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.
- Ear Worm: The Sammy Squirrel theme song. Even Dr. Frankenstein, who hates the character and song, can't stop humming it to himself at one point, exclaiming "I can't get that song out of my head!"
- Extremely Short Timespan: The movie is set over a period of three days.
- 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.
- Laser-Guided Karma: Dr. Frankenstein hates Sammy Squirrel. His comeuppance is getting stuck in a Sammy Squirrel suit and being forced to play the character at the park.
- 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.
- Oh, Crap!: Simon when he realizes three minutes have passed since Alvin was given Cartoon Monster Maker Frappe, causing it to take its full effect.
- Papa Wolf: When Mr. Yesman threatens to blacklist the boys after learning they haven't showed up to the premiere, Dave calmly, yet defiantly defends the boys, saying that "they're not monsters".
- Punctuated! For! Emphasis!: "Don't. Touch. The cap."
- Roundabout Shot: One of these occurs during the "If You Wanna Have Friends" montage as the Chipmunks and the children dance around Frankie.
- Shout-Out: See the main shout out page for the franchise.
- 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.