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Max Keeble
Portrayed by Alex D. Linz: The main character - a cunning 12-year-old boy who decides to get revenge on all of his school tormentors before his family is forced to move.
- Ambiguously Jewish: With his funny name, obsessive-compulsive mother, and dad's quirky sense of humor and background in show business (okay, advertising), he probably qualifies as this.
- Butt-Monkey: Max contends with two bullies, the principal and two teachers as well as an evil ice cream man.
- Chekhov's Skill: His newspaper throwing.
- Highschool Hustler: He pulls this off but is actually good kid. He only embraces this when he puts together that his moving will save him from the consequences.
Robe (Robert)
Portrayed by Josh Peck: Max's male best friend - an obese slob who has poor hygeine, but is quite intelligent.
- Big Fun: He can lead all of his fellow students and the band members in a movement against the bullies.
- Fat Slob: A more loveable version.
- Only Known by Their Nickname: You can count the amount of times he is called "Robert" throughout the film with one hand and fingers to spare.
- Vomit Discretion Shot: After Troy traps him in a see trough glass tank, triggering his claustrophobia.
Megan
Max's female best friend - a sweet, enthusiastic girl who loves band and other extracurriculars.
- Unlucky Childhood Friend: With Max. At least at first.
Elliot T. Jindrake
The evil, tyrannical principal of Curtis Junior High School. His goal is to reallocate the near entirely of school's budget to build a football stadium over an animal shelter, all in hopes of impressing the superintendent enough to take his job. He has a complete disregard for the wellbeing of anyone else besides himself.Portrayed by Larry Miller
- Big Word Shout: One of the few competent things he can do as principal is silence a room, no matter how big and noisy, by yelling "CEASE!"
- Chewing the Scenery: Miller definitely makes the most of his scenes.
- Dean Bitterman: He really, really hates the children of his school and the animal shelter sub-plot is as much driven by being a jerk as it is trying to be a Professional Butt-Kisser.
- Department of Redundancy Department / Malaproper: Tends to speak using both of these.
- Evil Principal: He hates the children of his school and his Evil Plan is funded with money he scammed out of the school's budget.
- Insane Troll Logic: On various occasions, most memorably when he asks whether Max wants him to give his car to a smelly goat, and then insists that the goat will never take his car.
- Small Name, Big Ego: He's a tremendously self-important idiot who tries to come off as tough and intimidating but mostly just comes off as immature and incompetent.
Troy McGinty
Portrayed by: Noel FischerCurtis Junior High's resident bully wears a shirt with the name of the kid he's gonna torture each day.
- The Bully: Wears a shirt with his daily victim carved into it.
- Evil Redhead
- We Used to Be Friends: Him and Max 8 years before the start. They didn’t really have much of a falling out; as Max explains they went in different directions in life. Max even greets him in a friendly manner at first.
- Why Did It Have to Be Snakes?: The reason Troy fell out with Max is because when they were young, Troy got scared of the character Macgoogles the Highland Frog, resulting in all their friends laughing at him. Even as a teenager, Troy is scared of the frog.
Evil Ice Cream Man
Portrayed by Jamie Kennedy. Exactly What It Says on the Tin, his goal is to get revenge on Max for Max's mom ratting him out to the health department after Max finds a cockroach in an ice cream cone.
- Bad Humor Truck: In the opening dream sequence, it has a cannon. In reality, he chases after Max with it when he is going to school on his bike with the apparent intent of running him over.
- Disproportionate Retribution: And Misplaced Retribution, too. He terrorizes little kid Max over a crime that the kid's mother denounced and he probably would have prevented from happening if he spent less time being a Jerkass to keep his truck clean.
- Large Ham: Probably the hammiest ice cream man in fiction.
Jenna
Portrayed by: Brooke Anne Smith
Max's dream girl, Jenna is a classmate a few grades above him, and is one of the people on Max's newspaper delivery route.
- Alpha Bitch: Max's crush, and his best friend Megan's worst enemy. Played with in that Jenna is more of a Brainless Beauty who's so shallow that she doesn't realize she's being mean.
- Almost Kiss: In Max's dream. After Max hands her the newspaper, Jenna bends down towards Max as she puckers her lips up to kiss him. Unfortunately, the moment is ruined when the Evil Ice cream man fires a scoop of mint flavored ice cream at Jenna's face, right as Max awakens from his dream.
- Dull Surprise: How she tends to speak.
- Flat Character: Aside from being the object of Max's desires and her brief rivalry with Megan, there is literally nothing more about her character that is brought up.
- Girl of My Dreams: Literally, Max dreams about her in the opening scene. Their exchange during the dream suggests that they are a couple and ends with an Almost Kiss between them.
- Hair Flip: She is shown flipping her hair whenever she makes an appearance.
- Hair of Gold, Heart of Gold: Averted. She is not as nice as she is in Max's dreams.
- Head-Turning Beauty: Max is so entranced by her that he ends up walking into a door.
- Leitmotif: Jenna has one that plays every time she appears. It's the intro to Britney Spears' "...Baby, One More Time"
- Long Hair Is Feminine: She is always shown wearing her hair down.
- Loving a Shadow: She starts to show interest in Max when he becomes popular for his actions at school. When said actions lead to certain school activities being cut, she reveals that she never liked him and only viewed him as a paperboy. She switches again when Max gets popular again for standing up to the bullies, but by this point, Max can see that she only wants to hang with him because he was popular.
- Lust Object: For Max. He gets extremely flustered whenever she is within his vicinity. She ends up using this to her advantage later when she seduces him into coming to a party with her.
- Ms. Fanservice: She's usually seen wearing tight cleavage revealing tops, tight pants and short skirts, which often causes Max to distracted and flustered around her. Not to mention she's about three years older than Max and his friends.
- One Head Taller: She is this with Max, since the boy hasn't hit puberty yet.
- Pink Is Erotic: In Max's dream's, she is shown wearing a pink tank top.
- Romantic False Lead: The trailers and the first act of the film sets her up to be the Love Interest to Max, but it becomes clear that she doesn't like Max at all as the film progresses.
- Sexophone: A sexy jazz saxophone tune plays when she first appears in Max's dreams.
- Show Some Leg: Upon running into Max as he is heading to his friend's going away party, Jenna invites him to go get a milkshake. Max tries to decline saying that he has to be somewhere, but she pushes on, telling him to come for one milkshake. When Max is still hesitant, she bends down to him, saying one milkshake. Flustered by her flirting and her figure, he ultimately accepts. As they walk down the street, Jenna continues her manipulation by putting her arm around him before playing with his hair.
Caption Writer
(Portrayed by Justin Berfield)
- Mr. Exposition : Introduces all the bullies to Worried Kid.
- Punch-Clock Villain: Not outright malicious, just good at what he does.
- School Newspaper News Hound