Fine people who are double parked, and believe that they shouldn't be subject to the rules of having to schlep shopping bags full of groceries ( or whatever ) out to their spot on the lot, or street, and so blocking a lane instead.
Fine people making a big racket in places that are traditionally associated with being quiet refuges, like libraries, or bookstore reading nooks.
Fine people who act as speed limit enforcers in the fast lane by driving slowly there.
Consider humiliation as a punishment for some criminals, versus making them stay in a confined space for awhile.
Take all the people in cushy jobs who write columns on "Careers" for the local newspapers, and who offer such cutting edge advice gems as "try to work things out with your boss, versus openly complaining or going to HR", or "It's best to match your career with your interests and abilities" and throw them into a pit together where for two weeks they must struggle with one another for scraps.
Force infomercial people to use their own products, and make Billy Mays listen to a tape loop of his commercials at higher than usual volume over and over. Over and over. People with obnoxiously folksy voices used on ads will be forced to listen to ice cream truck jingles for days on end.
Make news program strategists chase after a car holding keys to handcuffs they are forced to wear, or via some other incentive. Let them think they are getting close to the car, and then move it a ways down the road, like the teasers they use to make one stay tuned in to their mostly insipid programs.
Gather school bullies together in a ring and make them fight one another for the pleasure of the crowd, who were formerly tormented by them. There won't be a strenuous effort made to make sure the bullies are evenly matched, and in some cases it will be a donnybrook of many people. ( I've always wanted to use "donnybrook" in a sentence. )
Place all the people whose standard response to people wanting change is to use the word "whining" and put them in jobs with contradictory demands that cannot be questioned due to the "politics" of being given even worse jobs if they demur. When this gets old, have them "multi-tasking" at ever increasing speeds, which at first are funny, like Lucy Arnaz on the pie box assembly line; and then they will get less funny, with shocks being administered with mistakes...but on an intermittent basis.