Between 1999 and 2005, Bagdasarian Productions released three [[DirectToVideo direct-to-videos]] based on the '80s ''WesternAnimation/AlvinAndTheChipmunks'' series.

The second one came out in 2000, an animated horror-themed film entitled ''Alvin and the Chipmunks Meet the Wolfman''. Like the previous direct-to-video, it was produced by [[Creator/{{Universal}} Universal Animation Studios]], animated by Creator/TamaProductions, and distributed by Universal Studios Home Entertainment.

Alvin thinks of himself as an expert on spooky stuff such as vampires and werewolfs, so when a mysterious stranger moves in next door, Alvin's convinced he's a werewolf. Then, when Theodore gets bitten by a "dog", he starts chewing socks, eating meaty stuff, and is a lot faster, even Simon thinks something's not right. But at the moment, he's more like a werepuppy. They now have to find a way to cure him before the next full moon, during the school play, ''Dr. Jekyll and Mr. Hyde'', or else Theodore will become a werewolf forever!

'''NOTE:''' ''Tropes under here are '''specifically''' for the 2000 DirectToVideo movie''.
* Tropes exclusive to the [[SeriesFranchise whole franchise]] go in ''Franchise.{{Alvin and the Chipmunks}}'';
* Tropes exclusive to the [[UsefulNotes/TheDarkAgeOfAnimation '60s cartoon]] series go in ''WesternAnimation/TheAlvinShow'';
* Tropes exclusive to the [[UsefulNotes/TheRenaissanceAgeOfAnimation '80s cartoon]] series go in ''WesternAnimation.{{Alvin and the Chipmunks}}'';
* Tropes exclusive to the [[AnimatedAdaptation 1987 animated]] film go in ''WesternAnimation/TheChipmunkAdventure'';
* Tropes exclusive to the other DirectToVideo[[invoked]] movies go either in:
** ''WesternAnimation/AlvinAndTheChipmunksMeetFrankenstein'';
** ''Film/LittleAlvinAndTheMiniMunks'';
* Tropes exclusive to the [[LiveActionAdaptation live action/CGI]] movies go in ''Film.{{Alvin and the Chipmunks}}'';
* Tropes exclusive to the [[WesternAnimationOfThe2010s 2015 cartoon]] series go in ''WesternAnimation/ALVINNNAndTheChipmunks''.


* AllGirlsWantBadBoys: Subverted with Eleanor. She start to dislike the new Theodore because too smug and arrogant.
* AntiHero: The Wolfe-fied version of [[spoiler:Theodore plays as a [[NominalHero Type V]].]]
* AscendedExtra: Eleanor is a variation of this. She was often overshadowed and underused throughout the franchise, particularly [[WesternAnimation/AlvinAndTheChipmunks the '80s cartoon series]], though in this movie, considering that much of the plot focuses on Theodore, being his [[DistaffCounterpart counterpart]], she gets quite a bit of exposure.
* AsideGlance: Alvin gives a quick one after Simon explains the DeusExMachina way Theodore is cured.
* AttentionWhore: Brittany. She not take well when find that, in the school play, her role is the tree. Indeed she take advantage of the play when the kids are forced to improvise.
* BareYourMidriff: During the Jekyll-Hyde wrap party, Eleanor wears a skimpy little outfit that exposes her navel... it's a wonder she weren't reprimanded for possibly violating any school dresscodes. Britney also wears something similar midway through the movie
* BigBrotherInstinct:
** Early on, Alvin pulls a prank on the main bully for harassing Theodore. It's the only positive thing that Principal Milliken can say about him.
** A brief moment with Brittany when Theodore is rude to Jeanette.
* BigDamnHeroes: [[spoiler:Despite Theodore's transformation, he manages to retain enough of his senses to fight off Talbot!Wolfman in order to protect Eleanor from the older Wolfman.]]
* BigNo: By Alvin after Dave confiscates his monster stuff and fires him from the play. Later transitions to Mr. Rochelle who says the same thing. Both accompanied by a SkywardScream.
* TheCameo: Miss Miller's only scene in this movie is her [[MamaBear yelling at Dave]] over the phone after Alvin scares the Chipettes.
* TheCavalryArrivesLate: [[spoiler:Dave witnesses Talbot transform into a werewolf and rushes to warn the school, but bumps into a pole and falls to the ground unconscious. Then after the climax, when comes to, and arrives at the school, everything's already back to normal.]]
* ChekhovsGun: Theodore gives Eleanor a necklace just before he gets bitten. [[spoiler: When he transforms into a werewolf during the play and is about to attack Eleanor, he catches sight of the necklace and remembers enough of himself to stop.]]
* TheCloudcuckoolanderWasRight: Everyone, Simon especially, thinks Alvin's theories about a monster in their midsts are insane, and to be fair he has [[CryingWolf a track record for such accusations]], [[spoiler:but the very person he suspected of being a werewolf turned out to be one.]]
* CrazyPrepared: It turns out the school board managed to establish a special grant to cover any damages caused by Alvin's pranks.
* CreditsGag: Mr. Talbot is listed in the credits as "Mr. Talbot, the Wolfman".
* DamselInDistress: Eleanor near the end of the film when she is attacked by Talbot.
* DancePartyEnding: The Chipmunks and Chipettes end the wrap party by performing "Everything's Gonna Be Alright", and soon everyone else follow the rhythm.
* InvoluntaryShapeshifter: [[spoiler:Dave finds out the hard way...]]
* IveGotAnXAndImNotAfraidToUseIt: "I've got a lemon zester and I'm not afraid to use it!" Said by the Chipmunks' neighbor when Simon and Alvin accidentally wake him up, while they go after werewolf-transformed Theodore as he escapes the house and they try to get him back.
* MagicPants: [[spoiler:Both Theodore and Mr. Talbot.]]
* NotHimself: After gets bitten by the "dog", Theodore became very strong and cool during the day, but also arrogant and aggressive. To point that Brittany ask if he and Alvin have a FreakyFridayFlip.
* LegacyCharacter: It's implied that Mr. Talbot [[spoiler:is a descendant of Lawrence Stewart "Larry" Talbot, the main character of Universal's original series of ''[[Film/TheWolfMan1941 Wolf Man]]'' films.]]
* OOCIsSeriousBusiness: Theodore is a vegetarian. So when he asks if there is a steak sandwich in his lunch bag, a puzzled Dave reminds him that he doesn't eat meat.
* OminousFog: Brittany even comments on how much she dislikes the particular kind of weather at one point.
* OurWerewolvesAreDifferent: Theodore as a [[{{Pun}} weremunk]] and Mr. Talbot. [[spoiler: At the end, Theodore cures them both by biting Mr. Talbot, which caused the effect to reverse on both of them]].
* PlayingATree: The school is putting on a play about Dr. Jekyll and Mr. Hyde. Brittany thinks she's playing "a girl named Willa who cries a lot". She's a weeping willow.
* SharpDressedMan: The Chipmunks' new neighbor, [[NameDrop Mr. Talbot]].
* ShipTease: Theodore shows a lot of affection for Eleanor in the movie, and in the climax [[spoiler: he's stopped from attacking her when he sees the necklace he gave her earlier.]]
** Also, when Theodore does his EvilLaugh during rehearsals, Alvin and Brittany [[SecurityCling hold each other]], shaking.
* ShoutOut: See the main [[ShoutOut/AlvinAndTheChipmunks shout out page]] for the franchise.
* ThrowItIn: In-universe, the play goes off the rails when [[spoiler:Theodore transforms]] and the kids are forced to improvise, such as Simon and Jeanette acting out a scene where Jekyll has apparently split into two people, a set of twin sisters, and [[ItMakesSenseInContext some of the potion splashes onto a tree, bringing it to life]]. During the after party, the director takes credit for everything the kids made up, though Principal Milliken just responds to everything he says with a dismissive "Uh-huh."
* TransformationSequence: Simon has the honor being front-row center for [[spoiler:Theodore]]'s transformation.
* TrailersAlwaysSpoil: Also counts as a Covers Always Spoil as well since both show [[spoiler:Theodore as a werewolf.]]
* VocalDissonance: Not a big deal, but in the Mexican Spanish dub of the movie, the Chippettes are given voices that would be more befitting for a teenage woman.
* WolfMan: Not only Lawrence Talbot, but Theodore becomes a weremunk as well.
* YoungerThanTheyLook: Principal Milliken is only 31, but looks 50, due to the stress of dealing with Alvin for so long that she retires at the end of the movie.