So now we know. In case you missed the news, literary archaeologists have unearthed the evidence, more earthshaking and culture-shocking than any suppressed scroll Dan Brown could dream up. Jack Kerouac -- Mr. On the Road, the King of the Beats, who begat the beatniks who begat the hippies who begat the hipsters -- Jack Kerouac, the fountainhead of cool -- that Jack Kerouac was obsessed with -- guess what. Freedom? Alienation? Restless, rootless wandering? Mad pursuit of the beatific vision? Nope. Jack Kerouac's deepest-rooted, longest-lasting obsession was ... fantasy baseball.
How obsessed was he? So obsessed that, years before fantasy baseball existed, he invented his own version of the game, with whole teams and leagues named for colors and makes of cars, and series and seasons played out with marbles for balls and toothpicks and matchsticks for bats. So obsessed that he filled notebooks with meticulously recorded stats, made illustrated team rosters, and wrote letters back and forth between his various team-managerial personae, haggling over trades. So obsessed that he persisted in this childhood hobby through all his on-the-roading and dharma-bumming, through obscurity and fame and alcoholic decay, almost till his death. So obsessed that he concealed his decidedly uncool secret from all but one or two of his aspiringly cool fellow Beats.

I guess we should have known when we found out that Marlon Brando was a ham radio operator. What next? Any day now we'll probably learn that James Dean collected stamps, that Lou Reed and Andy Warhol traded Matchbox Cars, that Miles Davis's real passion was his model trains, which he ran while wearing an engineer's cap.
Mr. Cool, the guy who started it all, was a geek. And if Kerouac's not cool, nobody's cool. What a relief! We can just relax and be ourselves. (That would be ... cool?)
Of course, Kerouac didn't really start it all. He got the cool thing from jazz musicians, hanging around the 52nd Street nightclubs during his brief stint as a benched football player at Columbia, transforming the laid-back-even-when-frantic rhythm of bebop -- the beat -- into Beat Generation prose, writing lovely poetic tributes to Charlie Parker's Buddha-eyes.
If anyone started it, it was Prez, Lester Young, half a generation before Parker. Somehow lightening and purifying the gutbucket sound of the tenor sax till it sang like an alto, Prez used that cooled-out voice to slice through the overheated busyness of early jazz, unhurriedly hanging behind the beat or somehow mysteriously hovering above it, in an ever-cool, rarefied realm not touchable by the mundane world of 4/4. And just incidentally, Prez appears to have been the first person to wear sunglasses as a cool fashion statement; he may even have coined the word "cool" as a term of approval.
Interesting word, actually. In physics, that which is cool is that which exhibits less random molecular activity -- that which is more settled. Maybe real cool, the essence of cool, is inner cool, settled awareness, buddha mind, the nirvanic state.
In that case, we can amend our statement. Nobody's cool but those who have stopped shaking and stirring this jar of muddy water called the mind long enough so that the mud can settle and the water's natural clarity can shine forth. That is, nobody's cool but buddhas. Note that I didn't say Buddhists: buddhas can be Christians, atheists, Hindus, or Venusians. (And Buddhists can be buddhas or knuckleheads like anyone else.)
But cool as an outer pose -- as a book or an outfit you can buy, as an attitude you can cop -- is dead. Long live cool. When the truly cool people show up in your life, you won't recognize them -- they'll be too cool for that.

I attempt to point out that they are so far from cool it isn't funny.
I rent him "Revenge of the Nerds" to show that qualities like talent, interests, intellectual ability, friendship, inclusion and individuality are cooler than whatever 13 year old snot noses currently think is cool.
He gets the message. I live in hope.
I have heard it suggested that Kerouac and company sought Pres' disaffection. That is the source of their being uncool, trying to affect something they never could have been.
the person on the street is seldom seen by others...it pays to stop and get to know people, that's a good start to finding cool people and the first step to being cool yourself.
if i say cool again, take my puter away.
OTOH, there is coolness in degrees. Being a deadbeat husband and father and killing yourself with alcohol for no good reason is not cool.
But when I think of cool it's in your statement of not having to wear it,or a that sax players solo intro say to "Turn the Page",Cannonball Adderly's "Mercy Mercy Mercy" being played when you walk into the club and your name being announced.And Dean cool is how you put this magic gift we find between the spaces and I come to read things like the "Zen Commandments" again for the 5th time as a way of practicing the Dharma or "The Why the Chicken Crossed the Road".We all know that chicken was trying to be cool doing the funky chicken.Thanks for your gift.Some folks are just cool they are born with it.They call the genetic cool pool:)
um — posing as cool was never cool.
i think it's interesting that there are so many articles this week about kerouac's invention of fantasy baseball — part of being cool is not going into the details, even though you know them. people who know kerouac's writing have been aware of his obsession with statistics for decades — that information is contained in works that have already been published.
kerouac was an observer of cool. i dont think he would have ever considered himself cool. he wasnt dean moriarty. he was barely even sal paradise! kerouac's cool was in his writing, which happens to have included his identity as a huge baseball fan.