Moviegoers who enjoy musicals, comedies, and cute mischievous chipmunks are likely big fans of the Alvin and the Chipmunks movie franchise. In the series, three chipmunk brothers — Alvin, Simon, and Theodore — bring a whole new level of fun and hilarity as they navigate their way through life, all while trying to make it big in the music industry.
The three chipmunks and their human caregiver provide a one-of-a-kind blend of comedy, music, and heartwarming narrative. The films are not only intended for children since Alvin and the Chipmunks subtly explores relevant issues beneath the fun and frolic. Family, friendship, the trials of young adulthood, and the difficulty of satisfying both one’s own needs and those of one’s community are just some of the themes explored in the show.
Moreover, the films’ ageless humor can also appeal to adults. Those interested in an Alvin and the Chipmunks marathon can watch the eight films in any sequence. Still, we recommend watching them chronologically to eliminate plot holes, and here’s how.
1. Alvin and the Chipmunks (2007)
The first film on the list is Tim Hill’s live-action/animated Alvin and the Chipmunks from 2007. In the movie, we meet the talented chipmunks Alvin, Simon, and Theodore as they deal with the loss of their tree and subsequent relocation to Los Angeles. Once the tree is on exhibit in the city, the chipmunks run into David Seville (Jason Lee), a struggling musician who hears their music and hires them. Dave is so impressed by the chipmunks’ singing that he forms a band with them and gives them the name “Alvin and the Chipmunks.”
Ian Hawke (David Cross) — a ruthless music businessman — takes the group under his wing as they become an overnight hit and uses them for his own gain. The film follows the Chipmunks as they struggle to stay close to Dave and each other despite the stresses of making it big in the music business. Despite their newfound success, the Chipmunks know nothing is more important than their friendship with Dave. This realization propels them to risk everything to save Dave from Ian, who takes him hostage. The success of Alvin and the Chipmunks led to the creation of several more films starring the endearing trio. The soundtrack — which features the Chipmunks’ distinctive high-pitched interpretations of popular songs — also did quite well commercially.
2. Alvin and the Chipmunks: The Squeakquel (2009)
The 2009 film Alvin and the Chipmunks: The Squeakquel is the sequel to the live-action/animated Alvin and the Chipmunks from 2007. Betty Thomas takes the director’s chair to oversee the ever-entertaining Alvin, Simon, and Theodore’s next adventures. In The Squeakquel, Dave gets hurt at a benefit performance and is taken to a hospital in Paris, leaving the chipmunks in the care of Toby (Zachary Levi), his inept cousin.
The chipmunks then have the added challenge of preparing for the Battle of the Bands while struggling with typical teen problems like sports, cliques, and even love interests – creating countless funny scenarios. Also making their debut in The Squeakquel are The Chipettes – a trio of female chipmunks comprised of Brittany, Eleanor, and Jeanette. Like the Chipmunks, the Chipettes fall victim to Ian Hawke – the conniving former JETT Records executive who has fallen on hard times since the first film’s events. Charmingly and amusingly, the film weaves together the stories of the Chipmunks and the Chipettes, who start competing in a musical war that quickly escalates into a battle of the sexes.
3. Alvin and the Chipmunks: Chipwrecked (2011)
Third in the live-action/animated film series starring the chipmunks, Alvin and the Chipmunks: Chipwrecked follows the misadventures of Alvin, Simon, and Theodore, along with their female equivalents, the Chipettes – who return in this 2011 film directed by Mike Mitchell. The plot centers around a vacation cruise that goes wrong. The Chipmunks, Chipettes, and their guardian — Dave — board a luxury cruise ship for some relaxation. Their vacation, however, takes a wild turn when the ever-mischievous Alvin accidentally sets off a chain of events that leaves them all stuck on a deserted island.
The island journey has its share of thrills and perils, putting the chipmunks’ survival abilities to the test. They search for food, explore the island, and encounter a potential volcano eruption. Meanwhile, Dave searches for the missing Chipmunks and Chipettes with the reluctant help of former record executive Ian Hawke. One intriguing subplot includes Simon discovering a peculiar necklace that causes him to act differently and adopt the daring alter-ego “Simone,” resulting in an unusual interaction between him and the others, particularly Alvin.
4. The Chipmunk Adventure (1987)
Directed by Janice Karman and produced by Ross Bagdasarian Jr. — the son of Ross Bagdasarian Sr., who originally created The Chipmunks in the late 1950s — The Chipmunk Adventure is a 1987 American animated musical film that sees the Chipmunks and the Chipettes pitted against one another in a hot-air balloon race across the world by Claudia and Klaus Furschtein, two diamond smugglers who are up to no good. The siblings believe they are participating in a charity race they organized.
Unbeknownst to them, the diamond smugglers are using the race as a cover to deliver diamonds to various locations worldwide. The Chipmunks and Chipettes go on many exciting adventures, from evading a gang of locals in Borneo and saving a baby penguin in Antarctica to escaping a band of Arabian princes who mistake Brittany for a princess. The movie’s many musical numbers — in which the Chipmunks and Chipettes show off their singing and dancing skills — are among its many highlights. Favorite film tunes include “The Girls of Rock’ n’ Roll,” “Off to See the World,” and “Diamond Dolls.”
5. Alvin and the Chipmunks: The Road Chip (2015)
The live-action/animated feature Alvin and the Chipmunks: The Road Chip is the fourth in the series. Walt Becker directed the 2015 film about the Chipmunks’ antics on a road trip throughout America. They set out to stop their father figure, Dave, from proposing to his new fiancée Samantha (Kimberly Williams-Paisley) in Miami and abandoning them. Joining the adventure is Samantha’s teenage son, Miles (Josh Green), who, like the Chipmunks, is not thrilled about the potential union of their parents.
From an overzealous air marshal (Tony Hale) to a legendary bar fight in Texas, their trip to Miami is full of humorous misadventures and hurdles. The journey brings about character development and bonding for both Miles and the chipmunks. The Chipmunks learn valuable lessons about the meaning of family, and they eventually accept that Dave will always love them, even if he finally settles down with a wife and starts a family.
6. Alvin and the Chipmunks Meet Frankenstein (1999)
The animated film Alvin and the Chipmunks Meet Frankenstein premiered on home video in 1999. Filmmaker Kathi Castillo brings something new to the Alvin and the Chipmunks series with this entry, which successfully blends horror aspects with the film’s family-friendly tone. The action kicks off with a performance by Alvin, Simon, and Theodore in an amusement park based on the film industry called Majestic Movie Studios. However, Alvin’s shenanigans quickly get them into hot water, and they end up stranded in the park after hours. When they visit the park’s scary attraction, they are shocked to learn that it isn’t fake and that the famed horror character Frankenstein’s monster has been brought back to life by an ambitious doctor.
The Chipmunks don’t find the monster frightening; they find him to be a pleasant fellow who’s just a little disoriented in the modern world. They decide to help the creature, who they’ve fondly named “Frankie,” and strive to protect him from the greedy and evil scientist who wants to use him for his own gain. However, after experiencing the monster’s lifestyle, Alvin finds himself in a more problematic situation. Following the failure of an experiment, Alvin takes on the demonic traits of a classic monster, wreaking havoc and causing distress for Simon, Theodore, and Frankie.
7. Alvin and the Chipmunks Meet The Wolfman (2000)
In 2000, director Kathi Castillo brought us the animated feature Alvin and the Chipmunks Meet the Wolfman. Like its predecessor, Alvin and the Chipmunks Meet Frankenstein mashes the original cast and themes with traditional horror stories. Alvin, Simon, and Theodore are living a regular life when they start to suspect that their new neighbor, Mr. Talbot, is actually a werewolf and embark on an exciting expedition to prove it. Alvin, in particular, is obsessed with late-night monster movies, and his imagination runs wild, instilling fear and excitement in his brothers.
As the brothers continue their inquiry, Theodore is bitten by a dog (which they suspect is Mr. Talbot in his werewolf form). He begins to exhibit weird behavior, including an increased appetite, remarkable strength, and growing fangs. The brothers, particularly Alvin, grow increasingly concerned that Theodore is transforming into a werewolf. In the meantime, the Chipmunks are also busy preparing for a play, Dr. Jekyll and Mr. Hyde, which runs parallel to the current events and adds another dimension of comedy and drama to the story.
8. Little Alvin and the Mini-Munks (2003)
Directed and produced by franchise co-owner Janice Karman, Little Alvin and the Mini-Munks takes the series in a new direction by depicting the Chipmunks and Chipettes as little children. This DTV release stands out from the rest of the series since it combines puppetry and animation instead of just the latter. It’s also unusual since it moves the protagonists out of their usual milieu of rock stardom and into an average home’s more grounded, everyday setting.
The “Mini-Munks” — younger versions of Alvin, Simon, Theodore, Brittany, Jeanette, and Eleanor — spend most of the film at the house of a kind human figure named La-Lu. La-Lu’s house is full of enchantment, from the talking parrot Gilda to the stuffed bear Talky Teddy. Little Alvin and the Mini-Munks does not have a linear plot. It is more of an anthology than a single story, with episodes focusing on topics such as sharing, facing fears, and the value of cleanliness – issues relevant to kids.