapping? My god, his rapping!
Vince Vaughn could be cool, except he's not particularly attractive. You must be attractive to be cool. Also, he was clearly a slacker. Carefree, relaxed attitude = cool. "I don't give a shit that I'm a loser" = not cool.
Johnny Depp is actually one of my favorite examples. Everyone thinks he's so sexy and mysterious now, but if you'd met him in high school you definitely would have thought he was a weirdo. He's one of those kids the teachers would have kept their eye on after Columbine.
Rock stars are dorks. So are comedians. So let's look at the flip side. YM tells me Chad Michael Murray is cool, but he's clearly a fucking douche. Ditto on Cameron Diaz...and she's not even close to being hot enough to get away with it. Basically the only people who have even a shot at being cool are pro athletes, and athletes aren't cool. They're idiots. Even the smart ones. Take Tom Brady. Very successful QB, my female friends tell me he's attractive (or at least my ex-girlfriend does, which is always a nice conversation). But listen to Tom Brady talk. He's dull. He's boring. I wouldn't want to hang out with him.
In the end, George Clooney is probably the only truly cool person I can think of. He's handsome, he's successful, and he's also clearly intelligent. Matt Damon too, possibly. But that's it. Two guys in the entire world. What's the point of trying to be cool if those are the kind of odds you face?
And now for...An Anecdote from High School: I think part of the problem is that being cool is ultimately relative. In high school it works because you're in a small pond with delineated boundaries and a determinable hierarchy. But in the real world it's too much, it's a free-for-all.
Example: I remember in high school going to this party being held by what was in my opinion the coolest girl in the school and (at the time) pretty much ever. But as I was walking up to her door there were these three dudes from another high school in front of me who were essentially crashing the party. They were also sneering amongst themselves that her party was "so middle school." I actually had some interesting mental responses to this comment:
Nerdy Part of Me: "Are you serious? Do you even know who's house this is? This is the coolest girl in the school!"
Mature Part of Me: "If you think it's so lame, why don't you leave? It's not like anybody wants you here."
Rage-Filled (aka my Default) Part of Me: This part didn't so much have an actual comment as a desire to punch them one-by-one in the throat. Okay, that would have been an overreaction.
Anyway, the point is, here was in my opinion the girl who symbolized the epitome of cool, and these kids thought she was lame. But they were, at the least, also lame. Cool kids don't crash parties they think are lame. Obi-wan Kenobi inquires: "Who's more foolish - the fool or the fool who follows him?"
The fact that I can recite that quote makes me cool.