How exactly do these chipmunks age relative to humans? The series seems to suggest that as babies they are already able to talk coherently yet are not too far away from the size of chipmunks in the real world, but that they rapidly grow to the size of human children.
Why does Simon complain to Alvin about not knowing certain things, such as how parenting works? Simon has never been a parent himself. Plus, there are some things he complains about that seem pretty hypocritical.
Are chipmunks the only animals that can take on anthropomorphic physical attributes and integrate into human society in this universe?
So much about the Chipettes is odd. First of all, they come from Australia. Chipmunks do not occur naturally there, so how did they get there in the first place? Are chipmunks native to Australia in this universe or did they come from imported pet stock, perhaps?
The Chipettes come to America, are hired - as little chipmunks - to do menial work, and build up a career as a successful musical group. They manage to live an independent, self-sufficient life in a tree house. Then, in "Help Wanted: Mommy", they find themselves needing adult guardians when the school they attend together with the Chipmunks finds out that they are orphans because of a rule that at least one parent must come to the school's parents' night. Now, how would one go about enforcing parental participation in parent-teacher conferences or similar events and if the school is so big on parental involvement, it would be extremely interesting to know how it slipped past them that the Chipettes had enrolled in the school without a guardian in the first place.
"That's completely unrealistic!" Oh, and talking chipmunks AREN'T?
There is also a curious dissonance between "Help Wanted: Mommy" and "Cinderella? Cinderella!". In the former episode, the Chipettes have been taken in by Miss Miller, whose initial approach to raising them involves babying them and imposing rules like having to wear skirts at least three inches below the knee. Of course, they are not happy, but they don't seriously rebel. By the latter episode, Miss Miller seems to have largely abandoned her former approach to parenting, yet Brittany outright rebels merely against being asked to help with a simple chore! Not only is this shift in her behavior peculiar, but given that until recently she and her sisters had lived independently in a neat little house of their own, wouldn't she have been used to pitching in around the house - surely Jeanette and Eleanor didn't do all the cleaning up there?
Isn't it disrespectful to call your adopted father by his first name? Shouldn't Dave feel offended? After all, he raised them.
He is their adoptive father and he did not raise them from the earliest infancy, so calling him "Dad" may not have come naturally. Especially since he's a different species than they are.
In one episode, Dave reads Treasure Island to the chipmunks, and we the viewers see it acted out in a chipmunk version. But if you've read the book, you know it doesn't really go like the version we see in the episode. So... did Dave change the plot for some reason? Or does this cartoon take place in an alternate universe where this new version is how Stevenson wrote the book?
Treasure Island is in the public domain, meaning anyone can write it in whatever way they want. The book he had couldve been a version by someone else.
The reenactment of the story that we saw in the episode could easily have been how the boys imagined it while they were listening, projecting themselves onto the characters, rather than an accurate reflection of what Dave read to them. Or the story-reading session could be seen as a framing device for a performance of a version of the classic tale by the characters of the show.
Live Action Films
In the first film, Simon got his glasses from a toy Santa. Yet in the second movie when we introduce the Chipettes, Jeanette is already wearing her glasses, with no explanation of how she got them. What's with that? What makes this even more confusing is that both cases were before they gave the Chipmunks their trademark clothing.
In the first film, how does Alvin inhaling air from the balloon make his voice deeper as he gloats "Major rock stars!", instead of making his voice a lot higher?
It's just a gag. The Chipmunks' normal speaking voices sound like Helium Speech, so actually breathing helium is ironically depicted as making them sound human-voiced. The alternative would've been making his voice ultrasonic, which the audience wouldn't be able to hear at all.
One of the plot points in the sequel is that Ian tries to push Eleanor and Jeanette into the background so Brittany can have the spotlight. This is treated as a bad thing. The headscratcher is that this is how they ALWAYS perform anyway; Britanny in front, Eleanor and Jeanette as backup.
Most likely because they want to have equal fame shared no matter who's in front of the spotlight or in back. They don't want anybody demoted.
Why did they feel necessary to change the lyrics of "Uptown Funk" in The Road Chip from "Fill my cup, put some liquor in it" to "Fill my cup, put some water in it" when the very next scene is Suggs explicitly drinking liquor and getting absolutely hammered?
Because even if a particular cover is produced for a movie scene, Chipmunks music is still marketed mainly for kids.