In what order did you learn your class levels?
Who were your mentors?
What is your most self-damning quality?
What is your most self-redeeming quality?
What is your schtick/gimmick, as in for what are you THE expert (e.g. Master Locksmith, SuperSneak, Trapshooter, etc.)?
Who are your friends?
Who are your enemies?
Why were you arrested, as in, how did you get caught/captured/noticed/found?
Why were you convicted, as in, what was the damning evidence brought forward, a witness, the blood on your hands, what?
Why were you sent to the roughest toughest prison in the kingdom?
What are you looking forward to doing when you get out of prison?
And, how would you escape from prison?