Timmy Failure
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50 free Timmy Failure trivia questions with answers — literature quiz, new questions added Oct 2026.
Timmy Failure is the self-proclaimed greatest detective in town, and almost certainly the worst. Stephan Pastis's illustrated series follows him, his enormous and very lazy partner Total, and a cast of classmates he mostly misunderstands. Its deadpan humor has made it a favorite for reading quizzes and book reports. This quiz covers the whole series, with plenty on Mistakes Were Made and Sanitized for Your Protection: the cases, the clues Timmy misses, the friends and rivals, the family upheavals running underneath the jokes, plus the author and the film adaptation. It suits readers checking what they remember after finishing a book, parents and educators who want quick comprehension questions, and fans who simply want to test themselves.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Total, the lazy business partner of boy detective Timmy Failure, is what kind of 1,500-pound animal?
A polar bear
A polar bear called Total supplies half the name of the agency, Total Failure Inc. Readers still argue over whether he is real or a figment of Timmy's imagination.
Q 02The Failuremobile that Timmy Failure borrows from his mother in Mistakes Were Made is really what vehicle?
A Segway
A Segway belonging to his mom is the grandly named Failuremobile. Losing it becomes the biggest mystery of the first book.
Q 03Timmy Failure author Stephan Pastis is best known for which long-running newspaper comic strip?
Pearls Before Swine
Pearls Before Swine made Stephan Pastis famous long before Timmy arrived. He says the tight space of a daily strip taught him the value of every word.
Q 04The Timmy Failure books mix a boy's narration with cartoons, a format modeled on which popular children's series?
Diary of a Wimpy Kid
Diary of a Wimpy Kid set the template. One reviewer noted that, like its hero Greg, Timmy isn't always likable: he is rude to friends and mean to imagined enemies.
Q 05Which classmate does Timmy Failure treat as his nemesis and refuse even to name in Mistakes Were Made?
Corrina Corrina
Corrina Corrina is the girl Timmy calls his nemesis. In the film version she is friendly to him and seems unaware that any feud exists.
Q 06Which best friend of Timmy Failure is so obsessed with getting into "Stanfurd" that he botches a spy mission?
Rollo Tookus
Rollo Tookus is the grade-obsessed friend Timmy keeps dragging into cases. In the prequel he acts as Timmy's biographer and adds exasperated footnotes.
Q 07In Timmy Failure: Sanitized for Your Protection, a road trip ends in which city, where Doorman Dave is moving?
Chicago
Chicago is where Doorman Dave, the boyfriend of Timmy's mother, is relocating. Timmy resents the journey because it interrupts a case he wants to crack.
Q 08The film Timmy Failure: Mistakes Were Made, directed by Tom McCarthy, was released on which streaming service?
Disney+
Disney+ released the film in February 2020, a few months after the service launched. It was pulled in 2023 and later reissued on video-on-demand platforms.
Q 09Before creating Timmy Failure, cartoonist Stephan Pastis spent nearly a decade in the Bay Area working as what?
A lawyer
A lawyer by training, Pastis defended insurance cases from 1993 to 2002 and disliked the work. He sketched his first comic character during a dull class at law school.
Q 10The film Timmy Failure: Mistakes Were Made is set in which American city, where it was also filmed?
Portland
Portland is both the setting and the main filming location, with cameras rolling there in the summer of 2018. Its bearded hipsters are the Russians Timmy believes he is outwitting.
Q 11In Mistakes Were Made, Gunnar's brother gives Timmy Failure which alibi when some sweets go missing?
He was eating candy
He was eating candy, the brother says, and Timmy is stumped despite the wrappers strewn all around. It is early proof that he is a terrible sleuth.
Q 12A classmate with a crush pelts Timmy Failure's bedroom window with which chocolates in Mistakes Were Made?
Hershey's Kisses
Hershey's Kisses hit the glass as the lovestruck girl tries to win his attention. She also tells Timmy she adores him and, in one chapter, hugs him.
Q 13During a group test in Mistakes Were Made, how does Timmy Failure misuse the Scantron answer bubbles?
Q 21The school detective contest in Timmy Failure: Now Look What You've Done asks who stole which object?
A globe
A globe belonging to the principal is the staged theft, complete with suspects and clues. Timmy is sure the $500 prize will set him up for life.
Q 22Which injury does Timmy Failure suffer twice in quick succession in Now Look What You've Done?
A broken leg
A broken leg strikes twice: he breaks the left one almost as soon as the cast comes off the right. The slapstick also costs a window and some topiary.
Q 23In Timmy Failure: We Meet Again, which legendary nature project that earned an A+++++ does Timmy hunt for?
The Miracle Report
Drawing dot-to-dot pictures
Drawing dot-to-dot pictures with the bubbles drags down the whole group's score. Timmy also sketches his agency's future offices on the classroom world map.
Q 14Which name does Timmy Failure write on his test papers in Mistakes Were Made, reasoning it is the world's most common?
Chang
Chang goes on all his papers because Timmy figures the odds are with him. Logic like that is why he risks being held back a grade.
Q 15In Mistakes Were Made, Timmy Failure is baffled to catch Flo, the fearsome-looking librarian, reading which poet?
Emily Dickinson
Emily Dickinson is the surprise, since Timmy insists Flo reads only about crushing things with his fists. One reviewer likened Flo to a Hells Angel.
Q 16Señor Burrito, a cat in Timmy Failure: Mistakes Were Made, dunks a paw into what whenever Timmy looks away?
His tea
His tea is the target: Señor Burrito sits with one paw sunk past the elbow in the teacup. A reviewer longed to tear out the illustration and frame it.
Q 17Which make of car plows through a wall into a teacher's living room in Timmy Failure: Mistakes Were Made?
A Cadillac
A Cadillac careers out of control and ends up in the living room, yet Timmy walks away without a scratch. The man dating his mom drives one.
Q 18What nickname does Timmy Failure give Mr. Jenkins, the teacher who appeals to his imagination in Mistakes Were Made?
New Guy
New Guy is Timmy's name for Mr. Jenkins, who turns learning into something the boy can relate to. In the film the character becomes a school counselor instead.
Q 19In Mistakes Were Made, Timmy Failure's business-speak narration says he does what with his mother instead of talking?
Teleconferences
Teleconferences is his word for an ordinary chat with Mom. Timmy also believes his agency is on the verge of joining the Fortune 500.
Q 20In Now Look What You've Done, Timmy Failure and his mother move into a mansion belonging to which relative?
His great-aunt
His great-aunt Colander takes them in while his mom is out of work. Eccentric and ambitious, she becomes Timmy's unlikely new ally.
The Miracle Report is the fabled assignment Timmy believes will rescue his grade. Rumors of plagiarism soon sweep the school.
Q 24In Timmy Failure: We Meet Again, Timmy's mother makes him play which sport and then dates his coach?
Baseball
Baseball is forced on Timmy, and his mom ends up dating the coach. She sees two men in this book, and both play large roles in his life.
Q 25Which gadget belonging to his mother does Timmy Failure often ride around on in We Meet Again?
A Roomba
A Roomba, his mom's robot vacuum, carries him through the third book. He barrels through life on it with little thought for others, yet classmates keep trying to connect with him.
Q 26Timmy Failure begins We Meet Again under which school penalty, with a principal waiting for him to slip up?
Academic probation
Academic probation hangs over Timmy all book, so a bad mark on his nature assignment could sink him. Worse, he must do it with his archrival.
Q 27The road trip in Timmy Failure: Sanitized for Your Protection eats up which school holiday Timmy wanted for sleuthing?
Spring break
Spring break vanishes because his mother makes him help her boyfriend, Doorman Dave, move house. Molly Moskins and her family come along for the ride.
Q 28What has been stolen in the case Timmy Failure tries to solve on the road in Sanitized for Your Protection?
Charity money
Charity money raised by a group called YIP YAP has vanished. It was meant to buy books for a bookless boy named Yergi Plimkin.
Q 29Before handing back what she stole in Sanitized for Your Protection, Molly Moskins forces Timmy Failure to do what?
Dance with her
Dance with her is the price Molly sets, and Timmy is not impressed. She had been his prime suspect in the case.
Q 30In Sanitized for Your Protection, Timmy Failure's sidekick Total leaves a trail of wrappers from which sweet treat?
Bonbons
Bonbons are Total's weakness, and their papers mark his path of destruction along the route. One review wondered whether he would spend all the agency's hard-earned money on chocolate.