my senior year we went to the neighboring high school, Edison, and we spray painted the living crap out of their football weight room. We brought like 40 spray cans and like 12 one gallon tubs of paint with brushes.
We also went into their little center "quad" area and cut down a big tree using an axe.
The same night, some other group of kids (waterpolo i think) put a dead cow's head in their pool. It turned the water kind of pink.
In return they bleached our baseball in field with all sorts of vulgarities 2 days before the game so they showed up on game day.
We had some good rounds with that school.
At the last Varsity basketball game of senior year, the team being played were long time rivals. Some guys from my class went into their locker room during the gane and poured some sort of acid on their clothes. Unfortunately, when our janitor went to clean it up, he threw clorox on it and it ended up creating a gas cloud. He passed out and almost died. It was a huge deal. The administration made threats, but no one ever fessed up.
Actually, on the last day of school, I brought water balloons to school and the seniors went nuts on the freshmen. Actually, some friends of mine and I were throwing them in the freshmens cars. A couple of guys had to replace their CD players. A few weeks into the summer break everyone got letters asking them to apologize and pay for the damages. I never got a letter. No one believed I was involved. Actually, I never got in trouble; but I did more than most people. I was lucky back then I suppose.