Princess Maker

The player is in charge of and must raise a war orphan, Maria, after defeating an evil demon. There are 74 possible endings, ranging from humble jobs such as a soldier or a mason, to prestigious jobs such as Archbishop or Prime Minister, to "dark side" jobs such as prostitute or crime lord. In addition, numerous factors decide whether or not the daughter is successful at her job, whom she marries, and whether she has children of her own. (wikipedia.org)