Alvin has a harmonica solo at the famed carnegie hall. But there is a slight problem-- Alvin has given his harmonica to a sick boy!

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.

When they can't determine when their birthday is, the Chipmunks set out to find their mother, Vinny, who abandoned them as babies.

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.

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.

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.

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Simon, Theodore and Alvin become involved in a jewel-smuggling operation while their guardian is away.