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Timmy Failure is a series of children's books by Stephen Pastis. It follows the story of Timmy Failure, a nine-year-old boy detective, who believes that he is the greatest mind of all time. Along with his business partner, the 1,500 pound polar bear Total, and his best friend, studious and intelligent Charles "Rollo" Tookus, Timmy leads his detective agency Total Failure, Inc. in solving crimes and defeating evil forces, such as Timmy's arch-nemesis, the "villainous" Corrina Corrina, and "criminal mastermind" Molly Moskins, who is largely infatuated with Timmy. However, Timmy is too clueless and egotistical to even realize the simplest clues to a mystery, resulting in near failures.

The series consists of seven books:

  • Timmy Failure: Mistakes Were Made
  • Timmy Failure: Now Look What You've Done
  • Timmy Failure: We Meet Again
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  • Timmy Failure: Sanitized For Your Protection
  • Timmy Failure: The Book You're Not Supposed to Have
  • Timmy Failure: The Cat Stole My Pants
  • Timmy Failure: It's the End When I Say It's the End

The main characters are:

  • The titular Timmy Failure, who believes he's the greatest mind of his time when in reality, he's a bit Book Dumb.
  • Fat genius Rollo Tookus, Timmy's "best friend".
  • Cloudcuckoolander Molly Moskins, who's in love with Timmy.
  • Corrina Corrina, AKA 'Weevil Bun,' 'Satan,' 'The Wedgie' and several other names. Timmy thinks she's evil. In the third book, it's revealed he has a crush on her. He doesn't act like he does.

Stephan Pastis revealed during his 2015 book tour that a feature film is to be in development by Disney, however, he's also warned that it'll be very toned down for audiences. It would later be revealed to be one of the first feature films set for Disney+ from director Tom McCarthy.

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The best usages of tropes in town, probably the state, perhaps the nation...

  • Adults Are Useless: Subverted. Timmy doesn't think much of the adult presence in his life, but his attempts to do things on his own always result in rather big problems, and his mom usually has to deal with the result in the end. Averted with Great-Aunt Colander, as she and Timmy develop a mutual respect. You can imagine how she felt when her boyfriend Crispin ended up endangering Timmy by forcing him to drive.
  • Adult Fear: While not focused on too much, Timmy's mom's struggles are revealed rather frankly as she struggles to hold a job while raising Timmy on her own.
    • When Timmy and Molly run away in the fourth book, their parents are appropriately terrified.
  • Alliterative Name: Molly Moskins.
    • Toody Tululu.
    • Emilio Empanada.
    • Corrina Corrina.
  • Arch-Enemy: Out of all of Timmy's supposed enemies, Scutaro is the one most openly antagonistic in return.
  • Art Shift: In-Universe - Timmy initially tried to get Total to illustrate his books, but "they were not good."
  • Badass Boast: Timmy makes them pretty much all of the time. Most common is "I am the founder, president, and CEO of the best detective agency in town, probably the state, perhaps the nation."
  • Big Bad: This is what Timmy thinks Corrina Corrina is.
  • Brilliant, but Lazy: Timmy. Subverted. We can all agree that Timmy's not exactly (verging at not at all) the best detective around, and it's 100% true that he's extremely lazy and inattentive when it comes to schoolwork (not to mention his terrible grades), but he is pretty clever and resourceful to pull off a few things to help lead him to "greatness".
  • Catchphrase: Timmy often says "Mendacity!" when he thinks someone is lying to him.
  • Cloud Cuckoo Lander: Molly Moskins.
  • Child Prodigy: Timmy thinks he's one of these. Rollo is more of one than he'll ever be.
  • Comically Missing the Point: Molly doesn't really seem to follow advice properly.
  • The Conscience: Rollo tries to be one, though isn't usually effective.
  • Cute Bruiser: While Toody Tululu may appear to be a sweet, innocent girl, she actually has quite a few anger issues, and is prone to threatening to beat someone up when she is mad about something.
  • The Cutie: Molly's naïve and sweet demeanor makes her this.
  • Didn't Think This Through: Timmy isn't prone to thinking or realizing he's made a mistake, but he gets this when he climbs up a model Eiffel Tower that's too tall to fall off of safely.
  • The Ditz: Molly is pretty airheaded, though it's been implied that she's smarter than she seems.
  • Every Man Has His Price: Timmy charges four dollars a day, plus expenses (chicken nuggets for Total), for his detective services, though it's unknown if he's ever actually been paid.
  • Face Palm: Timmy's mom makes one when she finds out he lied about losing her Segway.
  • Fat Best Friend: Rollo.
  • "Fawlty Towers" Plot: In the first book, when Timmy lies that his mom's Segway is missing because it's being used in a school play, resulting in him actually having to write and produce a play (however shoddily) from scratch.
  • First Kiss: In the third book, Timmy shares one with the most unexpected person of all people: Corrina Corrina!
  • For Want of a Nail: In "Now Look What You've Done", Timmy gets himself expelled and sent to a correctional school just so he has more time to work on a detective contest. When his mom finds out, she goes absolutely ballistic to the point of being broken.
  • Fragile Flower: Even though Molly is normally upbeat and excited, she's actually very sensitive. This is especially true in "Sanitized for Your Protection", when she and Timmy visit the Draconian hotel, and they ask the doorman if Yergi Plimkin lives there, but the doorman's constant questioning leads Molly to start crying uncontrollably until the doorman allows her and Timmy into the hotel.
  • The Hero: Timmy believes he's one of these. He's really not.
  • Genki Girl: Molly is almost always downright excitable.
  • Girly Bruiser: Toody might be a peaceful, Earth-loving and world-saving hippie, but she can get angry very easily.
  • Hyper-Awareness: Despite her often short attention span, Molly usually spots the obvious before anyone else clues in.
  • I Reject Your Reality: In every case he works on, Timmy ignores clues or even answers blatantly in front of him (such as seeing his client's little brother stuffing his face with candy while searching for the client's missing candy and only noting that the brother is messy), and always comes to the conclusion that Molly Moskins is the culprit. Depending on how much people are involved in these cases, they can get utterly flabbergasted by Timmy's worldview.
  • Ignorant of Their Own Ignorance: Timmy, no matter how many times people try to prove otherwise.
  • Imaginary Friend: It's heavily implied Total is one.
  • Insane Troll Logic: How Timmy pins all the cases on Molly Moskins, and how he works on cases in general, really.
  • Jerkass:
    • Timmy. He treats very few people with respect, even his best friends, though seems to have no idea about it as he is entirely preoccupied with his detective work. Most people are just confused by his antics, although they sometimes reach the point where he ends up hurting them.
    • Crispin Flavius in the first book, as he makes no secret of his disdain for Timmy's antics and his attempts to stop them ultimately result in him endangering Timmy.
    • Scutaro Holmes in the third book. The guy is a pretentious know-it-all involved in absolutely everything, and treats Timmy with condescension.
  • Kid Detective: Timmy himself, although he's not a very good one.
  • Kindhearted Simpleton: Molly might be ditzy and naive, but she's very caring towards others.
  • The Lancer: Rollo.
  • Large Ham: Timmy has a tendency to be this from time to time. Molly can be pretty hammy, too.
  • Never My Fault: Timmy has this attitude a lot, especially since a lot of the time he doesn't think what he's doing is wrong or mistaken.
  • No Indoor Voice: Molly is prone to shouting a lot, and so is her little brother, Micah.
  • No Sense of Personal Space: Molly never gives Timmy much personal space when she's around him.
  • Not-So-Imaginary Friend: While Total seems to be more and more likely on that route as the series progresses, some events in the first book seem rather weird with him being imaginary, particularly when Timmy creates the "Totalmobile" where Total pulls him on a wagon with a bucket of chicken nuggets in front of him. Also, one would wonder how Total being sent to the zoo and later returning played out if the bear is actually imaginary.
  • Not So Different: Timmy and Corrina Corrina, as she reveals in the third book: like Timmy, she hasn't had very many friends and even had a penguin for an imaginary friend. Though Timmy might have known that if he didn't establish Corrina Corrina as the Big Bad.
  • Oblivious to Love: Timmy does not comprehend Molly's extremely obvious declarations of love to him, sometimes viewing them instead as expressions of her villainy. However, given that he kissed Corrina Corrina in the third book, Timmy might be coming around to a few things.
  • Oddly Small Organization: Total Failure, Inc., despite Timmy's claims of greatness, is only operated by himself and Total. Timmy's desire to purchase the huge tower for his agency's office is out of a desire to look good, not to actually fit workers.
  • Perpetual Smiler: Molly is always happy-go-lucky and energetic, and you can see it in the books' illustrations, where she is almost always seen smiling.
  • Portmanteau: Molly is prone to combining words in her everyday speech, such as "handsomeful", "fantastical", and "splendiferous".
  • Put on a Bus: Molly Moskins in the third book, as she moves to Peru and is only mentioned a few times. The Bus Came Back big time in Book 4, however, as she moves back and has her most major role yet.
  • Repetitive Name: Corrina Corrina. One of her nicknames could be "The Girl So Nice They Named Her Twice".
    • Tom John John, Timmy's rival in the final book, has a middle and last name that are both the same.
  • Smarter Than You Look: Molly has shown a few times that she can be serious and competent when she needs to be.
  • School Play: Timmy claims to be using his mom's Segway in one after he loses it, which ultimately forces him to make one up from scratch. As such, he has to hold the play in Molly Moskins' backyard, which earned a lot of suspicion from his mom (he claims the ceiling tiles in the school auditorium fell down and that Molly was a prima donna).
  • Shout-Out: Molly is a huge fan of Hello Catty, an obvious parody of Hello Kitty.
  • Small Name, Big Ego: Timmy, however much he tries to claim that he is a big name.
  • The Stoic: Corrina Corrina appears to be this, most of the time.
  • Toilet Humor: Most apparent in the fourth book, which is called Sanitized for Your Protection and has Timmy standing in a toilet on the cover. The fact that the fans voted on the title and cover of the fourth book likely contributed to this.
  • Unfortunate Name: Timmy's family name. It was once Fayleure, but "somebody changed it". Timmy immediately claims that he is "anything but," although his actions throughout the series have made the name quite fitting.
    • While "Failure, Inc." was already a pretty bad name for a detective agency, it got worse once Timmy added Total's name to it to make it "Total Failure, Inc." When Total proved to be an ineffective business partner, Timmy was none too happy with the name change.
  • Unsympathetic Comedy Protagonist: Timmy. While he shares some sympathetic and heartbreaking moments with people (usually his mom), almost all the decisions he makes are poor and are always portrayed as such.
  • Vitriolic Best Buds: Timmy and Rollo definitely. Timmy and Total absolutely count too.
  • You Are Grounded: Timmy gets grounded in the first and second book. In the first book, he refers to it as being "imprisoned." A bit more severe in the second book, though, because Timmy was expelled from school and had to be homeschooled.
  • You Keep Using That Word: Timmy is firmly convinced that "garbanzo" is another word for the adjective "giant" despite multiple corrections from others saying that it actually refers to a type of bean.
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