The first one is Alvin and the Chipmunks Meet Frankenstein, a horror-themed animated film that came out in 1999 produced by Universal Animation Studios, animated by Tama Productions, and distributed by Universal Studios Home Entertainment.
While the Chipmunks are working in a famous movie studio park called Majestic Studios in a singing attraction, the real Dr. Frankenstein comes to work in the studio's most famous attraction, Frankenstein's Castle. After Alvin drives a crazy bus chase, they miss their next performance and get locked in the studio after closing time. Dr. Frankenstein figures the castle is not scary enough so he re-builds the real Frankenstein. IT COMES ALIVE! So it finds the boys and starts a wild and scary adventure!
NOTE: Tropes under here are specifically for the 1999 Direct-to-Video movie.
- Tropes exclusive to the whole franchise go in Franchise.Alvin and the Chipmunks;
- Tropes exclusive to the '60s cartoon series go in The Alvin Show;
- Tropes exclusive to the '80s cartoon series go in WesternAnimation.Alvin and the Chipmunks;
- Tropes exclusive to the 1987 animated film go in The Chipmunk Adventure;
- Tropes exclusive to the other Direct-to-Video movies go either in:
- Tropes exclusive to the live action/CGI movies go in Film.Alvin and the Chipmunks;
- Tropes exclusive to the 2015 cartoon series go in ALVINNN!!! and the Chipmunks.
Now has a shout out page.
- Actor Allusion: This is the second time Michael Bell has played a character who built a humanoid being: The first one was Clockwork Smurf as Handy Smurf.
- Adaptational Villainy: Victor Frankenstein is portrayed as a Card-Carrying Villain who abducts Alvin to change him into a monster when he is upset by the original monster's Gentle Giant nature, and at one point threatens to eat people.
- Big "NO!": Alvin screams this as Dr. Frankenstein feeds him the frappe.
- Denser and Wackier: There's more slapstick, and goofy humor in this movie than in previous Alvin and the Chipmunk incarnations.
- Earworm: The Sammy Squirrel theme song.
- Family-Unfriendly Death: The Chipmunks bury an imaginary Frankenstein's Monster alive while singing "Will make this place his tomb!" during their "What If a Monster Came into Our Room" song. This is before they realized the Frankenstein's Monster that was chasing them happened to be a gentle giant.
- Frankenstein's Monster: Duh.
- Gentle Giant: Again, the Frankenstein's Monster.
- I'm a Humanitarian: Early on, Victor threatens to eat the park visitors in his lab unless they scram.
- This Is No Time for Knitting: Simon listing off things they need to save Alvin, Buffy Speak style. Theodore goes to the snack table, to get the items Simon was asking for.
- Mad Scientist Laboratory: In a castle... at an amusement park no less!
- Musical World Hypothesis: The three songs in the film follow this order: Diegetic, Alternate Universe, All In Their Heads.
- Mythology Gag: When the Chipmunks' faces are distorted by fear and g-forces in the runaway roller coaster, they are for a brief moment turn to how they appeared in The Alvin Show, then to "realistic" looking chipmunks as on their first album covers before returning to their normal selves.
- Punctuated! For! Emphasis!: "Don't. Touch. The cap."
- Shout-Out: See the main shout out page for the franchise.
- Suddenly Voiced: Frankie goes from making throaty noises to being capable of speaking properly. See Vocal Dissonance below.
- Toon: What Dr. Frankenstein managed to turn Alvin into when trying to turn him into a monster, a little cartoon troublemaker.
- Vocal Dissonance: At first, Frankie's only able to utter deep, moaning noises. By the time he learns to speak properly, he talks in a high-pitched, squeaky voice just like the Chipmunks. Must have something to do with the fact the Chipmunks themselves taught him how to speak.