 The stories were not all collected in one short story collection until they were featured, along with several early Jeeves stories, in the 1997 collection "Enter Jeeves".Two of the four Reggie Pepper stories published in "My Man, Jeeves" were later rewritten by Wodehouse as Jeeves stories, and one was rewritten as a Mr. Mulliner story.Reggie Pepper was inspired by the English "dude" roles that Wodehouse saw on the New York stage, and by the stock Edwardian aristocrat parts that Wodehouse had seen played by comedian George Grossmith Jr.

Reggie Pepper is a young gentleman who does not do any work, having inherited a great deal of wealth from his uncle Edward Pepper of Pepper, Wells, & Co., the colliery people.