I didn't really do too much bad stuff when I was a kid...
Once when I was a senior in HS, there was this nasty girl in my Cisco networking class who was a total [censored] and thought she was hot ish. So we found out what street she lived on and found her car. Well she wasn't really parked in front of one specific house and we wanted to salt her lawn in the shape of a penis. So we figured we'd just do the three houses that she was parked close to and 3 people were stuck with giant brown/black cock and balls on their front lawn.
There were certain members at a golf course I worked at that were dicks and would never want us to put their clubs on their cart for them because they were afraid we would do something. Well they should have let us, because when they weren't paying attention, we would loosen the strap that holds the bag on. When they took off, BAM, their clubs were smashed against the pavement and they were left feeling like a moron because they thought they had forgot to tighten the strap.
And the one that we used to do to people all the time was one that I'm sure many here have done. We would take a jack around to the houses of people that we didnt like and jack their car up and put boards underneath and let it back down so the wheels were about 1/2" off the ground. Usually it would take people a while to figure out WTF was going on.