When I was in high school, we were told tale of one of the best senior pranks to happen in real life. I went to a magnet school which, for the unaware, is a school with consistently failing standardized test scores that is usually in a poor neighborhood which is then given a hyperspecialized program or set of programs to entice kids who are really good at taking tests to go there. For most of my time, it was about 50-50 magnet to traditional students, which created an ecosystem of extremes. My graduating class had 185 people between traditional and magnet students, and in the first 5 years afterward we had as many people graduate from Top 50 universities as we did people who were sentenced to more than 3 years of jail time. Our football team had one of the longest and nastiest rivalries in the state and our robotics teams were all internationally ranked. My freshman year was the first time I'd ever seen somebody walk out of a testing room, and in my junior year we made custom shirts for breaking 2000 on the SAT (the max score at the time was 2400, apparently it's different now).

Our principal really tried to level with all of us in mostly the same ways. He had his work set out for him and we didn't make it easier on most days, but he also invited a bit of it. In an effort to get us to "take ownership of our school", it was decreed that no students should be cutting across the grass, especially not in the courtyard. Stepping foot off the pavement during a passing period really was like that one scene in the Princess Diaries. In general, that was whatever, but the bitch of it was that the principal had a shiny maroon golf cart with enlarged chrome rims and yellow decals (school colors, the prick) that he rode around... in the grass. To yell at people. With a megaphone.

That went over about the opposite of Coke and Mentos, so a few guys hatched a plan. County was doing roadwork about a half-mile from campus at the time, so these guys went out one morning about 5 AM and stole a backhoe. I don't know how, it varied from version to version, but my favorite was that they just got a set of keys from somewhere and drove off with it. Pulled around through the bus ramp and then got to work digging a 7-foot deep hole (little over 2 meters) in the middle of the courtyard, and then pushed the golf cart across campus into the hole and left it. Mischief managed, they started back to the construction site.

They probably could have gotten away with it, too, if not for the nature of the environment not rearing its head: There was an early morning drug bust at the corner store a block down from the school, and they all got arrested incidentally because three teenagers driving a backhoe down technically a neighborhood road at 6:30 in the morning was sketchy as shit. Admin had to wait for the summer to fix everything and it was pretty quiet for a few days in the immediate aftermath. By the time I got there, our principal was back to his bullshit, but you could wreck his whole day by asking about that golf cart.