Reginald "Reggie" Pepper is a fictional character who appears in seven short stories by English author P. G. Wodehouse. Reggie is a young man-about-town who gets drawn into trouble by trying to help his pals. He is considered to be an early prototype for Bertie Wooster, who, along with his valet Jeeves, is one of Wodehouse's most famous creations.

The Reggie Pepper stories were originally published in magazines. Four were included in My Man Jeeves (1919), and the other stories appeared in later miscellaneous collections. 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.

Inspiration 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.Wodehouse (2013), A Life in Letters, p. 72, stated by editor Sophie Ratcliffe.

Life and character 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. He went to Oxford with Freddie Meadowes and Bill Shoolbred. In "Rallying Round Old George", he has a valet named Harold Voules, though he fires Voules by the end of the story. Later, in "Concealed Art", he employs a valet named Wilberforce.Garrison (1991), pp. 141–142. Reggie sometimes meets his friends at his club, which is unnamed. (The stories in which he appears were written before Wodehouse had invented the Drones Club). Reggie is not ambitious and is content simply to watch traffic from the window of his club, though he is also curious about the affairs of his friends, as he states in "Concealed Art". Not interested in working himself, he respects others who work.

In the stories, Reggie tries to help his friends with their problems. Despite being considered not very intelligent by his friends, he occasionally experiences a flash of inspiration, which he sometimes refers to as getting a "brain-wave".Reggie gets what he calls a "brain-wave" (or "brain wave", or "brainwave") in "Helping Freddie", "Disentangling Old Percy", "Rallying Round Old George", "Concealed Art", and "The Test Case". His friend Bobbie Cardew gets a brain-wave in "Absent Treatment". The only story that does not mention brain-waves is "Doing Clarence a Bit of Good". However, his well-intentioned interference generally backfires somehow. Reggie himself notes this, stating "Doesn't some poet or philosopher fellow say that it’s when our intentions are best that we always make the most poisonous bloomers? I can’t put my hand on the passage, but you’ll find it in Shakespeare or somewhere, I’m pretty certain. Anyhow, it’s always that way with me." Reggie also says something similar at the end of "The Test Case".

Continually unlucky in love, Reggie states in "Rallying Round Old George" that he has been turned down dozens of times. He was once in love with Elizabeth Shoolbred and was engaged to her for about a week, but she married the artist Clarence Yeardsley instead. He also came close to marrying Ann Selby in "The Test Case". Reggie is not engaged or married at the end of the stories, though he does not seem troubled by this. He is ultimately thankful that he did not marry Elizabeth Yeardsley, who proves to be rather manipulative, or Ann Selby, since she is a strong-minded girl who would have tried to change him.

The American editions of the Reggie Pepper stories differ slightly from the British editions. In the American editions, Reggie Pepper appears to be American and lives in New York instead of London. Another difference is that the money he inherits from his uncle came from a safety razor company rather than a coal company.

Prototype for Bertie Wooster Reggie Pepper served as a prototype for Wodehouse's later character Bertie Wooster.Wodehouse (2013), A Life in Letters, p. 74. According to editor Sophie Ratcliffe, Reggie Pepper was "the prototype for Bertie Wooster". In a letter to a fan also named Wooster who asked Wodehouse about the origin of Bertie Wooster's name, Wodehouse wrote, "I can't remember how I got the name Wooster. I think it may have been from a serial in the old Captain, where one of the characters was called Worcester. The odd thing is that the Bertie W. character started out as Reggie Pepper, and I don't know why I changed the name."

Notably, it is Bertie's valet Jeeves who would eventually be named "Reggie" like Reggie Pepper, and Bertie Wooster received the middle name "Wilberforce", which is the name of Reggie Pepper's valet.Jeeves's first name was revealed in Much Obliged, Jeeves (1971); Bertie's middle name was revealed in The Mating Season (1949) and also mentioned in Much Obliged, Jeeves.

The Reggie Pepper stories

Reggie Pepper appears in the following stories:

"Absent Treatment" UK: Strand Magazine, March 1911 US: Collier's Weekly, 26 August 1911

Plot Reggie Pepper's friend Bobbie Cardew, who was very forgetful at the time when the story takes place, invites Reggie to his home for dinner. Reggie sees that Bobbie's wife Mary is very well dressed. Her manner is strained. The following day, Bobbie sullenly tells Reggie that the previous day was his and Mary's first wedding anniversary. Bobbie's forgetfulness continues to create problems between him and Mary, though he does remember to give Reggie money he owes him, feeling it is important to pay a debt. Reggie says Bobbie should try to remember dates for his wife, but Bobbie does not think dates really matter.

For months, Bobbie continues to forget things despite warnings from Reggie. One day in their club, a distressed Bobbie tells Reggie that Mary has left him. She wrote him a letter saying that she will only return when Bobbie cares enough to remember her birthday, which Bobbie has forgotten. After Reggie and Bobbie discuss other ideas for determining her birthday, Bobbie suggests they search through astrology books that describe the character of people born in certain months to find a description that matches Mary. This plan is unsuccessful, as each character description is applicable to Mary.

Bobbie thinks hard about the problem for weeks, and Reggie observes that Bobbie is becoming more mindful as a result of his efforts. Eventually, Bobbie remembers the show he and Mary saw on her last birthday at the Coliseum, narrowing the search down to six days in May. In the middle of the night, Bobbie calls Reggie, waking him up, and says they saw a matinée, which means the show was on Wednesday or Saturday. Reggie reminds him that there are daily matinées at the Coliseum, which disappoints Bobbie.

Reggie remembers that he had lunch with Bobbie that day, which Bobbie paid for. Bobbie looks in his cheque-book and happily discovers their lunch was on the eighth. Reggie then calls a hotel, and asks to speak to Mrs. Cardew. He tells her that Bobbie has remembered her birthday. Initially excited, she asks if Bobbie has been worried. Proud of their scheme, Reggie replies that Bobbie has been very worried, and is surprised when Mary berates him for letting Bobbie become so concerned. In the end, Reggie notes that he is still Bobbie's friend but is scorned by Mary, despite having acted with the best intentions.

The British edition of the story takes place in London while the American edition takes place in New York. In both versions, Reggie's wealth was inherited from his uncle, though in the British edition, the money came from the coal industry, whereas in the American version, it came from the safety razor industry. The American version is slightly longer.

"Helping Freddie" UK: Strand Magazine, September 1911 US: Pictorial Review, March 1912 (as "Lines and Business")

The story was later rewritten as a Jeeves story. (See "Fixing it for Freddie".)

"Disentangling Old Percy"

UK: Strand Magazine, August 1912 US: Collier's Weekly, 30 March 1912 (as "Disentangling Old Duggie")

Plot

The well-meaning young gentleman Reggie Pepper advises his friend Percy Craye to consult a palmist named Dorothea. Though initially reluctant, Percy is ultimately happy after meeting Dorothea, who is really a widow named Mrs. Dorothy Darrell. Percy makes money after being encouraged by her optimistic reading and thinks she is wonderful. Three weeks later, Florence Craye, Percy's older sister, tells Reggie that Percy is engaged to the palmist. Florence is class-conscious and strongly disapproves of the match.

Hoping to help Percy, Reggie suggests that if Florence acts as if she approves the match and invites Percy and Dorothea to the family's country house, Percy will realize that he does not belong with Dorothy and will end the engagement. Florence likes the idea and tells Reggie to come to the house with Percy and Dorothy. Reggie informs Percy about the plan; Percy is confident that his love for Dorothy will prevail.

At the Crayes' country house, Percy really does change his mind about the engagement under Florence's influence, and Dorothy leaves for London. Back in London, Reggie sees Percy's older brother Edwin, Lord Weeting, who is unusually happy. Florence is upset after learning that Edwin has been spending time with Dorothy, and orders Reggie to talk to Dorothy. Reggie learns from Dorothy that she is becoming close to Edwin to get revenge on Florence, though she is also genuinely helping Edwin learn to enjoy life after being oppressed by Florence. Dorothy does not deny that she is engaged to Edwin. Florence commands Reggie to tell her widowed father, Mr. Craye, Lord Worplesdon, that Edwin is engaged to a palm reader.

Reggie goes to Worplesdon's club and tells him that Edwin is engaged to a palmist, but Worplesdon does not seem to disapprove. Edwin arrives, and Worplesdon sees that Edwin is happier than before. Worplesdon and Edwin have fun in London. To avoid Florence, Reggie goes to Nice in France. He is surprised to find Edwin there, enjoying himself. He also sees Dorothy, who became friends with Lord Worplesdon after helping Edwin enjoy life. Dorothy says that she hopes someday to win Florence over because she wants all her children to love her. This confuses Reggie. Dorothy explains that she considers Lord Worplesdon's children her own since she married Lord Worplesdon.

The British version of the story, "Disentangling Old Percy", takes place in London, while the American version of the story, "Disentangling Old Duggie", is set in New York. Reggie Pepper's friend is named Percy Craye in the English version and Douglas or "Duggie" Craye in the American version. In the British version, the elder Craye has the title "Lord Worplesdon" and Edwin is "Lord Weeting", while in the American version, the family lives near Philadelphia and is not part of the British peerage.

"Rallying Round Old George" UK: Strand Magazine, December 1912 US: Collier's Weekly, 27 September 1913 (as "Brother Alfred")

The story was later rewritten as a Mr. Mulliner story. (See "George and Alfred".)

"Doing Clarence A Bit of Good" UK: Strand Magazine, May 1913 US: Pictorial Review, April 1914 (as "Rallying Round Clarence")

The story was later rewritten as a Jeeves story. (See "Jeeves Makes an Omelette".)

"Concealed Art"

UK: Strand Magazine, February 1915 US: Pictorial Review, July 1915

Plot