I can remember the exact moment I decided to be cool, because it was a real moment, one of those innocuous little interactions out of life’s countless multitude that sticks in your gut; a secular ebenezer.

Shortly before a girl I was very into dumped me, we were listening to the White Stripes and Jack yelped one of those immense, inarticulate yaps of his and I saw her face visibly redden, to the point where she apologized.

“Sorry,” she said. “But that’s sexy.”

She didn’t have to apologize. I had no delusions about being as cool as Jack White then (I do now), but when she left me shortly thereafter, that comment about him stood out.

You can control so few things in life. You can’t control who will love you, and how long they’ll love you for.

But you can control how cool you are. At the very least, I was bound and determined to try.

* * *

Everyone has different ideas of cool, but there are a few objective standards. The most obvious of the league of White American Cool Guys is James Dean.

When Dean was nine, his mother died and he was taken under the wing of a minister with an uncharacteristically badass taste for bullfighting and car racing (rumors that the pastor’s relationship with Dean may have been inappropriate were never confirmed). Dean dropped out of college to pursue acting and after a few small walk-on roles landed three: East of Eden, Rebel Without a Cause and Giant. That was it. He was 24 when he was killed in an auto racing accident.

Perhaps no actor has cast a longer shadow with such a smaller body of work. East of Eden put him in the company of Hollywood’s elite (and made a fan out of John Steinbeck, no stranger to cool himself). Giant, released posthumously, won him an Oscar. But in truth, all he needed to become a legend was Rebel Without a Cause, one of the first films to attempt to articulate the alienation of adolescence, and the only to do so purely on the shoulders of James Dean.

It retrospect, nearly every trick Dean used was used first by Marlon Brando. Both discovered the camera and the public went into a tizzy over their coiffed hair. Both had a practiced, perfect pout that, when paired with a slouch, made them irresistible. Both learned to work their cigarettes like a joystick for the lusty gazes of onlookers.

The only thing Dean pulled off that Brando couldn’t is dying young and beautiful.

* * *

The hardest part about becoming cool is, of course, as soon as it looks like you’re trying, the gig is up. There are few sights more ghastly than someone trying to be cool. The trick is to practice in secret—the disaffected slouch, the wry grin and the devil-may-care flip of the cigarette-and then let it out like you’ve been doing it all your life.

I started slow, just in case. If I was doomed to fall, I wanted it to be a short fall. I knew I wasn’t a rock star (no rhythm) or a rebel (too responsible) but I found a few things I could do that people seemed impressed by—a taste for neat whiskey, an ease with girls and, most importantly, a way to project my insecurities into an approximation of the wounded loner. It was truer than I knew.

Cool? I don’t honestly know, now. I don’t think so. But it came at a cost, I can tell you that.

* * *
Actors can be very cool but cool has always been the realm of rock and roll. Dean may have invented the bad boy pout, but who wore it better than Elvis? Brando’s slouch suggested a mysterious brooder, but the way Bob Dylan sunk into his frame made everyone around him seem unworthy of his presence. And I’d go into Springsteen here, but I’ve written about him enough, I think.

And this without going into the all-American, self-destructive machismo of Lou Reed and Ernest Hemingway. Or the buttoned-up autonomy of Don Draper and Fred Astaire. You can be rich (Sinatra) or poor (Kerouac) but you absolutely can not be in between. You can be pretty smart (Ginsberg) or pretty dumb (most of them) but you can’t be too far into either extreme.

It is not very hard to be a white man in America. At least, it is easier than any other demographic.

But it’s very hard to be a cool white man in America. Only because there are so many of us. And almost all of us are not cool. And we know it.

* * *
My years as a brooding loner were mercifully short. Whatever credit they may have earned with me with the opposite sex were checked in that, as a number of girls said, I was impossible to get to know. I locked them out, shut up my emotions and kept them at arm’s length.

You know, typical cool guy stuff.

I am not surprised at that. I hardly knew myself.

It’s because I had an act, and if anyone did get to know me, I knew what would become of my carefully studied cool.

I would be unmasked.

I’d be found out.

I’d be the same boy who got told “Sorry, but he’s sexy!” by a pretty blonde I hadn’t seen in decades.

Being cool—my approximation of cool—came at the cost of distance. I paid it.

We all do, in our ways.

* * *

Cool is perishable. Its shelf life is shorter than you think. Nobody’s maintained it without fail their entire life (although, if left unused on a shelf for a few decades, it appears you can dust it off and put it to good use. See Downey, Robert Jr.).

There are, it appears, three options for what to do with cool, and I’ve named them all.

The Brando: Spend it in your youth and live out the rest of your days in abject uncoolness.

The Dean: Die young and be cool, forever.

Trade it in for intimacy.

I’m thinking of calling this one The Huckabee, but not just yet.