This may not be new or funny for all of you more experienced players, but it made me laugh: My sim, who works on the criminal career, got arrested. When he went to jail, the officer told him something like: "You can reclaim your possessions when you leave. We don't want you to escape using your tragic clownfish!"
I would love to see my sim try to escape and threaten the guards with the tragic clownfish in his inventory.