Graduated class of '91. There were 103 of us (~550 in the school, my year was the smallest by far). 'Cool' is in the eye of the beholder, right? To my small group of friends, maybe I had some degree of coolness. To everyone else, probably not. I lived in a farming town and commuted 40 miles each way everyday to an all-boys (Jesuit) high school in the city. Not difficult to see where I was not part of the in-crowd. That being said, there wasn't a lot of attitude in my class and I honestly got along with everyone. By senior year I had had conversations with everyone at some point. I did not go to parties (too far and not much interest), did well grades-wise, played some basketball, and finished less naive and very prepared academically for college.
Am I cool now? I suspect most people would say no, but I'm happy so who cares? Family, friends, dogs, woodworking, motorcycles, pipes, cigars, good scotch, Jack&Coke, and great dark beer make the days good ones most of the time.