It was 2009. The world was obsessed with "Single Ladies," the Black Eyed Peas were everywhere, and for some reason, we all decided that high-pitched rodents singing pop covers was the peak of cinema. Honestly? It kind of was. When looking back at the cast of Alvin and the Chipmunks: The Squeakquel, it’s easy to dismiss it as just another kids' movie. But if you actually dig into the roster, it’s low-key stacked. You have legendary comedic actors, rising stars who hadn’t even hit their peak yet, and a voice cast that basically defined a specific era of Nickelodeon and Disney royalty.
The movie had a massive job. It had to introduce the Chipettes without making them feel like cheap knock-offs. To do that, the producers didn't just grab random session singers. They went for names. Big ones.
The Human Side of the Chaos: Zachary Levi and Jason Lee
Most people remember Jason Lee as Dave Seville. That's a given. He’s the face of the franchise. But in the second film, Lee’s role is actually pretty limited. He spent most of the movie "in a body cast" in a Paris hospital because of a stage accident. This wasn't just a plot point; it allowed Jason Lee to film his scenes quickly so he could balance other projects, like the tail end of My Name is Earl.
This opened the door for Zachary Levi.
Before he was Shazam or the voice of Flynn Rider in Tangled, Levi played Toby Seville, Dave’s awkward, gaming-obsessed cousin. It’s a weirdly specific performance. He’s basically the "nerd" archetype of the late 2000s—hoodies, messy hair, and an obsession with Gears of War. Levi brought a different energy than Lee. While Dave was the frustrated parent, Toby was the guy who barely knew how to take care of himself, let alone three chipmunks.
Then you’ve got David Cross returning as Ian Hawke. Cross has been very vocal over the years—often in a hilarious, self-deprecating way—about his time in these movies. He plays the villainous, disgraced music mogul with a level of commitment that feels way too high for a movie about talking animals. He’s living in the basement of JETT Records, wearing a giant plush bird suit at one point. It’s physical comedy at its most desperate, and Cross nails it.
The Chipmunks: The Voices Behind the High-Pitch
You might think the voices of Alvin, Simon, and Theodore are just some guys in a booth being sped up. Well, technically, yes. But the cast of Alvin and the Chipmunks: The Squeakquel features some heavy hitters in the voice department.
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- Justin Long returned as Alvin. He brings that "cool guy" arrogance that makes Alvin both lovable and incredibly annoying. Long was in his "Mac vs. PC" commercial prime here, and his voice carries that specific snark.
- Matthew Gray Gubler voiced Simon. At the time, Gubler was becoming a household name thanks to Criminal Minds. His natural voice is quite deep, so hearing him translated into the intellectual, nerdy Simon is always a trip.
- Jesse McCartney voiced Theodore. This is the one that surprises people. The "Beautiful Soul" singer and teen heartthrob was the baby of the group. McCartney actually has a lot of voice acting experience (he's Roxas in Kingdom Hearts!), and he brings a genuine sweetness to Theodore that keeps the character from being too one-note.
The process of recording these is actually pretty grueling. The actors have to speak their lines slowly so that when the audio is sped up (a process called "varispeeding"), the pitch goes up but the timing remains natural. If they spoke at a normal pace, the chipmunk versions would sound like they were on 2x speed.
Enter the Chipettes: The Powerhouse Trio
The real draw of the Squeakquel was the introduction of the Chipettes. This is where the cast of Alvin and the Chipmunks: The Squeakquel gets really interesting from a "where are they now" perspective.
Christina Applegate played Brittany. She’s the leader, the diva, and the counterpart to Alvin. Applegate was fresh off Samantha Who? and brought a specific comedic timing that made Brittany more than just a pink-wearing caricature. She made her ambitious.
Anna Faris voiced Jeanette. This was peak Anna Faris era. She was the queen of the Scary Movie franchise and The House Bunny. She gave Jeanette that clumsy, shy, but deeply intelligent vibe. If you listen closely, you can hear that signature Faris breathiness even through the pitch-shifting.
Amy Poehler played Eleanor. Yes, Leslie Knope herself was a Chipette. Poehler replaced the original 80s characterization with something a bit more spunky and athletic. It’s a small role in the grand scheme of her career, but it adds to the "how did they get all these people?" factor of the movie.
Supporting Players and Cameos
The film didn't stop with the main six. Because the plot revolves around a "Battle of the Bands" at a high school, we got a bunch of character actors filling out the faculty and student body.
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Wendie Malick (from Just Shoot Me! and Hot in Cleveland) plays Dr. Rubin, the school principal who is a secret Chipmunks fangirl. Her deadpan delivery when she shows off her "Alvin" tattoo is one of the better adult-leaning jokes in the movie.
There's also Kevin Schmidt as Ryan, the high school jock who bullies the chipmunks before eventually (spoiler alert) finding some common ground. It’s a classic 2000s teen movie trope shoved into a CGI animal flick.
Why the Voice Acting Actually Matters
It’s easy to joke about these movies, but the chemistry between the voice actors is what made the Squeakquel out-earn the original at the box office. They weren't just reading lines; they were building personalities that had to compete with a lot of loud, colorful CGI.
Think about the scene where the Chipettes first meet Ian Hawke. He manipulates them by preying on their desire for stardom. The way Applegate, Faris, and Poehler play that—ranging from naive excitement to subtle hesitation—is actually decent character work.
The Music: A Cast Achievement
We can't talk about the cast without talking about the music. While the actors provided the speaking voices, the singing was a mix of their performances and professional vocalists like Ross Bagdasarian Jr. and Janice Karman (the owners of the franchise).
The soundtrack for the Squeakquel actually hit number 6 on the Billboard 200. It beat out some serious "human" artists that year. When you hear the Chipettes' version of "Single Ladies (Put a Ring on It)," you’re hearing a blend of the celebrity "character" and the classic Chipmunk sound engineering. It’s a weirdly complex production for something meant to entertain seven-year-olds.
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Common Misconceptions About the Cast
A lot of people think Ross Bagdasarian Jr. (the son of the creator) voiced the chipmunks in the live-action movies. He didn't. He and his wife Janice Karman voiced them for decades in the cartoons, and they acted as consultants and producers on the film, but the studio wanted "Hollywood" names for the big-screen reboot.
Another thing? Jason Lee wasn't replaced because he hated the sequel. There were rumors for years that he left because the script was "beneath him," but the reality was much more mundane: scheduling and a desire to give the "Toby" character a chance to lead the B-plot. He came back for the third and fourth movies, so clearly, there was no bad blood.
How to Explore the Cast Further
If you’re looking to dive deeper into this specific era of pop culture or the work of these actors, here’s what you should actually do:
Check out the "behind the scenes" featurettes on the physical media or certain streaming platforms. Seeing Justin Long and Matthew Gray Gubler in the recording booth is genuinely fascinating. They have to act with their whole bodies to get the energy right, even though only their voices are being recorded.
Also, if you're a fan of Matthew Gray Gubler, compare his Simon voice to his work in 68 Kill or Criminal Minds. The range is wild.
For Zachary Levi fans, this movie is a time capsule. It’s the bridge between his cult-classic status in Chuck and his eventual superstardom. You can see the seeds of his physical comedy style here.
If you’re watching with kids (or just for nostalgia), pay attention to the dialogue. There are a lot of ad-libs, especially from David Cross, that definitely weren't in the original script. He has a way of making "kids movie villain" feel like a legitimate Shakespearean tragedy.
The cast of Alvin and the Chipmunks: The Squeakquel represents a very specific moment in Hollywood where every major comedic talent was being funneled into these massive CGI-hybrid franchises. It’s a snapshot of 2009 talent, from indie darlings to sitcom legends, all coming together to sing "Hot N Cold" at a fake high school concert. It shouldn't work, but somehow, it kind of does.