habitual line stepper
A person who goes over the line so much it becomes a sport. They don't care about getting kicked out, fined, or told they're a disgrace.
He went over the line at the party and started a dance-off with the cop. Nobody won, but everyone laughed.
She went over the line at school and tried to steal the teacher’s lunch. I had to stop her with a spoon.
He went over the line at the store and tried to take the last candy bar. I had to hold him back with a shopping cart.