It happens all too often. Your ‘heroes’ do something incredibly silly and end up in prison. Now you could just throw them in an empty cell but that would be boring. Roll on the table to see who they are sharing a cell with.
1) Quinn the Mad: This wizard was attempting to create a potion of mass polymorph when it exploded turning himself and a few other hapless victims into random animals. He is currently locked in a birdcage in the heroes cell. He will reward them with magic items if they aid his escape.
2) Kylar: This street urchin was caught stealing bread and was nearly beaten to death by the constable. He is presently dying when the heroes are thrown into the cell with him. The jailor doesn’t care about the state of the boy. If saved will look up to the heroes and will aid them with whatever they need.
3) Grandmother Helga: This lovely old grandmother is knitting a sweater for her granddaughter when the heroes are thrown into a cell with her. She is imprisoned for lighting her son-in-law on fire after breaking her granddaughter’s leg. She is going to be hung in the morning for murder and needs help relocating her daughter and granddaughter to a neighboring village where the rest of her family is, and also to deliver the sweater she’s finishing up.
4) Demon: There is a well dressed middle aged woman reclining on a beautiful mahogany chair when the heroes are thrown into their cell with her. The jailers don’t acknowledge her since they can’t see her. She explains that she can help the heroes escape the prison if they can help her with a little problem. She needs a priest killed who defaulted on a loan (a lie, he is an exorcist and she needs to get rid of him). If the heroes agree they are teleported out of the prison and are under the effects of a Geas spell to kill the priest.