Bertie isn't as nice as he seems.In reality, he's a twisted version of The Pollyanna. His cheerful demeanor is due to some serious repression, resulting from a lifetime of mistreatment by his friends and relatives. The reason he goes along with whatever his aunts/the Drones/Jeeves say is that, if he examines his own desires too closely, his wall of repression will collapse and he'll end up going on a murderous rampage. In all likelihood, his apparent stupidity is also a front to protect him from the reality that everyone he knows is a Jerk Ass. This explains why someone as "mentally negligible" as Bertie is such a brilliant writer.
There is no Jeeves.He's just the Imaginary Friend of a sad, lonely man who lives alone— a kind of Anti-Tyler Durden, if you will.
The books are a tribute to all the author's dead friends.The books are in Christie Time- and full of feckless, foolish, harmless, silly, innocent men. Since the great war didn't happen, they happily avoided dying in charges on entrenched positions, choking on mustard gas, and suffering from PTSD. Instead, shenanigans and fancy clothes. Sort of an Alternate Ending for the Edwardian era.
Jeeves is robbing Bertie blind.What other reason would Jeeves benefit from serving Bertram Wooster? It's obvious he has aptitude for The Plan (pretty much every story is solved thanks to Jeeve's pulling one of this behind Bertie's and the reader's) and he has admitted that has accepted the fact he will have no other job after this one... one has to wonder who manages Bertie's finances...
Jeeves is a Time Lord.He is intellectually superior to everyone in the universe, has a prescient knowledge of how Bertie's plans are going to turn out, enjoys helping people, and seems to have all the answers. He also manages to convince everyone that he is in fact a woman in one episode, and moreover one attractive enough to be hit on multiple times, despite the fact that he does not look like one.
Jeeves is IagoAnd Bertie is Roderigo. Both are brilliant manipulators who are capable of controlling the slightest actions of every other character. Both play Batman Speed Chess with their social superiors and employers. And Jeeves has a history of manipulating Bertie for purely selfish reasons- the very first story he appears in has him breaking Bertie's engagement because the girl would have fired him. The only difference is the character's self images, which makes Jeeves after he worked out the inferiority complex.
Jeeves is an IgorA la Discworld. He disdained the family history for surgery, as well as the name, lisp, limp, and appearance, but has kept up being an extremely smart and efficient servant. He's always there when called for, never questions the Master, and is two steps ahead of the wildest scheme.
Honoria is a closet lesbianThe more likely a man is to say yes, the more terrifying she becomes. She is also known to be fond of active pastimes with female friends which would provide cover for other pursuits.
Reggie Pepper is Bertie's sonThey have the exact same personality, what?note And Reggie = Reginald = Reginald Jeeves! Obviously, Bertie named his son after his best friend. Why, then, is he Reginald Pepper and not Reginald Wooster? There are any number of possible reasons for this. Wooster could be a pen name. Alternatively, young Reggie could simply be using an alias to get away from his dad's embarrassing reputation. (As of The Inimitable Jeeves, rumors that Bertie is insane have been flying free and fast—who knows how much that line of thinking has skyrocketed since?)
Bertie has dependent personality disorder.Let's run through the symptoms. Extreme Doormat, unambitious, zero confidence in his own abilities, openly lets his valet run his life for him. (His reasoning being that, after all, Jeeves is better at it, right?) Afraid of what will happen if he ever loses Jeeves. Constantly seeks sympathy. Stays at the houses of people who can take care of him when Jeeves isn't around. In something of an Establishing Character Moment in "Extricating Young Gussie", he drifts around New York City looking for someone to help him, despite not knowing anybody there, and proceeds to "put [him]self unreservedly into the hands" of some random bartender. Yes, I got the link to the Wikipedia article from the Living Emotional Crutch page, but it seems to fit like a glove.
Bertie is an Unreliable Narrator.He's Obfuscating Stupidity; Jeeves, if he exists, is actually just an ordinary, unremarkable valet. Bertie is just reattributing a series of schemes that he thought up himself.note This can easily lead into the next WMG...
Bertie is secretly Batman.The very first. He uses his Rich Idiot with No Day Job persona to hide the fact that he goes out at night to catch criminals. Jeeves is the forerunner of Alfred.
Jeeves is a TV Genius.We're seeing him from Bertie's perspective, after all. In reality, he's smart, but not quite to the level he is in the books. (For instance, it may actually take him a little thinking before he whips out a scheme, and he doesn't always talk in that formal, casual manner.)
Bertie really is insane.Seriously, this isn't that much of a stretch; it's probably canon. What sane person would act like him? And note that this explains his writing. "Insane" does not equal "stupid". The only reason he hasn't been scooped up and tossed into "some sort of a home" is that Jeeves keeps his reputation up and takes care of him. In one story, Aunt Dahlia goes so far as to tell Bertie that the only reason he's not in a padded cell is that she has "influence with the lunacy commissioners."
In Thank You, Jeeves, Jeeves was planning to go back to Bertie all along.He initially gave his notice because he hoped it would make Bertie change his mind about moving to the country. When that didn't work, he signed up with Chuffy, having deduced that Bertie wanted to rent a house from him and knowing that this would guarantee his (Jeeves's) presence exactly where he'd be needed. He knew enough about Bertie's psychology to realize that the banjolele obsession wouldn't last, so he set everything up so that he could keep an eye on Bertie and rejoin his service as soon as the hated instrument was retired.
Brinkley was in league with Jeeves.Jeeves knew him from the valet agency and told him to act as insane and unreliable as possible so that Bertie would have second thoughts. Brinkley also did Jeeves the favor of burning down the house that contained the banjolele.
Jeeves is Merlin.White’s Merlin goes through time backwards, getting older and older the further back in time he goes (or, from everyone else’s perspective, gets younger and younger). There’s a scene, I think it’s from The Sword in the Stone, in which Merlin attempts to prove his credentials as a wizard by conjouring his hat from thin air. The only problem is he asks for ‘my hat’, not specifying ‘my magician’s hat’, and is promptly furnished with a top hat, which he mentions that he wore while celebrating the relief of the Siege of Mafeking, which occured in February of 1900, indicating that he was still an adult in the early twentieth century. Certainly old enough to be acting as a gentleman’s gentleman in the 1920’s. So, Bertie Wooster is either a descendant or reincarnation of Arthur Pendragon, and therefore the rightful King of the Britons. Merlin, in the form of Jeeves, is once again on hand to dispense aid, wisdom and gentle instruction (in the 20th century, however, one does not turn one’s employer into birds of the air and beasts of the field and so forth. That is simply Not Done in polite society). The last member of a Royal Family in the British Isles to be called Arthur was Arthur, Prince of Wales, eldest son and heir to the throne of Henry VII. He died before ascending to that throne, and was interred in Worcester Cathedral (and because British pronunciation had a huge falling out with British spelling somewhere back in the mists of time and are still not on speaking terms, it should be pointed out that ‘Worcester’ is pronounced ‘Wooster'). Frequently in the Jeeves canon, Jeeves himself is reported as seeming to appear and disappear, which Merlin was able to do in The Once and Future King. Jeeves undertakes what may be considered twentieth century equivalents to the typical pastimes of the classic image of the magician. He reads philosophers, in much the same way the wizards of yore will have done the works of the Ancient Greek, Roman and Arabic natural philosophers, and he’s frequently described as being supremely skillful in the concocting of both cocktails and potion-like hangover cures, and if that isn’t modern alchemy I should very much like to know what is. Jeeves’ encyclopedic knowledge of VIRTUALLY EVERYTHING IN EXISTENCE makes a lot of sense if you posit that he’s actually over two thousand years old and that his mental acuity is increasing as he grows younger. The surname ‘Jeeves’ is thought to be Matronymic (that is, deriving not from the father, but the mother). Merlin is said to have been the child of a human woman, and a demon, ghost or fairy, depending who you ask. Whatever manner of supernatural being fathered Merlin, it’s not exactly likely that they stuck around to do their share of night-feeds, meaning that Merlin was probably raised by his mum. Finally and crucially, Jeeves’ given name is ‘Reginald’. The name Reginald is a Latinisation of the Germanic name ‘Raginwald’ (occasionally ‘Raginald’), which is combination of the word Ragin, which means ‘advice’ or ‘counsel’ and Wald which means ‘rule’ or ‘ruler’. So the name Raginwald (and by extension its modern form ‘Reginald’) can be interpreted as ‘one who advises or counsels a ruler’.