Alter Ego was a video game released by Activision in 1986. The brainchild of psychologist Dr. John Favero it allowed players to play out an entire lifetime as if it were a Choose Your Own Adventure novel by playing out events based on hundreds of interviews conducted with people about their lives.
Now you can play a very faithful reproduction online.
Update: For $5 you can get a version for mobile phones using the Android operating system in the Android Market