A charaltan chipmunk named Harry claims to be Alvin, Simon and Theodore's long lost uncle and says he will have them see their mother as soon as they make enough money. The Chipmunks later not only find out that Harry is not their uncle but also the money he has them making is for a carnival strongman who he has owed for a long time.
The Chipmunks make up a singing telegraph service to help buy some golf clubs for Dave's Birthday. But when Theodore loses the addresses, the boys are sent on a birthday mission, for a 100 dollar bonus. Except, that when Theodore wrote the number he wrote it upside down, so the Chipmunks end up going to the wrong house and are tricked into doing some different pranks for some highschoolers who are bored.
The boys enter a contest so that they can win a chance to sing with Dolly Parton. But, the only way they can win is if they are from Nashville. The boys enter the contest anyway, but make an enemy when they win. The person who got second place in the drawing is determined to prove that the Chipmunks aren't from Nashville, and win his chance to sing with Dolly Parton.
Alvin demands a short trip away from obsessed fans who begin following him everywhere he goes. So, the Chipmunks go for a picnic out in the woods, only to be found again by their fans. Alvin runs off into the woods, and runs into a wild chipmunk. He decides to change places with the chipmunk, and he stays in the chipmunk's tree, while the wild chipmunk takes his place. All goes well until the real Alvin is caught by a hunter that holds him hostage. Simon, Theodore, and the wild chipmunk must save Alvin before it's to late.
Dave drags the Chipmunks unwillingly on a camping trip in the great out doors. When they finally arrive, the Chipmunks discover large footprints and think they are being followed by Bigfoot. Eventually they build a treehouse for Dave, when he falls and injures himself badly, and Alvin and Simon go in search for Big Foot.
The Chipettes are looking forward to be spending Valentine's Day with the Chipmunks. Simon and Theodore are also looking forward in spending the day with them, except Alvin. He is afraid of being crushed again due to the fact that a girl he once had a crush on broke his heart on Valentines. In order to rebuild his confidence, Simon makes a tape for Alvin to listen to while he sleeps. Without realizing, the tape hypnotizes Alvin into believing he is a Casanova named Captain Chipmunk while sleepwalking and is finally able to gather up the courage to ask Brittany... although once he awakens, he cannot remember. So, once he finally gathers the courage to ask her, she rejects him, since she has already been invited by the wonderful, dashing, charming Captain Chipmunk. But of course, the special ends with both Alvin and Brittany finally going together and being voted King and Queen Valantine.
The Chipmunks and Chipettes audition to be in a play on Snow White. After the audition, the director selects Brittany for the role of Snow White. However, the director's demanding daughter, Tara-Marie, who had flopped big-time in the auditions for the title role, plans to make her father reconsider.
Brittany tries to join the Sisters, a club of the best-dressed, most popular girls in school. But in order to do so she has to avoid her own sister Jeanette, whose clumsiness and unpopularity would destroy her chances of getting into the club. Since she and Jeanette are working on a science project that involves taking care of a baby pig, this leaves Jeanette to do the project alone.
The origin of the Chipettes is revealed when they are reunited with their old Australian friend Olivia, which prompts the singers to remember their younger days when they were just little tiny baby Chipettes living in Miss Grudge's orphanage in Australia with Olivia not trying to have a career, only trying to survive. The Chipettes successfully make their way into the United States, yet they find out the hard way that getting there is only half the battle. After taking various odd jobs in middle management, the Chipettes travel across the country to California. There, the girls manage to find a famous record producer who after hearing their first song, gives the Chipettes the break they were looking for.
The Chipette's successfully make their way into the U.S.A., yet they find out the hard way that getting there is only half the battle. After taking various odd jobs in middle management, the Chipette's travel across the continent to California. There the girls manage to find a famous record producer who after hearing their first song, gives the Chipette's the break they were looking for. The rest of course, is history.
While the Chipmunks are on tour in Switzerland, Brittany is depressed about the Chipettes’ relative lack of fame. So Alvin arranges for the ultimate Swiss publicity stunt: the gang will climb the Matterhorn and the Chipettes will give a concert at the mountain’s peak. But they soon become trapped in an avalanche.
When Dave wins a producer’s award, a wax figure of him for a Hall of Fame is delivered, unbeknownst to the Chipmunks. While playing ball in the house, which Dave strictly forbid before he left, Alvin hits the wax figure of Dave with his ball, toppling him over. After watching a soap opera, they think he has developed a strange disease called "Zomboid rigidosis" and begin retelling his life for him, hoping he will snap out of it.
After the Chipettes rig Miss Miller’s poker game, she takes them to Las Vegas and becomes a compulsive gambler. She is finally cured when another gambler defeats her in a high-stakes game of blackjack, only to return his winnings after she learns her lesson. The other gambler turns out to be David Seville, the Chipmunks' father, in disguise.
When Brittany refuses to do her chores, Miss Miller tells her that she must mop if she wishes to go to a dance that night. Brittany falls asleep and dreams she is Cinderella. She awakens to find a new party dress and Miss Miller mopping half the floor for her. Brittany realizes she is not living with the wicked stepmother after all.
Dave starts feeling old on his birthday, so the Chipmunks set him up on a date with Marcy Apple, his old college sweetheart. But she was soon going to be married, so he goes out with Bambi, her younger sister (who is young enough to be his daughter) and they soon begin seeing each other regularly, to the Chipmunks’ chagrin.
A wild ride on a merry-go-round sends the Chipmunks back to 1962. They meet a younger Dave. Without the boys' help in winning a band contest, he will spend his life as an accountant. When they are spun into the present, Alvin isn't sure whether he visited the past or bumped his head in a fall off the merry-go-round.
Alvin "borrows" Dave's new bike, and while he is out riding he accidentally hits Brittany who is out roller skating. The bike is ruined, and something is wrong with her skates. They each blame each other, and Alvin demands Brittany pay for Dave's bike, while she insists he pay for her roller skates. All of this brings us to court, where Brittany and Alvin, ignoring the "TRUTH" part in justice, face off in a "who can tell a better lie about what happened" court battle.
Theodore goes on a diet so he could go on a date with a pen pal, who is also one of Alvin's biggest fans. Things go wrong when Alvin finds out that Theodore's date is actually the daughter of a famous film director. Alvin then takes her out instead, breaking Theodore's heart. In order for Alvin to make it to his play and the date, Alvin gets Theodore to switch back and forth to his play and on his date.
The boys have to paint the garage after they got spray paint on the walls while repainting their bicycles. Simon and Theodore feels bad because they always have problems with Alvin's ideas. Later Alvin have them to go to a mansion of a now dead criminal. Alvin is convinced that a never found loot from a bankrobbery is still hidden there. They go because Alvin promises to paint all the garage if he's wrong, but they feel a little bad with Alvin.
After years of scrimping and saving, Dave is finally able to afford their own vacation cabin. Alvin hears that Robby Leach, the host of the show “Lifestyles of the Truly Fabulous” lives nearby. Alvin tries to get Leach to interview him, and at the same time he makes a few quick changes to Dave's cabin.
Alvin gets a registered letter from the Publishing Warehouse stating he is a winner. He either can take $500 or the mystery prize (which might end up to be a million dollars or nothing more than a free lunch), but has to call by 6:00 p.m. to decide. So Simon uses his experimental time machine to get a glimpse into two futures for them all, dependent on whether Alvin accepts the mystery prize or the $500 cash prize.
Miss Miller & the Chipettes are vacationing in Hollywood, as well as Miss Miller reuniting with her girl singing group, The Thrillers. In the lobby of the hotel, they learn that some producers are looking for new acts on their new show, "Girls of Rock & Roll". Sneaking behind each others backs, the Chipettes along with Miss Miller & The Thrillers try to get an audition set @ the hotel restaurant. The producers chose both of them (without the other knowing). When each group arrives @ the studio, they perform "Boogie Woogie Bugle Boy". But just as they confessed to each other that they were auditioning, the producers find a punk girl band touring the studio & hired them over both acts!
Theodore encounters a stray kitten that entered through an open window in the house. He and the boys take an instant liking to the kitten, and after some compromising, they name the kitten Cookie Chomper III, and after Dave is cured of his allergy to cats, he comes to like the kitten as well. After Cookie Chomper gets run over, the boys have a hard time dealing with it. Eventually, they get a new pet, a puppy they name Lilly.
Alvin lies to his classmates that he will be singing on stage with Michael Jackson. As Alvin tries to find Michael in order to see if it really is possible he could perform with him, he meets up with the big star's manager. To Alvin's surprise, this so-called manager is a homeless man looking to find a place to stay.
Simon is frustrated being the smartest member of the family. He invents a cap that helps Dave and his brothers become smarter. Simon is so confident with his family’s new smarts that he signs them up to be on a genius game show. But before he could give his family another boost of the thinking cap, he loses it.
When Dave leaves on a trip to Europe leaving the kids home with Miss Miller, Alvin starts competing with Brittany on the video arcade game, "Around the World in 30 Days". This grabs the attention of two diamond swindlers, who trick them into going on a balloon race, trading dolls filled with diamonds for dolls filled with cash.
A documentary special look of the Chipmunks' past throughout the decades. Will Smith hosts this special.
Alvin wants to join a gang that is well known for playing pranks on Halloween. One target they wish to pull a prank on is a boy with a deformed face who Theodore befriends.
The Chipmunks celebrate Thanksgiving with the family. They are also involved in a Thanksgiving play. But instead of getting the jobs they normally would be good at, the teacher decides to try something new with them. She gives the job of costume designer to Alvin, set technician to Theodore, and the starring role to Simon.
Alvin finds out that his Grandpa was the original Easter Chipmunk, and tries to sue Mr. Hoppity, the Easter Bunny for the rights.
While the Chipmunks are working in a famous movie studio park called Majestic Studios in a singing attraction, the real Dr. Frankenstein comes to work in the studio's most famous attraction, Frankenstein's Castle. After Alvin drives a crazy bus chase, they miss their next performance and get locked in the studio after closing time. Dr. Frankenstein figures the castle is not scary enough so he re-builds the real Frankenstein. IT COMES ALIVE! So it finds the boys and starts a wild and scary adventure!
Alvin thinks of himself as an expert on spooky stuff such as vampires and werewolves, so when a mysterious stranger moves in next door, Alvin's convinced he's a werewolf. Then, when Theodore gets bitten by a "dog", he starts chewing socks, eating meaty stuff, and is a lot faster, even Simon thinks something's not right. But at the moment, he's more like a werepuppy. They now have to find a way to cure him before the next full moon – during the school play, "Dr. Jekyll and Mr. Hyde" – or else Theodore will become a werewolf – forever!
Join the Chipmunks and Chipettes, as you've never seen them before, as they spend a magical weekend at Lalu's cottage.
Dave Seville meets Alvin, Simon, and Theodore for the first time.
Playing around while aboard a cruise ship, The Chipmunks and The Chipettes accidentally go overboard and end up marooned in a tropical paradise. They discover their new turf is not as deserted as it seems.
Through a series of misunderstandings, Alvin, Simon and Theodore come to believe that Dave is going to propose to his new girlfriend in Miami... and dump them. They have three days to get to him and stop the proposal, saving themselves not only from losing Dave but possibly from gaining a terrible stepbrother.
In this story, Alvin finds himself center stage as a Scroogelike little chipmunk.