47 pages • 1 hour read
Stephan PastisA modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.
Content Warning: This section of the guide includes discussion of bullying.
Timmy Failure is the protagonist and narrator of the story. He is characterized primarily by his ability to make infinite mistakes and to fail at everything he tries. Though Timmy fails, he doesn’t perceive his actions as failures because he sees the world in a way that nobody else does.
Timmy is illustrated as blank-eyed and small, and his only distinctive feature is the scarf he always wears. His sense of morality is questionable at best: He has no qualms about lying to his mother, insulting and using his best friend, or judging people like Corrina Corrina without getting to know them. Timmy sees himself as a highly skilled detective, if not the best in the world, and is completely oblivious to the fact that he misses every piece of evidence that he is given. He doesn’t see his own mind as an obstacle to success; instead, he blames his mother, his school, his best friend Rollo, Corrina Corrina, Molly, and even Total. This characteristic shows how much maturation Timmy has to do, setting up his character arc, in which he will grow more aware of the effect of his actions on others.
Timmy also engages in fantastical thinking more than he thinks in realistic terms. He believes he will soon be able to afford an office that costs $54,000 to rent, pay all his mother’s bills, and successfully destroy Corrina Corrina’s business. Timmy also sees Total as real and blames him for hindering his business by eating garbage or sleeping too much. Timmy’s confidence is never-ending and often gets him into trouble because he doesn’t know when to quit: “I am not most. I am Timmy Failure. And no person or government or force of nature can stop me” (103). This hyperbolic speech is also characteristic of Timmy. His intelligence is high in some regards, as he uses complex vocabulary and has a great deal of worldly knowledge, but at the same time, Timmy makes rookie mistakes like thinking “TP” stands for “tiny people” (67) or ignoring Gunnar’s brother covered in chocolate.
When Timmy’s world begins to change, he finds it all overwhelming and doesn’t want to discuss it much, choosing instead to live in his imaginary world. He and his mother have to move into a smaller apartment, and his mother begins dating a man who is ill-mannered and temperamental. At the same time, Timmy is pressured to start focusing on school, which is something he struggles to do because he is easily distracted. Instead of addressing these real-world issues, Timmy puts most of his focus into his agency, sabotaging Corrina Corrina, and finding the Segway, which eventually becomes all one related goal. As things tumble out of control over the course of the novel, The Destructive Power of Lies is highlighted through the conflict it causes in his life. Through the events of the story, Timmy learns that he can mature without letting go of who he is, demonstrating the theme of Being Oneself While Being Open to Improving.
Timmy’s relationship with his mom is an important feature of his character and the story. Although Timmy is often oblivious of the effect of his actions on others, he is also keenly aware of his mother’s state of mind, marking it by the number of times she drives the Segway or how often he finds her at the table, surrounded by bills. With their relationship, the story explores The Unbreakable Bond Between Mother and Son. Even though Timmy’s mom loses her patience at his lies and antics, she also recognizes the wonder of his imaginary world and allows him to be himself.
Timmy’s mom is an important figure in his life and the center of much of Timmy’s stress. The drawings of her illustrate this tension: Her face is not shown until the end of the story, and until then, the illustrations only show silhouettes or portions of her, like her hands or her hair. She is a loving and supportive mother, but she is often tired and anxious about the difference between her paychecks and her bills. Timmy tells his mother that he will one day be able to afford to pay her bills, and the affection she responds with, kissing and tickling him, shows that even though she is anxious, she still appreciates Timmy’s unique perspective. She also reads to Timmy every night, usually stories that Timmy wrote and illustrated himself, showing her support for his creativity and imagination.
Timmy’s mom works at a stationery store and doesn’t get as many hours as she used to, and her one escape is to ride her Segway around the block. Overall, she is patient with Timmy’s antics; however, her patience runs out on the day of the play, which happens to coincide with the news that Timmy will have to repeat a grade. While Timmy’s mother was always supportive of his agency and his imagination, she becomes stricter just long enough to help steer Timmy back in the right direction. After a period without Total and focusing on school, Timmy’s grades start to improve, and he and his mother are able to compromise about his pretend games. The unbreakable bond between mother and son is demonstrated through Timmy’s mother’s unconditional acceptance of who her son is and her ability to forgive his many mistakes.
Total is Timmy’s imaginary polar bear, though the fact that he is imaginary is not made fully evident until later in the story. Total is said to have wandered south from the Arctic in search of food and found himself in Timmy’s kitchen. Timmy adopted him, and now they are both close friends and business partners. Timmy loves having Total on board but also considers him an obstacle to success who is “lucky to be employed” (65), since Total tends to eat garbage and destroy things rather than do any sort of detective work. Total sits outside the fence and watches Timmy play at recess, and his favorite foods are chicken nuggets and Rice Krispies squares.
Total is a manifestation of Timmy’s imagination and features prominently in both the text and illustrations of the book. Timmy considers Total to be his closest ally, and they are always “two against the world” (189). When Crispin Flavius points out that Timmy’s games are “pretend,” including Total, Timmy can’t handle hearing this and bolts from the car. The thought of letting him go is extremely difficult and feels wrong to Timmy. Total is a symbol of Timmy’s childhood imagination and reluctance to grow up. When Timmy’s mistakes start to pile up, Timmy’s mom draws the line, and he has to say goodbye to Total for a while. However, soon, Timmy learns to create a balance by Being Oneself While Being Open to Improving, and Total is welcomed back into his life—part of finding that balance is allowing the space for his imagination, and his imaginary friend, to exist alongside the real world.
Rollo Tookus is Timmy’s best friend, though Timmy doesn’t treat his best friend very well. Rollo’s actual first name is Charles, but he has acquired this nickname due to his weight, which Timmy never hesitates to point out. Timmy also calls Rollo an “idiot” because Rollo is most interested in studying and getting grades high enough to one day go to Stanford. Timmy finds this all a massive waste of time and doesn’t see the point in studying or caring about his education. Timmy also employs Rollo for all sorts of undesirable tasks, often threatening to ruin Rollo’s grades if he doesn’t comply. He has Rollo dress up like a sunflower to stake out the bank, and Rollo ends up locked in a safe overnight. Timmy also despises the fact that Rollo’s tutor is his own worst enemy, Corrina Corrina. He considers this a betrayal of their friendship and tells Rollo this often.
In truth, Rollo is often the one who makes the correct deduction in Timmy’s mysteries. He is a steadfast, loyal friend despite Timmy’s condescending and sometimes hurtful treatment. His constancy allows Timmy the space to grow and change, playing a large part in Timmy’s character arc. After Timmy has made many mistakes and ruined Rollo’s GPA, he finally starts to see the flaws in his ways and apologizes to Rollo. Rollo is ever-forgiving and always willing to give Timmy another chance. He does occasionally try to help Timmy and point out his mistakes, like when he explains that Molly has a crush on Timmy, but Timmy never listens to Rollo’s keen advice.
Corrina Corrina is Timmy’s nemesis, although this dynamic is one-sided because Corrina Corrina hardly knows who Timmy is. Timmy introduces Corrina Corrina with an illustration of a black square over her face that emphasizes how much he dislikes her and wishes she would vanish. Corrina Corrina is in Timmy’s group at school, and he sees her as smarter than he is. It is clear that Timmy is jealous of Corrina Corrina and intimidated by her, and he compensates for this by regularly trying to convince his reader that he is, in fact, the better detective: “I am inferior to no one” (154). Corrina Corrina outwits Timmy professionally at many points; she has a fancy detective office in a bank that her father owns, complete with large columns out front, like the ones that Timmy desires. She also intercepts Timmy’s client at one point, though she apparently does so without realizing it.
Corrina Corrina acts as a foil for Timmy in the narrative. She and Timmy have a lot in common; they both like detective work and polar bears. Additionally, both Corrina Corrina and Timmy have single parents. Corrina Corrina lives with her father and often misses him when he works too much. However, she serves as one of the people whom Timmy blames for his own actions and repercussions, and he remains convinced that Corrina Corrina is an enemy and an antagonist. Ironically, when Timmy gets a chance to read through Corrina Corrina’s diary at one point, he finds an entry that reads, “The weird kid in our group makes us all fail the test” (175). It heavily implies that Corrina Corrina doesn’t even know Timmy’s name, let alone have plans to sabotage his business or steal his Segway.
Molly Moskins is Timmy’s classmate and the girl who happens to have a serious crush on him. Timmy finds Molly odd because she smells like tangerines, has mismatched pupils, and behaves in unusual ways. For example, she shows up at Timmy’s apartment in the middle of the night and breaks his window with a dirt clod. She grabs Timmy during the play and refuses to let go. She also makes up stories about her shoes getting stolen repeatedly, which leads Timmy to assume she must be some sort of “international shoe thief” (119). Molly serves as another example of how badly Timmy can misinterpret things; he doesn’t understand that her actions, while sometimes inappropriate, are fueled by her crush. Instead, he comes to believe that she is a master criminal, responsible for many of the crimes he is trying to solve. With Timmy’s relationship with Molly, Stephan Pastis highlights the narrowness of Timmy’s perspective again.
Crispin Flavius is Timmy’s mother’s boyfriend for a portion of the story. When Timmy meets Crispin, he immediately senses that something is off but doesn’t know how to articulate this and instead points to superficial aspects of Crispin like his upturned collar, his soul patch, and his (to Timmy) suspicious love of raisins. In Timmy’s illustrations, Crispin has a distinctive thick, single eyebrow and is always scowling. He takes every opportunity to lecture Timmy and try and convince him that he should change. While Crispin does have some points about Timmy’s total lack of responsibility and self-centeredness, he condescends to Timmy, calling him a “weirdo” and telling him to grow up. Crispin fails to understand, as Timmy’s mom does, that Timmy’s imagination, though sometimes out of control, is also something to be enjoyed and celebrated. Through his character, Pastis highlights how not to convince Timmy to change, contrasting with Timmy’s mom’s more evenhanded approach and highlighting her strengths as a parent.