In one episode where Alvin was learning to ski, but ignoring Simon's instructions, he ends up tumbling down and creating a giant snowball, which is heading toward Simon and Theodore:
(Theodore runs around in a panic) Simon:(just stands there) Why can't he just listen for once?
The Running Gag with T-shirts the episode where Alvin and Simon help Theodore on his history test. The first is when Columbus (Alvin) arrived. Later the pilgrims came and offered T-shirts to the two indians already wearing the shirts Columbus gave them.
Then in Custard's Last Stand.
Alvin as Custard: How about some T-shirts, chief? Simon as Sitting Bull: No more stupid T-shirts! Alvin as Custard: Okay. Then how about some party favors? Whoopie Cushions? Simon as Sitting Bull: Let's charge him! Alvin as Custard: No problem. I take credit cards. Simon as Sitting Bull: No! We charge you!
From the episode "Snow Wrong":
Brittany: Nobody, but nobody calls my sister a jerk!!! Jeanette: Uh... but, you do all the time... Brittany:That's different!
From "Thinking Cap Trap":
Host: Alvin, what is syntax? Alvin: Syntax...A tax the church collects from sinners?
From "The Gang's All Here," Jeanette falls down while roller skating, bringing Brittany down with her.
Jeanette: Sorry, Brittany. I tell my feet where to go, but they just don't listen to me.
Brittany: (Grabs Jeanette's foot) GET OFF THE RINK!!!
Jeanette: But... maybe they'll listen to you instead.
When Dave first meets the Chipmunks and lays down how things are gonna be run around his house. When..
Alvin: Lemme ask you: have you ever written a song before? Dave: Yep. Alvin: And...is that your music stuff outside? Dave: Yep. (Thunder rumbles reminding Dave that his songwriting equipment is soaked in the rain)... OH, NO! Simon: Hurry back!
For The Squeakquel:
That "purr" sound Simon makes in the second movie when he sees Jeanette.
When Alvin runs into Brittany at the lunch table
Alvin: I just wanted to warn ya about Ian.
Brittany: What? You should be grateful to him and you broke his heart!
Alvin: Oh, really? How do I put this gently? He doesn't have one. Oh, and one of the things he did for us was put us in a cage!
Simon drastically overestimates Ian's intelligence.
Simon: All right, now the third number is always the toughest to crack... I'll assume it's a prime number, but we can't assume-
Jeanette: Simon... the first two numbers were one... I'm gonna go with one. () Ah, it worked!
When Alvin tries to get An amnesiac Simon's attention
Alvin: "SIIIIIIIIIIMOOOOOOOOOON!" Brittany: "Alvin? You’re starting to sound like Dave." Alvin: “NOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO!!!!!!!" —>Cut to another part of the island as Dave wakes up from hearing the Alvin's echoing scream. Then shrugs and lays back down on the manmade nest. Then Ian tries to nab Dave's macaroni necklace that Theo made him. But Dave, without even opening his eyes, swats his hand at Ian.
After the kite incident and the 6 Chipmunks are drifting away at sea, Alvin has this to say:
Alvin: In retrospect, this was a bad idea.
As Theo's floating on a donut as a inter tube at the end of the kite string
Theodore: I don't think I can make it much longer! I'm so hungry! Just one bite? Simon: No. Theodore: A nibble? Simon: No nibbles! Theodore: Could I at least lick the glaze? Simon: The glaze is what's keeping you alive, Theodore! It's high-fat content is creating a water-proof barrier. Theodore: I'm gonna starve to death! Jeanette: Actually, there are many ways that would kill you before starvation: dehydration, sunstroke— Eleanor: [gasps] An island! Jeanette: No, an island would probably be helpful. So if you see one you should definitely say something. Brittany: Uh, Jeanette? [gestures towards the island] Jeanette: Oh!
When the exhausted chipmunks arrive on the island
Alvin: We're alive! We're alive!
Brittany: Good! 'Cause now...I'M GOING TO KILL YOU!
Simon: Guys, guys, guys! NOBODY is killing anybody! [grits his teeth at Alvin] No matter how much he deserves it.
Alvin: Thanks, Si. Though I could've done without the passive aggression.
The terrified expression Alvin has on his face as the furious Brittany looms over him before Simon comes between them just sells it.
When Simon demonstrates a magnifying glass by using his specs to use the sun's light. When Jeanette compliments him on it being impressive, Simon, distracted, redirects the beam to his foot.
Simon: HOT! HOT! HOT! [limps around the beach & jumps into the ocean, then sighs in relief] Ah...that's better...
Gets an even louder reprise when Dave finds out the boys left the house, seeing them on TV performing in the Mardi Gras parade
Miles is holding a coke can in his hand when he sees Ashley for the first time, he gazes so smitten that he unwittingly spills his can of coke—all over Theodore!
This little exchange
Dave: I thought you were mature enough to take care of yourselves! Alvin: That's insulting. We're very mature! (A loud fart is heard) Theodore: Heheh! Sorry. Pizza toots.
The first confrontation with Agent James Suggs after Theodore causes the cargo pets to go loose on the plane. Suggs then reveals to the Chipmunks that he hates them for one of their songs causing his girlfriend dump him in favor of his fandom towards the Chipmunks.
James Suggs: You provided the soundtrack to my heartbreak! But now it's payback time! I'm putting you three on the No-Fly List! Chipmunks: What?! But we gotta get to Miami! James Suggs: See, I'm an air marshall. I'm all-powerful, I'm all-seeing and I'm all-knowing. Alvin: Then you obviously know that you just made that entire speech with your tie in a cup of coffee. (Suggs pulls his tie out of the mug. Miles tries not to laugh.) James Suggs: D'oh! I'll be back in two minutes. Alvin: You also still have a little parrot poop on your shirt. James Suggs: 10 minutes. And one more thing: Don't even think about leavin'. I have a very particular set of skills. Skills that I've acquired for a very long— Alvin: You just put your hand on an ink pad. (Suggs lifts his hand, his palm with ink on it.) James Suggs: 15 minutes. (leaves)
As Suggs chases the Chipmunks and Miles out of the bar saloon!
Suggs: I WILL GET YOU, CHIPMUNKS! I WILL STUFF YOU! I WILL HUNT YOU DOWN! I WLL POUNCE ON YOU! I WILL—(runs straight into a road sign) Alvin: Oooh! That's gotta hurt! Suggs: ...take a little nap... (passes out)
The Chipettes spend most of the movie on a tour to judge American Idol, to the the Chipmunks' (well, mainly Alvin's) jealousy.
Brittany (on TV): You're going to Hollywood! Alvin: Aw! I always wanted to say that!
Later, Alvin gets his chance to say the phrase as he rallies the girls for his plan to make things up with Dave.
When Suggs confronts the Chipmunks in New Orleans.
(Theodore looks in a hat set for tips) Theodore: Alright! A tater tot! Looks like our luck is finally turning around! Suggs: It's not. Simon: Oh, no! Suggs?! Suggs: Hello, boys! Simon: How'd you find us?! Suggs: Ahaha! I'm an air marshal! Law enforcement's my life. Now we can either do this the easy way or the hard way. Alvin: My brothers and I would like to discuss our options! Suggs: You only got one option: Chipmunk Jail! With tiny little bars, a tiny little barbed wire fence, a tiny toilet, and a tiny yard where you can lift your tiny little weights! Theodore: It sounds adorable.
Suggs is equipped with a yellow cab, to his extreme disappointment.
Suggs: Are you kiddin' me right now? Ya know what this is? This is a roller skate with wheels! Rent-A-Car Employee: Pretty sure roller skates come with wheels. Suggs: Ah! (snatches his rental agreement and gets angrily into the car) It's like Tweety Bird! Rent-A-Car Employee: Buckle up! Suggs: SHUT UP! THIS IS LIKE DRIVING A PARAKEET!!