The Chipmunk Adventure
A pair of Europeans running international diamond smuggling ring, running out of ways of delivering $5 million of diamonds to customers without government interference. Both find an opportunity when they overhear Alvin and Brittany arguing over who would win an actual race around the world, to which the Furschtein have the Chipmunks and Chipettes travel in different directions around the world in hot air balloons, stopping at twelve different locations, where they would deliver a doll of themselves full of diamonds and receive a doll of the other team full of money. This is in hopes that [Inspector] Jamal won't expect them.
- Big Bad Duumvirate: The main antagonists of The Chipmunk Adventure.
- Big Fancy House: Their estate is absolutely sprawling, with an enormous mansion, pool and garden with a huge fountain.
- Brother–Sister Team: A villainous version alongside Klaus.
- Cool Car: Their Rolls-Royce Silver Cloud I
- The Mole: Their butler Mario has been reporting information about them to Jamal.
- It Amused Me: This is the reason Klaus gives the Chipmunks and Chipettes for the two of them supporting this race around the world, claiming, "We're quite wealthy and very bored."
- Noodle Incident: How they tried delivering diamonds to those who are part of the smuggling ring but were stopped:Claudia: Don't forget, dear brother, Jamal robbed us three million dollars of priceless . . . precious . . . gorgeous, spectacular . . . to die for gems!
(Claudia and Klaus overhear Alvin and Brittany arguing who would win a race around the world to which Claudia gets the idea to use them [Chipmunks & Chipettes] to which Klaus refuses)
Claudia: Listen to me, Klaus! If you think I'm going to make you botch up this deal, like you did the last one . . .
Klaus: Must you keep reminding me? I underestimated Jamal! It won't happen again!
Claudia: You bet it won't! We're doing things my way this time! - Obviously Evil
- Siblings in Crime
- Smoking Is Cool: Claudia even takes a whiff of smoke and holds it while giving a "I'm cool" posture before she starts coughing.
Claudia Furschtein
A diamond smuggler of German decent alongside her brother, Claudia is very attached to her dog, Sophie and takes her everywhere.
- Evil Laugh: This follows after the line "Jamal will never expect [the Chipmunks and Chipettes] in a million years!"
- Large Ham: Being voiced by Susan Tyrell will definitely have that effect.
Klaus Furschtein
A diamond smuggler of German decent alongside his sister, Klaus doesn't have a good relationship with Claudia's dog Sophie and constantly try to make the other look bad in front of Claudia.
- Butt-Monkey: Suffers at the paws of Sophie.
- Even Evil Has Standards: At first, adamant about having the Chipmunks and Chipettes deliver their wares when he and Claudia overhear Alvin and Brittany saying, "it's too dangerous" and "they're only children" arguing but quickly gives in when Claudia decides to do things her way.
Sophie
Claudia's small dog who enjoys annoying Klaus, Sophie is believed to be a Yorkshire or Silky Terrier.
- Bitch in Sheep's Clothing: Perceived to be nice at the beginning, but proves to be as coldhearted as Claudia such as ripping Klaus' designer clothes and popping his floating pool chair for him getting water on her.
- Mister Muffykins: An extremely pampered, spoiled dog with a mean streak.
- Playing the Victim Card: After deflating Klaus' pool chair, Sophie goes into dramatics as Claudia's attention returns.
A shady looking character who has two men named Cisvan and Cuomo working for him, Jamal seems to know Claudia and Klaus Furschtein. It's revealed he's an inspector working for INTERPOL and been working to bust the illegal international diamond smuggling ring run by Claudia and Klaus and been trying to put them into custody for years.
- Chair Reveal: How he's introduced.
- The Determinator: Been going after the siblings for years.
- Good All Along: He is a inspector, part of INTERPOL Los Angeles Devision.
- Sharp-Dressed Man
- Obviously Evil: Subverted. Sends his two goons after the Chipmunks and Chipettes when he's first introduced but it's revealed he's on their side and only wants them safely returned home.
- Villainous Gold Tooth: He has a gold tooth that's constantly accompanied by an Audible Gleam. The sinister implication is subverted after it's revealed that Jamal is not villainous, but actually an INTERPOL agent.
- Bumbling Henchmen Duo: Jamal's incompetent minions who are seldom apart.
- Butt Monkeys: Had a very hard time trying to capture both Chipmunks and Chipettes.
- Good All Along
- You Have Failed MeJamal: You imbeciles, I ask you to take candy from a baby and you fail me miserably!
A very young prince who has the Chipettes kidnapped by Inspector Jamal's request and tries to make Brittany one of his wives.
- A Child Shall Lead Them: He is very young but appears to have authority.
- Interspecies Romance: He decides to keep Brittany in his palace and marry her when they come of age in a decade or so.
- Royal Brat: Very spoiled and demanding to his advisors.
- Vague Age: He is a child but it's never stated how old he is.
- Villainous Respect: Brittany endears herself to him by screaming to be released.
A group of Natives who kidnapped Theodore when he and his brothers decided to camp in a jungle on Howland Island while taking a shortcut, crowning him "Prince of Plenty" and force Alvin and Simon to serve him.
- Appease the Volcano God: What they planned to do to Theodore (along with Alvin and Simon) during the full moon by feeding them to a pit of crocodiles as Simon and Alvin find out by reading a series of ideograms on the walls of a cave.
- Hollywood Natives: An African tribe whose members wear loin cloths, don Tribal Face Paint, and have Savage Piercings.
- God Guise: Mistake Theodore for their 'Prince of Plenty.'
- One-Gender Race: No women are seen...
Alvin and the Chipmunks Meet Frankenstein
As his last name may hint, Frankenstein is a mad scientist who inhabits the new attraction "Frankenstein's Castle" at the Majestic Movie Studios where he makes another monster. When he spots the Chipmunks (who, not only missed their own show, but are locked inside the theme park) spying on him, Frankenstein sends his creation after them, though when later tracking the creature, Frankenstein spots him at the Sevilles' home, and, angered at the monster's benevolence kidnaps Alvin to make the red-clad Chipmunk into his new monster.
- Adaptational Villainy/Card-Carrying Villain: Portrayed as such who abducts Alvin to change him into a monster when he is upset by the original monster's Gentle Giant nature.
- Bald of Evil
- Creating Life
- Herr Doktor
- Irony: Really hates the theme park Sammy Squirrel mascot, but is forced to sneak inside the premiere dressed as Sammy Squirrel in hopes to change Alvin back into a monster but unfortunately is electrocuted and is stuck in the Sammy Squirrel costume.
- No Brows
- Mad Scientist: Much more so than Crashcup.
A monster created by Doktor Frankenstein, who eventually befriends the Chipmunks.
- Big Damn Heroes: Along with Theodore and Simon, little late to save Alvin from the potion forcibly given to him by Doktor Frankenstein that'll make him into a zany cartoonish monster but does rescue him before the process could be completed.
- Toward the end of the film, a disguised Frankenstein sees Alvin (who was transformed into a zany cartoon monster by the mad doctor but couldn't finish the process) back to normal but realizes if he shocks Alvin he will cause the Chipmunk to change back, so the doctor turns Alvin's microphone to a high revere. Cue Frankie showing up and grabbing the doctor. As the Frankenstein Monster carries his creator, Frankie slips and Dr. Frankenstein grabs the microphone to steady himself, only to be shocked. This also exposes himself to the public, but the Chipmunks (mainly Theodore) come to his rescue.
- Captain Ersatz: Basically the animated version of Universal's Frankenstein Monster played by Boris Karloff.
- Drives Like Crazy: As a result of Alvin teaching him how, he drives tourists around the sets in a bus rather recklessly.
- Frankenstein's Monster
- Gentle Giant
- Heel–Face Turn: When becoming friends with the Chipmunks.
- Evil Minions: For Frankenstein at first.
- In-Series Nickname: Is called "Frankie" by the Chipmunks, mainly Theodore.
- Manchild
- No Brows
- Suddenly Voiced: Is given a voice in the final scene, though it's a Chipmunk voice.
- The Unintelligible: At least toward the end.
- Vocal Dissonance: In the end when he finally speaks, he talks like a Chipmunk.
The neurotic, overworked overseer of the Majestic Movie Studios theme park (a parody of Universal Studios Hollywood).
- Nervous Wreck: He's so in fear of losing his job that he often unloads his problems on Dave.
- Unwitting Instigator of Doom: In a desperate attempt to make the Frankenstein's Castle attraction scarier, he hires the real Dr. Frankenstein.
An aspiring actor who serves as the tour guide/bus driver at Majestic Movie Studios.
Alvin and the Chipmunks Meet the Wolfman
The Seville's next door neighbor, Lawrence Talbot, as his name may suggest is also a werewolf who bites Theodore, turning him into a werewolf as well. Though after both are cured of their lycanthropy, Talbot becomes the new principal of Clyde C. Crashcup Elementary School.
- Being Evil Sucks: He hated being under the curse of the werewolf, as evidenced by him thanking Theodore for curing him.
- Big Ol' Eyebrows
- Credits Gag: Listed in the credits as "Mr. Talbot, the Wolfman".
- Expy: Of Lon Chaney, Jr.'s Larry Talbot character.
- Involuntary Shapeshifter: During the night of the full moon, which happens at the same night of the Chipmunks' and Chipettes' school play.
- Mark of the Beast: Appears when he faces his palm to the full moon while talking to Dave, just before he starts transforming.
- Sharp-Dressed Man
- The Stoic
- Took a Level in Cheerfulness: During the wrap party, he picks a dance with Madame Raya.
- Wolfman: A classic wolfman, if not the classic. At the end, Theodore cures them both by biting Mr. Talbot, which caused the effect to reverse on both of them.
The very flamboyant and overly melodramatic drama director at Clyde C. Crashcup Elementary School, Mr. Rochelle is a member of the Elementary School Theatrical Directors' Bowling League.
- Always Camp
- Flamboyant Gay: Bursts into hysterical tears when told Alvin couldn't be Mr. Hyde.
- Large Ham
The principal of Clyde C. Crashcup Elementary School until she goes into early retirement as principal and takes a job "driving trucks full of nitroglycerin across rickety bridges in South America".
- Younger Than They Look: The stress of dealing with Alvin for so long has done this to her.Dave: You don't look a day over fifty.Milliken: I'm thirty-one!
A bully who looks like he had been held back a year or two, Nathan takes pleasure in tormenting Theodore, though he does suffer retaliation from Alvin.
- The Bully: For Theodore.
- Establishing Character Moment: The first time we see Nathan, he's threatening Theodore with physical harm for doing his job as sound effects person for the play.
- Heel–Face Turn: He stops harassing Theodore after Theodore shows compassion following Nathan attempting to humiliate him.
- Kids Are Cruel
- Laser-Guided Karma: Bullying Theodore will more often than not result in Alvin standing up for him, usually with a prank.
- Only One Name: He is not given a surname.
Madam Raya is the host of a television monster movie special first seen in an ad for her book, The Monster Book of Monster Facts. Alvin and Simon seek her out at the TV station to ask for help with changing Theodore back from a werechipmunk.
- The Cameo: Seen at the end of the movie dancing with Lawrence Talbot at the wrap party for the school play.
- Con Man
- Deadpan Snarker
- Expy: Likely one to Elvira, Mistress of the Dark.
- Gag Nose
- Our Lawyers Advised This Trope: In promoting her book, "you must be eighteen to call, but don't worry, we don't ask."
