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The Mysterious Benedict Society follows the adventures of Child Prodigy Reynard "Reynie" Muldoon, circus runaway Kate Weatherhall, Constance Contraire, and George "Sticky" Washington, a boy with a Photographic Memory. The books feature a mixture of high adventure, philosophy and intellectual challenges, as well as a number of science fiction elements.

The books were extremely well-reviewed as well as best-sellers. There were a total of three books in the series, making it a trilogy--The Mysterious Benedict Society, The Mysterious Benedict Society and the Perilous Journey and The Mysterious Benedict Society and the Prisoner's Dilemma. The final book resolved all remaining plot threads, ending the main series. A prequel titled The Extraordinary Education of Nicholas Benedict, featuring a childhood adventure of Nicholas Benedict, was published in 2012. A companion book, Mr. Benedict's Book of Perplexing Puzzles, Elusive Enigmas, and Curious Conundrums, was released in 2011. It features a number of puzzles based on the series and characters, as well as supplementary material such as character profiles, and a preview of Extraordinary Education.

This work contains examples of:

  • Abusive Parents: Sticky was financially abused by his parents, who, upon realizing his gift, would make him enter contests in order to get money.
  • Action Girl: Kate.
  • Agony of the Feet: This happens to S.Q. Pedalian in Perilous Journey when he drops a metal box on his foot after being insulted by McCracken, leader of the Ten Men.
  • Badass: Milligan. It must run in the family, as Kate is nearing this.
  • Brainwashed: The Whisperer
  • Child Prodigy
  • Circus Brat: Kate
  • Contemplating Your Hands: In the first book, the members of the society all study the backs of their hands after one of them points out the stupidity of the phrase "I know it like the back of my hand," since most people don't know the backs of their hands very well.
  • Conveniently an Orphan: Reynie fits this big time, since only kids who are "alone" pass the test.
  • Cool Teacher: Miss Perumal
  • Disappeared Dad: Kate's father left when she was two. It's later revealed to be Milligan, who was brainswept on a mission.
  • Eccentric Mentor: Mr. Benedict
  • Everyone Knows Morse: Averted. When Mr. Benedict says that the kids will have to learn morse code, Kate comments that nobody knows Morse. Mr. Benedict replies that that's exactly why it's so useful to them.
  • Evil Cripple: Mr. Curtain
  • Faux Affably Evil: The Ten Men have this down to a tee with their mask of polite mannerisms and cheerful chatter contrasting their thuggish, evil nature. "Now be a good little ducky."
  • Flashed Badge Hijack: This is inverted from the normal manner of things in The Prisoner's Dilemma in which Milligan actually hijacks a police car by flashing his superior credentials.
  • Fun with Acronyms: The Learning Institute for the Very Enlightened becomes L.I.V.E., which becomes, well... you know. In fact, Mr. Curtain seems to be quite fond of acronyms. Had his scheme in the first book succeeded, he would have gotten himself declared "Master and Secretary of All the Earth's Regions," or M.A.S.T.E.R. Additionally, he made up pamphlets describing a supposed "Sudden Amnesia Disease," with sufferers known as "S.A.D. cases." In actuality, S.A.D. was just a smokescreen to attract anyone who was hearing voices from his Whisperer to Nomansen Island, where he would then use the Whisperer to wipe their memories himself, so they wouldn't be a threat.
  • Gang of Bullies: The Extraordinary Education of Nicholas Benedict has The Spiders, a group of three bullies. Rather dimwitted, they've nevertheless managed to terrify the whole orphanage. Benedict almost always manages to outsmart them, escaping their torments, though they still cause him trouble by making him remain constantly on the alert and also terrifying anyone who would be friends with him.
  • Hey, You: Mr. Curtain refers to Number Two as "the woman" because he "refuses to refer to her by her ridiculous code name."
  • Hidden Purpose Test
  • Improbable Age: It's quite a shock to the group that Constance is only three in the first book.
    • Throughout most of the story, she's two.
  • Luke, I Am Your Father: Milligan is revealed to be Kate's father.
  • Living Lie Detector: Both Constance Contraire and Nicholas Benedict can usually tell when someone is lying about something.
  • Malaproper: S.Q. Pedalian, who tends to combine real words to form new ones, for example, "astounded" and "astonished" to make "astoundished," and also gets confused when it comes to figures of speech.
  • Not So Stoic: Milligan was pretty introverted and reserved until he remembered that Kate was his daughter.
  • Obfuscating Disability: Mr. Curtain uses a wheel chair and reflective sunglasses to cover up his narcolepsy.
  • Only Known by Their Nickname: Sticky and Number Two
    • Milligan could count, too, since even he doesn't know his real name. Curiously, even once he gets his memory back (as well as access to his old household and records), he still goes by "Milligan," and his real name is never even mentioned.
  • Orphanage of Fear: In The Extraordinary Education of Nicholas Benedict, the new orphanage that the titular protagonist is sent to isn't exactly awful in that nobody is starved, nor really abused, but it's certainly not a nice place to be either. Children that wake up screaming from a nightmare are forced to wear a dunce cap and most of the kids spend their days in fear of a Gang of Bullies called "The Spiders" whom the adults are too oblivious too do anything about. Nicholas seeks a way to escape his situation, until he realizes that as a genius, his efforts would be better spent finding a way to make conditions at the orphanage better for everyone.
  • The Password Is Always Swordfish: Early on in the first book, Mr. Curtain tells Reynie to "remember, control is always the key." Later, the group has to figure out the password for the keypad on Mr. Curtain's wheelchair and Mr. Curtain's maniacal ravings prompt Reynie to believe that it might be "control." As it turns out, it isn't, but Mr. Curtain's love of his home country of Holland leads him to believe that the password might be in Dutch. Since Sticky knows most languages, he asks him, and it turns out you just have to add an "e" to the end of "control." They do so, and it's correct.
  • Photographic Memory: Both George "Sticky" Washington and Mr. Benedict posssess an eidetic memory and are able to quickly scan through through books and then quote the contents from memory. Mr. Benedict is only shown demonstrating it in the prequel book The Extraordinary Education of Nicholas Benedict, but it does bring to mind a scene from the original book. Reynie is in Mr. Benedict's study, admiring all the books there, and asks Mr. Benedict if he's read all the books. Mr. Benedict replies "My dear boy, what do you think?"
  • Psychologist Teacher: Miss Perumal, Reynie's tutor.
  • The Radio Dies First: In the second book, The Mysterious Benedict Society and the Perilous Journey, Reynie Muldoon (the main protagonist) actually pitched the radio out of a train because he mistakenly did not consider the person on the other end to be trustworthy.
  • Red Baron: The various names of the Ten Men, including Sharpe, Garrote and the leader, McCracken. It's never specified for absolute certain that these aren't their real names, but it seems most likely that they're code names.
  • Rhymes on a Dime: Constance Contraire, when writing her poetry. In describing the poem that she wrote about donut holes, Mr. Benedict mentions recalling a "particularly felicitous rhyme between 'flaky bereft' and 'bakery theft'."
  • Room 101: The Waiting Room, which is so horrible that even those who have never been there cringe in fear of it. Sticky gets sent there, and it's just a room full of mud and insects; nevertheless, he is nearly broken by it. Later, Milligan gets captured and sent to it and it turns out to work to the party's advantage. He is able to hold his breath and sink down below the mud and then escape.
  • The Runaway: Three of the four main characters are runaways. Constance's situation is never explained in detail. Sticky ran away from overbearing parents, and Kate joined the circus after her father disappeared. In the end, Constance gets adopted, Sticky goes back to his very worried parents, and Kate's Disappeared Dad gets a Luke, I Am Your Father.
    • It's now been revealed that Constance was an orphan who ran away from the orphanage in order to avoid the Ten Men.
  • School for Scheming: The Learning Institute for the Very Enlightened.
  • Secret Test
  • Spy Speak
  • There Are No Rules: The Learning Institute for the Very Enlightened would like you to believe this.
  • Thou Shalt Not Kill: Milligan's refusal to kill an enemy, even if they deserve it because If You Kill Him You Will Be Just Like Him.

 Kate: Are you kidding? These guys are monsters! If that one fell into the water it would serve him right!

Milligan: You might think you mean that. But you'd feel differently if it were to happen and you were responsible. We're not like them, Kate. That's the entire point of trying to stop them.

  • Walk On Water: Referenced in The Mysterious Benedict Society and the Perilous Journey. When the kids follow Milligan despite his warning, Reynie uses the excuse that they figured the stairs were sound because they held his weight. Milligan replies that he walks lightly, so they should never let that be their guide. It is stated that Reynie isn't sure whether or not Milligan is teasing - "He wouldn't be entirely surprised to learn that Milligan could walk on water."
  • Younger Than They Look and Wise Beyond Their Years: Constance.
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