Probably the most famous thief of all fiction, Raffles was a man-about-town and famous cricketer by day and a master burglar by night. When they were first issued at the turn of the century, these stories rivaled the popularity of Sherlock Holmes and established the prototype for The Saint, James Bond, and the other gentleman-rogue figures of popular fiction. Raffles has been called "the greatest cracksman in the literature of roguery" by the Encyclopedia of Mystery and Detection, while Ellery Queen has described Raffles as the "inspiration for the whole school of devil-may-care adventurers on the borderlines of the law, not least the eponymous James Bond."

E. W. Hornung was friendly with Sir Arthur Conan Doyle and married his sister. Hornung took his brother-in-law’s detective pair, Sherlock Holmes and Dr. Watson, and reincarnated them on the wrong side of the law as Raffles and Bunny, who pursued the business of getting a living by the entirely logical method of stealing it. Conan Doyle wrote in his autobiography: "I think I may claim that his famous character Raffles was a kind of inversion of Sherlock Holmes, Bunny playing Watson. He admits as much in his kindly dedication. I think there are few finder examples of short-story writing in our language than these, though I confess I think they are rather dangerous in their suggestion. I told him so before he put pen to paper, and the result has, I fear, borne me out. You must not make the criminal a hero."