I used to be what might be considered cool and hip, or at least I hung out with people who most certainly considered themselves cool and hip. Basically it seems to me to consist of taking lots of drugs, listening to music nobody else has heard of, and spending all you're money on going out to parties.
Anyway if you get involved with those types of crowds it can all seem pretty exciting for a while but evenutually it becomes apperant that it's only about trying to impress people and convince them of how cool you are to avoid dealing with those insecurities. I don't really regret hanging around witht these people, I had some fun times and a lot of them were good people who I still consider friends, but it's a very shallow, fickle world and I'm a lot happier being boring and just having a couple of friends.
Also efforts to seem cool often result in people being very stupid. Case in point I went round to one of those old friends houses not so long ago, on a saturday afternoon, to see if they wanted to do something. They'd been up all night and were in the kitchen trying to turn coke into crack using baking soda, just so they could tell people how funny and daring they are.
People who understand there not cool are much more sensible