Setting his/her school on fire as a kid, or returning to it as an adult to set it on fire (probably while empty as killing a school's worth of children is a bit too unbelievably evil).
Slashing tires
Using the sidewalk as a shortcut for cars
Putting cigarettes out in people's hair
Going around placing small explosives (like cherry bombs) in just about every conceivable place: mail boxes, trash cans, toilets, pipes, chimneys, people's pockets.
Pick pocketing and after taking their wallet, leaving a nasty note behind.
Blowing up a car, no country for old men style
And if he wants to go to jail: Driving a car into the front of the police station while flipping off the world.
Edit: ooh, also stealing traffic signs, breaking traffic lights and moving traffic cones, nothing syays pure chaos like a 7 car pileup.