Note: This is another one of those email conversation things. See also The Nineties.


I was driving home yesterday (ed. note: “yesterday” was about 3 months ago), and the thought occurred to me, “who is the coolest person alive today?” I’m not sure what brought this to mind, but it made me wonder if it’s really possible to be cool anymore. I think coolness requires a certain amount of mystery, and, with the blogonet and the intersphere, it’s nigh impossible to remain mysterious. Also, the instant anything cool or noteworthy happens, there are about 1,000 people waiting to deconstruct it or make parodies of it and tell you why it isn’t really that cool, and, in fact, is the lamest (see my previous comment about “fake” and whatnot).

Anyway, who is the coolest person alive today? Here are a few candidates provided upon minimal reflection:

1. Jack White. He’s been the driving force between three very different but successful bands. He has some definite mystery with the whole Meg White sister-wife weirdness and what with looking undead and all. See also Dave Grohl and Julian Casablancas

2. Banksy — very mysterious and came off as about the coolest guy ever in Exit Through the Gift Shop, though there is the haunting feeling that Exit Through the Gift Shop was just a vehicle to make him look cool and mysterious.

3. Paul Newman — yes, he’s dead, but he’s also Cool Hand Luke.

4. Every character in The Wire. Except Ziggy. He was the worst.

5. The Situation. Ha ha! I don’t even know what that means.

“No coolo.”

Are there any current athletes or actors that qualify? None come to mind for me. I’m afraid I know the answer and that the answer is Jay-Z, but, if that is true, can anyone explain the allure of Jay-Z to me? He seems like a really boring guy to me. What am I missing? I haven’t really listened to his music that much, but the little I’ve heard was just boring. And nothing I’ve seen of his fashion strikes me as compelling. I mean Snoop in the 90’s was cool. You could say the same for Tupac and, I guess, Biggie, though I confess ignorance when it comes to him. Even Eminem had something about him that you couldn’t turn away from, something that was compelling as hell. Other than the fact that he sits next to Beyonce, Jay-Z doesn’t hold my interest at all.

What say you?


There’s a great moment in the movie 500 Days of Summer when the lead character looks into a mirror and the reflection looking back at him is Han Solo. This happens when the character sees himself at his highest/coolest point. I laughed out loud the first time I saw it. I think I believed I was the only one who felt this way about Han, but Mrs. Wheat confirms that every white male of my generation thinks the same. Although some might say they are basically the same character, Indiana Jones is just as cool as Han Solo. But Harrison Ford is not necessarily able to take this off of the screen and into real life. I still can’t get over the earring.

Hold on a second, I need to put on some music for inspiration. For those of you listening along at home, try some John Coltrane, “My Favorite Things.” I will wait for you to start it. Ready? Now FEEL it. Wait for John to come in. Nice, right? Now this is cool.

Why is it so cool? For one thing it seems easy. He’s playing one of the most well known songs in the United States. And he is literally playing with it, taking the melody to places that curtain dresses never dreamed of. So it is new and fluid and yet familiar and timeless. A person/character who is cool to me achieves the status in much the same way.

This ease, this being comfortable in my own skin is essential. There are only so many roles that a person can play. We come to know the roles intimately early on in life and categorize people into them without making conscious decisions. So when someone comes along that either exemplifies the role or tweaks it in a subtle way, then they become cool. People are drawn to him/her whether the individual wants them to be there or not. I agree the mystery is a part of it, but there are times when what is cool is so obvious that it becomes a mystery how the person can be so successful with it.

Also I think there is an unattainability that has to be associated with cool. Remember how cool the older kids were, but when you reached that age it was no longer that big a deal. There is always a peak beyond in order to climb for the ephemeral being of cool. I envy young black men with their hair grown out a bit on top, then worked it into together into simple twirls. This style looks so chic. Anytime I see a man with this hairstyle, then he is immediately cool to me, no questions asked. But the reason that I envy it at some level is that I can never look that way. Frankly, you can never underestimate hairstyle when evaluating coolness.

However, if you are pressing me to define the coolest character or person that I know, then I think of Coach Eric Taylor and Tim Riggins from Friday Night Lights or George Clooney, and even Steve Jobs-all for very different reasons. I also understand that at some level all of these choices are fictional.

Texas Forever

Beyond those I think of my older son, Jamison. At four years old, he fits all the qualities. People love him without exception. They are drawn to him, and he repays with easy acknowledgements of hugs and smiles. He remembers names and what people’s interests are. He is a mystery to me much of the time confounding me in ways that both frustrate and amaze. He has something I will never have—youth. And he has good head of straw hair. Mostly though I think of him because he calls himself a “cool guy” and makes strange faces when his mother tries to take his picture.


Ahhh cool. It’s not cold, it’s not hot, it’s not extreme, it’s not tepid, it’s just nice – real nice. Cool breeze, cool under pressure, cool as a cucumber. There was a period in time when a tune might be really “hot” and that would be a good thing, although since an extreme modifier might be seen as a complete vote of confidence we now bestow our high praise in the most temperate way. I remember when the youth culture first wanted to counter what those old fuddy duds were saying by calling good bad, as in MJ’s importal question, “Who’s bad?” Boy, was that a confusing time.

I agree with Wheat and Water (on so many things really). Cool is unatainable and effortless and understated all at once. In fact, the word cool itself is probably too much of an overstatement for the coolest person in the world. It might be better to call him interesting.

…enter the most interesting man in the world. This idea was a stroke of genius on the part of Dos Equis advertising. This guy is subtle, laid back, has done impossibly awesome things (while always speaking of them as though they were merely interesting) and he is infallible – because he is fictional. Oh, and he has a rocking beard. If they were to pick a living, breathing athelete to endorse their product then we’d just find out about some raunchy sex scandal a few months later. And of course the finishing touch for this imagined icon of coolness is that not only does he not garner the highest endorsement (of being the coolest), but he doesn’t give it either. “I don’t always drink beer, but when I do I drink Dos Equis.” Well isn’t that a rave review.

“I don’t always read blogs, but when I do, I prefer The Basiks.”

It would be all to easy to pick a fictional character, because he would never never gush, grimace, or guffaw, no matter how lavish the praise, dire the situation, or funny the joke. If we were to passionately confess our love before he is slowly lowered into the carbonite he would only say, “I know.” So I will cast my vote on one who has a mortal coil and has not yet thrown it off. Wheat went for the youth vote, but as my nod to the most interesting man in the world might suggest I’m going to pay some respect to my elders.


Not only does this 91 year old Hungarian grandmother look pretty great in KISS make-up and a cape, but she also has a mysace account with a bazillion friends. Could a bazillion people on Myspace be wrong?! While she has a wry since of humor in the darkest of times (cool), and can apparently get her hair done while wearing a crash helmet (cooler), she also risked her life by saving ten people from the Nazi’s during WWII (coolest). Sadly Mamika is not my grandmother, but then again, I never asked my grandmother how many people she saved and I never saw her sport a cape, so I can’t be quite sure. The coolest person in the world would never vaunt his (or her) virtues, because that would be so passe. So I think if we look for the alter ego of Mamika amongst the venerable around us we just might unmask the coolest person in the world.


Did I mention sunglasses? Nothing’s cooler than the right pair of shades.


So we’re agreed that Jay-Z is a no, then?

Have we derived any basic principles of coolness that dorks such as ourselves can apply in our daily lives? A couple of common themes I’ve noticed are (1) being comfortable in your own skin, (2) making the difficult seem easy, and (3) a sense of style or grace. I think this is interesting, because to have a sense of style, you have to put thought into what you wear or what you do, but you don’t want to make it look like you put thought into it. I’m reminded of my friend Matt, who’s a very cool guy, and who used to spend, like, two hours meticulously fixing up his hair to make it look like he had just gotten out of bed. Bizarre, but he made it work.

Based on these criteria, and, though it hurts me to say so, I’m going to award the coolest guy on earth award to:

Derek Jeter

I assume the list of women Derek Jeter has dated will be included on his Hall of Fame plaque.

Cool under pressure. The most graceful and stylish Yankee since DiMaggio, and does anyone seem happier being who they are than Derek Jeter does?

And if you disagree, my two word response is: Minka Kelly.