The merge between pop music and the film industry has gone through its various stages in the last few decades, but none as peculiar yet extremely catchy as the reputation and career of Alvin and the Chipmunks. The sensational trio of Alvin, Simon, and Theodore premiered for the first time on film in 1987 in the movie The Chipmunk Adventure. Since then, the fictional band of chipmunk brothers has gone on to be the main focal point in both animated and live-action movie adaptations, establishing a beloved franchise. The live-action movies in particular garnered the attention of the public with some familiar names voicing the singing chipmunks, such as Justin Long as Alvin, Matthew Gray Gubler as Simon, and Jesse McCartney as Theodore.
Now you may be wondering: How could 3 animated chipmunks impact the film and music industry at all? Well, the fictional trio practically went viral when “Chipmunk Versions” of songs became an ongoing trend after the first live-action movie was released in 2007. Not to mention that the animated and live-action depictions of Alvin and the Chipmunks became an iconic and very nostalgic franchise for people of all ages — and it just gets better with time. Check out our ranking of every movie in the franchise so far.
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8 Alvin and The Chipmunks: The Road Chip

Everyone loves a road trip movie, right? The theatrical live-action trilogy of Alvin and the Chipmunks films were hits for modern generations. Alvin and the Chipmunks: The Road Chip was the fourth live-action movie and was released in 2015. By this time, four years since the first live-action movie was released, it’s fair to say that audiences were kind of over it. This movie follows Alvin, Simon, and Theodore as they attempt to stop Dave, played by Jason Lee, from proposing to his girlfriend Samantha, played by Kimberly Williams-Paisley.

7 Alvin and the Chipmunks: Chipwrecked

Every time a movie is added to a franchise, you should expect writers to raise the bar in terms of what these well-established characters go through. Alvin and the Chipmunks: Chipwrecked was not a favorable movie in the franchise, and it was obvious that the momentum of the first two movies was fizzling out. However, the change of scenery and the somewhat more engaging and interesting plot make it slightly more tolerable than you may think. Alvin, Simon, Theodore, and the Chipettes are having fun on a luxury cruise when they end up stranded on a secluded island. Soon enough, they find out that they are not as alone as they thought.

6 Alvin and the Chipmunks Meet the Wolfman

Alvin and the Chipmunks started off as beloved cartoon characters and so it is only fitting for them to become features in their own films. Alvin and the Chipmunks Meet the Wolfman is a direct-to-video movie that was released in 2001. This animated film is the perfect family-friendly cartoon for the spooky season. After Alvin experiences terrifying nightmares, he reveals to both Simon and Theodore that their neighbor, Mr. Talbot, is the reason why. They then go on to investigate and ultimately try to uncover proof that Mr. Talbot is, in fact, a werewolf.

5 Alvin and the Chipmunks Meet Frankenstein

The charm of the animated Alvin and the Chipmunk movies puts this movie higher up on this list. Alvin and the Chipmunks Meet Frankenstein was the first direct-to-video Alvin and the Chipmunks film. In this film, the singing trio visit and get locked inside Majestic Movie Studios, a theme park that the group visits while on break from a concert. They end up encountering a monster at the “Frankenstein’s Castle” attraction. If you need a lighthearted, charming cartoon for the Halloween season, this one is a solid option.

4 Little Alvin & The Mini-Munks

Little Alvin & The Mini-Munks is not quite like any of the other movies in this franchise. It expands the universe beyond just Alvin, Simon, Theodore, and Dave, and introduces many more characters. This was a direct-to-video film that had the Chipmunks and the Chipettes staying with Dave’s friend La-Lu as he goes off to write a song. This movie brings new life to the story and is greatly enjoyed by critics and audiences, landing a decent 7.5/10 rating on IMDb.
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3 The Chipmunk Adventure

Alvin and the Chipmunks were characters on television before they made their iconic film debut in the movie The Chipmunk Adventure. In this animated comedy film, the Chipmunks and the Chipettes go head-to-head in a hot air balloon race across the world in search of dolls as proof that they did in fact reach that location. This movie is every last drop of family fun, competition, and adventure you could possibly ask for, making it one of the more enjoyable movies in the franchise.

2 Alvin and the Chipmunks: The Squeakquel

Who knew that an Alvin and the Chipmunks movie could have so much…girl power? The introduction of the Chipettes, another chipmunk trio, into the live-action movies successfully continued the popularity and momentum established by the first movie. In Alvin and the Chipmunks: The Squeakquel, Alvin, Simon, and Theodore’s music career as rising superstars comes to a halt when they are forced to return to high school. A Battle of the Bands competition to help out the school’s music program becomes their main goal, but their plans are hindered when Brittany (Christina Applegate), Jeanette (Anna Faris), and Eleanor (Amy Poehler), a group known as The Chipettes, emerge as their main competition.

1 Alvin and the Chipmunks

The rise of pop music sung by insanely high-pitched vocals was definitely an unforgettable trend in 2007. The first live-action of the franchise, simply titled Alvin and the Chipmunks follows the journey of Alvin, Simon, and Theodore as they come across aspiring music writer and producer Dave Seville. The group finds their unique talent as a tool to get them straight to super-stardom status. The sense of a found family is a prominent theme in this movie that takes it beyond just the musical comedy it is on the surface. In addition to that, Alvin and the Chipmunks is a really great movie to have on during the holidays or to just feel a sudden rush of nostalgia.

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