I never really cared for most of the "20-50 Questions" lists myself. Too many of them are "questions" that are better handled through a simple stat listing, such as age, birthdate, hair color, and so on. That said, I once found a really interesting set of questions on some fansite (I think it was Blackjack's but I'm not sure anymore; it was so long ago) that I tweaked a bit. You can find it below.
- What’s your favourite colour? Any particular reason why?
- What do you want to wear at your next costume party?
- Under what circumstances, if any, would you sacrifice your life?
- What do you like or dislike about traveling?
- What makes life worthwhile for you?
- What’s the best thing you’ve ever done?
- Warfare or magical assault. Which do you fear more and why?
- What’s your favourite number?
- How do you believe the universe works?
- What sort of education have you acquired, and how? Did you enjoy the process?
- What great figure from mythology, history, or the media do you identify with, and why?
- What kinds of animal do you like to spend time with?
- What’s the worst thing you’ve ever done?
- Why are you running the shadows?
- Under what circumstances, if any, would you betray your friends?
- What’s your best party trick or show-off stunt?
- What manner of dying do you fear most?
- What do you expect to experience after you die?
- Is there an aspect of yourself you would like to change or part with? If so, what?
- How would you like to retire?
I just thought they asked more poignant questions that tell you more about who and what the character is as opposed to "What's your character's name?" and whatnot. More useful both as a player and a GM to see
into the mind of a character rather than surface traits that anyone could tell just by looking at him.