Alvin And The Chipmunks Movies in Order – All the Movies and TV Series You Didn’t Know

Some movies and characters remain a classic and the trio of Alvin, Simon, and Theodore from Alvin and the Chipmunks is the perfect example of that. They have transcended their animated roots to become cultural icons with a series of successful live-action/CGI hybrid films.

Yes, you heard it right. While we are aware of the popular Alvin and the Chipmunks movie franchise, what many of us aren’t aware of is the fact that the characters were initially popularized during the 80s for their series-based animated shows.

If you are a fan of Alvin and the Chipmunks and have been planning to watch the movies in order, we recommend that you follow through with this article for all the details.

Alvin and the Chipmunk Movies in Order

While we are on the topic of sorting out all the Alvin and Chipmunk movies and shows, we have managed to narrow down all the options that are available for you to go back and watch.

1. Alvin and the Chipmunks Original Animated Series (1983-1990)

Before gracing the big screen, Alvin and the Chipmunks first gained popularity on television with their original animated series that ran from 1983 to 1990.

The show was created by the dynamic duo of Ross Bagdasarian and Janice Karman and because it ran for 7+ years, it is safe to assume that the show was loved by the audience regardless of everything.

Like pretty much all the Alvin and the Chipmunks franchise movies, even the original animated version featured the misadventures of Alvin, Simon, Theodore, and their long-suffering guardian, Dave Seville. The animated series laid the foundation for the chipmunks’ enduring appeal, setting the stage for their transition to the world of cinema.

2. The Chipmunk Adventure (1987)

While the animated series featuring Alvin and his brothers was gaining traction, a new movie featuring them was released in 1987. The animated feature film was directed by Janice Karman and featured the chipmunks and The Chipettes engaged in a race around the world, competing in a hot air balloon to retrieve lost diamonds.

It was quite the adventure and the storyline and the overall direction showcased in the movie somehow made it a classic that people love watching, to this day. 

If you are one of those fans who grew up watching the animated series, watching the 1987 movie is probably a nostalgia that you never want to get over. The vibrant animation and the adventure-filled plot somehow keep this movie an iconic one through and through.

3. Alvin and the Chipmunks Meet Frankenstein (1999)

The third in the list of the Alvin and the Chipmunks franchise that deserves a shoutout is the 1999 release. This was a direct-to-video animated film directed by Kathi Castillo that features the staple main cast of Alvin, Simon, Theodore, and their guardian, Dave Seville.

The storyline unfolds when the Chipmunks and the Chipettes find themselves performing at a theme park, where they inadvertently become part of a stage show involving Dr. Frankenstein’s monster.

However, instead of being a “prop,” the chipmunks realize that it is a real-life monster but not a bad one. The only thing that the monster is on the outlook for is friendship and companionship from people. The film cleverly incorporates classic horror tropes into the narrative while maintaining a family-friendly atmosphere, which explains why it is so popular to this day.

4. Alvin and the Chipmunks Meet the Wolfman (2000)

A year after the release of the Frankenstein version, the audience was blessed with yet another rendition, which was “Meet the Wolfman.” This particular movie was also directed by Kathi Castillo, which explains why there was such a great storyline and links tied with the previous releases, making the whole watch even more exciting and fun.

This particular movie follows the life of the chipmunks when they find themselves entangled in a series of mysterious events that lead them to believe that their friend Theodore might be turning into a werewolf. As they navigate the challenges of trying to prevent Theodore from transforming during a full moon, a lot is unveiled about friendship and bonding.

It starts tense but the movie is one of those feel-good movies that you watch when you are feeling down and weathered. The film cleverly plays with werewolf lore, offering a unique twist that keeps the audience engaged while maintaining an age-appropriate level of suspense.

5. Alvin and the Chipmunks (2007)

The Alvin and the Chipmunk movies that we generally talk about in the passing started with this 2007 release. It was a live-action/CGI hybrid directed by Tim Hill and the aim was to introduce the famous chipmunk trip to a new generation of audiences.

If you have yet to watch the movie, it follows the mischief and adventure of Alvin, Theodore, and Simon who try to navigate their way into sneaking inside the home of a struggling musician and songwriter, Dave Seville.

This installment not only brought the classic characters to life with cutting-edge CGI but also featured a star-studded cast, including Jason Lee as Dave Seville. The box office success of this installment is a testament to how extensively popular the Alvin and the Chipmunk franchise is and always has been.

6. Alvin and the Chipmunks: The Squeakquel (2009)

The sequel to 2007 was primarily developed to beat the hammer while it was hot and capitalize on the success of the first movie’s release after a while. This one was directed by Betty Thomas and was another successful installment of the movie franchise.

This installment introduced female counterparts to the chipmunks in the form of The Chipettes—Brittany, Jeanette, and Eleanor. The addition of The Chipettes brought a new dynamic to the group, both musically and comically. What made this movie stand out was how it delved into exploring the characters of each chipmunk.

With a blend of humor, heartwarming moments, and catchy musical performances, the film solidified the chipmunks’ status as more than animated characters—they became cinematic sensations. Overall, like the previous 2007 movie, even the 2009 version was a huge success at the box office.

7. Alvin and the Chipmunks: Chipwrecked (2011)

The penultimate release in the Alvin and the Chipmunks franchise is the “Chipwrecked” version, which was released in 2011 and directed by Mike Mitchell. This particular movie follows the chipmunks and The Chipettes when they are accidentally marooned on a deserted island during a cruise.

Unlike the previous releases, this one explores a completely new experience and backdrop, which someone ended up being another huge success. The tropical backdrop was stunning and somehow the escapades, humor, and the adventures that the characters set out on made it an even more interesting watch.

Also, if you loved the musical performances from the prior movie, you are going to enjoy it in this one too. What sealed the deal with this movie was the introduction of adventure and exploration that were introduced in the movie.

8. Alvin and the Chipmunks: The Road Chip (2015)

The last in the list of the Alvin and the Chipmunks movie franchise is “The Road Chip.” The movie was directed by Walt Becker and instead of the same type of storyline, this one took a different route with the narrative focusing on a road trip.

The film explores the chipmunks’ journey to prevent their guardian, Dave Seville, from proposing to his girlfriend, potentially leading to a stepbrother who might threaten their close-knit bond. The elements of humor and musical performance remain static in this one too, so you won’t be missing that.

The road trip setting allowed for a series of hilarious misadventures and showcased the chipmunks’ ability to entertain in various environments. So, if you want to see Alvin and his brothers in their element, this is the perfect movie for it.

Cast and Character Guide

Now that we have a breakdown of all the Alvin and the Chipmunk movies, it makes sense that we also have to give you a rundown of the cast and character guide.

The Chipmunks

• Alvin – The charismatic and mischievous leader of the trio.
• Simon – The intellectual and sensible chipmunk.
• Theodore – The lovable and gentle member of the trio.

The Chipettes

• Brittany – The sassy and ambitious leader of The Chipettes.
• Jeanette – The intellectual counterpart to Brittany.
• Eleanor – The sweet and nurturing member of The Chipettes.

Human Characters

• Dave Seville – The Chipmunks’ adoptive father and manager. He is also a struggling musician and songwriter.
• Ian Hawke – The ambitious and often antagonistic music producer. His motives are what add conflict to the movie’s plot.

Besides these characters, you have a few guest appearances and movie-specific characters that have shown up throughout the years. However, if you are setting off to watch Alvin and the Chipmunks and want to get a basic rundown of the main characters in the movies, these are some of the most important ones.