You know why Jack Kerouac was cool? Because he had no idea he was.
Now, I don't want to get off on a rant here, but cool is a gift. It's having eight pounds of hip in a five-pound bucket. It's not bought, bred or bequeathed. Clinton lost it, Gore can't buy it and Bush thinks it's spelled with a "k."
America's drive to be cool is like an endless game of "Follow the Leader," with all of us in a dog-sled-train, struggling to keep up with the alpha male trendsetter, when all we can make out are the hazy, glistening outlines of his ice-flecked, rhythmically pumping butt cheeks. Sorry, I got a little carried away, there. I'm still recovering from Gay Week on Animal Planet.
The United States is the birthplace of cool. If the world was a high school, America would be making out in study hall with Sweden, picking on India, and smoking in the U.N. restroom with France and Colombia.
Coolness appeals to us because it represents being free from the constraints of society while still living within it, dropping in to give Richie and Chachi a dose of hard-earned street wisdom, and then headin' off to Arnold's to grab a shake and pound a free song out of the jukebox when the Cunningham scene gets a little too "square." By the way, almost triggering a petite mal seizure by doing the finger quotes thing - uncool.
Now, there are many types of cool. There's the classic, iconic, Bogart approach: cryptic and unflappable, squinting through the smoke from the cigarette dangling between your lips, never letting a trace of emotion show except for an occasional sardonic half-smile at the foolish world around you that you couldn't give a rat's ass about.
As a matter of fact, some celebrities reach a cool of such mythic proportions, it transcends their physical being. Frank Sinatra is so cool, he hasn't bothered to take a breath for years, and he could still kick the shit out of you.
Then there's the demographically researched, pop-media faux-cool, the type of insouciance that bears the corporate patina of mass-marketed nonconformity. This is shopping mall cool, easily attainable: You don't have to Harley to Sturges; or Master the Guitar; or Trek through Nepal-- just plunk down your Discover card and buy some threads at Urban Outfitters or a barbed-wire bicep-tattoo at the Henna Hut, and not only will you enter the kingdom of cool, you'll also get a valuable cash-back bonus that can be applied to cruise travel or a Reader's Digest subscription.
I think some manufacturers may be trying a little too hard to envelop everything with a hip aura. I was at a drug store and watched an old man spend 15 minutes trying to decide if he wanted his Ex-Lax in Extreme Orange or Totally Wacked Wintermint.
There are certain places and situations where it's virtually impossible to put up a cool front. For example, when your doctor gives you a prostate exam, or when the supermarket cashier calls for a price check on super-small-size condoms, or when the door man at the Vanity Fair Oscar party bitch-slaps you for bursting into tears when he tells you he can't find your name on the guest list, even though it should have been there it SHOULD HAVE BEEN THERE!! J-Lo, I love you!
I guess the coolest I ever felt was when Carveys Church Lady was really taking off on Saturday Night Live, and yet the entire nation was doing my George Bush impersonation. Oh wait, that was Dana, too. Come to think of it, I've never felt cool.
One of my favorite pastimes is to look around and try to determine who the coolest person in the room is. For example the other day at Starbucks, as I observed the 20-something counter jockey with the pierced prefrontal cortex and the dust bunny on his chin, and the as-yet un-produced screenwriter sitting in the corner staring at a four-year-old script-in-progress that still has fewer words in it than his latte order, or the heavily perfumed walking designer rack talking into her cell phone like she was trying to be heard over a fucking chainsaw, I realized with some pride that I could honestly say I was the coolest person in the immediate proximity, until I looked out the window and caught the eye of the Guatemalan landscaper trimming the hedges outside, obviously wondering what kind of schmuck I was to pay three dollars and seventy five cents for a cup of coffee.
Let's bottom line this. For me, the only real cool people left are those who don't buy into the coolness mystique. People who dont take themselves too seriously and don't screw over other people and understand that life goes on, the earth abideth forever, and what is cool today may not be cool tomorrow. That's why it's best just to be yourself. You know, unless, of course, you're an asshole.
Of course, that's just my opinion. I could be wrong.