Here's mine, Ronnie Barker as Norman Stanley Fletcher and Richard (KAte's dad) Beckinsale as Dober, from Porridge.
Still can't find good screencaps for my original idea. But I may need to step up my game here, so...does this count? If not, I'll stick with the Joker. And anyone who enters the jail without bars from Support Your Local Sheriff will get my vote.
^ I wanted to use the jail cell from Support Your Local Sheriff, but couldn't find any good screencaps.
My only quibble would be that it's not actually a prisoner or a prison but someone telling you to go there. It's a fine point, I admit, but otherwise isn't every apprehension in media then a "prison" or "prisoner" picture? Which is my way of suggesting I'd stick with the Joker if I were you.