What's wrong with being "cool"?

Short answer, is "nothing" I suppose. The longer answer is that there is something more I am looking for.

If you check the earliest reference books on slang, you will find that the word "cool" does not appear.

It comes in later and right from the beginning there is a drug association with cool. My first experience with coolness was in high school.

Here is how it would work. You'd go somewhere—a trip to the Stratford Shakespeare festival, for example—and find yourself surrounded by a group of people from other high schools, people you didn't know. And pretty soon you'd see some people starting to work their way around. They had this combination of boldness and paranoia about them. They were the dope smokers in the crowd and they were looking for others. Separated from the circle they knew, they were looking for a new circle to buy and share dope with.

It was touchy business for them. On the one hand, they had no interest in getting stoned alone. On the other hand, they could get in trouble with the teachers or even arrested. Someone cool was someone who could be part of this. It was never particularly social it was about fear of being alone and fear of getting caught.

The not aloneness was never particularly about friendship. The alacrity with which dopers will sell out other dopers has always been and remains astounding. To repeat, it was quite simply about not wanting to be alone. It was driven by a deep fear of being alone.

Here is another example of how it worked. When you went to buy dope in the late 1970s, you were expected to light up some of what you had just bought and share it with the dealer. This was meant to display your good faith. It was assumed that no undercover officer would do this. Plus dope dealers were lonely losers and didn't have many friends. Finally, they were con men always looking to get more out of you. All of that made them put this odd pressure on you not to leave.

It was this sort of nonsense that saved me from getting very heavily involved in the dope scene at my high school (probably the single largest cultural influence at that not-terribly-august institution).

BTW: A joke that sums up my experience;

Q: Did you ever try any of the hard stuff?
A: No, we always got someone else to roll them.

Anyway, cool will always mean lonely loser. It will always mean some druggie like Chet Baker selling out his wife to score. Or it will always mean someone, maybe a good person at one time but no longer, who didn't so much fail at love but always held back a little bit and never made it work. No matter where you find coolness, it always come wrapped in fear.

The thing I am looking for isn't that. Cool isn't a virtue.