Detective fiction highlights those qualities of masculinity that are most valuable to a contemporary culture. In mysteries a cultural context is more thoroughly revealed than in any other genre of literature. Through the crimes, an audience can understand not only the fears of a particular society but also the level of calumny that society assigns to a crime. As each generation has needed a particular set of qualities in its defense, so the detective has provided them. Through the detective's response to particular crimes, the reader can learn the delineation of forgivable and unforgivable acts. These detectives illustrate positive masculinity, proving that fiction has more uses than mere entertainment. In this paper, I trace four detectives, each from a different era. Sherlock Holmes lives to solve problems. His primary function is to solve a riddle. Lord Peter Wimsey takes on the moral question of why anyone should detect at all. His stories involve the difficulty of justifying putting oneself in the morally superior position of judge. The Mike Hammer stories treat the difficulty of dealing with criminals who use the law to protect themselves. They have perverted the protections of society, and Hammer must find a way to bring them to justice outside of the law. The Kate Martinelli stories focus more on the victims of crime than on the criminals. Martinelli discovers the motivations that draw a criminal toward a specific victim and explains what it is about certain victims that makes villains want to harm them. All of these detectives display the traditional traits of the Western male. They are hunters; they protect society as a whole. Yet each detective fulfills a certain cultural role that speaks to the specific problems of his or her era, proving that masculinity is a more fluid role than many have previously credited.